Vacation Home Rentals By Owner In Holmes Beach, FL

The Black Pearl by Exclusive Vacations brVRC23-000114br brExperience luxury and coastal elegance at The Black Pearl, part of our Exclusive Collection. This stunning black and white designed beach home offers a private black-bottom infinity edge pool and panoramic Gulf views. Located within walking distance of the pristine beaches of Holmes Beach and just steps from the free island trolley, this four-bedroom, five-and-a-half-bathroom home offers the ultimate Florida vacation experience. Perfect for families or groups seeking opulence, relaxation, and adventure, The Black Pearl provides guests with a premium stay and exclusive amenities. brbrHighlights br• 2-minute walk to the Beach Access br• 4 Bedroom / 5.5 Bath br• 4 Kings, 1 Queen sleeper sofa br• Corn Hole and Ping Pong br• Resort Style 360 Infinity Edge Pool and Spa br• Rooftop Deck and Panoramic Beach Views br• Outdoor Grill and Dining Area br• Dog Friendly with host approval br• Walking Distance to Downtown Holmes Beach Shopping and Dining br• 4 Parking Spaces brbrExclusive Amenities br• 6 Seat Club Car Cru Golf Cart for Guest Use br• Luxury Beach Bikes for Guest Use br• Luxury Beach Chairs and a Beach Cart for Guest Use br• Upgraded Bed and Bath Linens and Toiletries br• Portable Pack and Play br brEnjoy your private outdoor oasis featuring a 360 Infinity edge infinity pool, a rooftop deck with a spa, fire-pit, sweeping beach views, and an outdoor seating area perfect for sunset cocktails. The outdoor kitchen and grill create the perfect setting for poolside barbecues, while fun outdoor games like corn hole and ping pong keep everyone entertained. The house includes a luxury six-seat golf cart and four beach bikes, making exploring the island effortless and stylish.br brThe bright, open living area offers a tranquil retreat after a day at the beach, with inviting sofas, modern artwork, and abundant natural light. The gourmet kitchen features custom cabinets, stainless steel appliances, sparkling countertops, and a large island with seating, ideal for preparing meals and entertaining. The dining room provides beautiful views of the tropical landscape, perfect for family dinners or celebrating special occasions. br brEach bedroom is designed for ultimate comfort and privacy. The primary suite features a plush king bed, spacious ensuite with a walk-in shower, and deluxe linens. The remaining bedrooms all have king beds and private ensuite bathrooms with walk-in showers, ensuring restful nights for everyone. An additional bathroom with a tub and shower combination is located on the third floor. The den includes a queen sofa bed, providing extra sleeping space, and a washer and dryer is available for added convenience. brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower  br• Second Bedroom: King bed, ensuite with walk-in shower  br• Third Bedroom: King bed, ensuite with walk-in shower  br• Fourth Bedroom: King bed, ensuite with walk-in shower  br• Bonus, Den: Queen sofa bedbr brGuests enjoy an outdoor shower, upgraded linens, and toiletries, along with complimentary beach chairs, beach cart, and bikes. The prime location steps from the trolley stop, allows easy access to all seven miles of Anna Maria Island beaches, shopping, dining, and outdoor adventures. br brBook your stay at The Black Pearl today and immerse yourself in a perfect blend of luxury, outdoor fun, and island adventure. From sunset sails to dolphin sightseeing, and beachside lounging to exploring historic Bean Point, this home offers everything you need for an unforgettable Gulf Coast vacation. Pack your sunglasses and flip-flops and make The Black Pearl your island getaway. Reserve now and create lifelong memories! br brbr- brThis home is managed by AMI Locals, an Anna Maria Island property management company. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Rental Policies for full details. brbr4 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrUse of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our AMI Locals Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Beautiful designer luxury home with Golf Cart, Bikes, Pool and Spa, Rooftop!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$249.2

VRC16-000498brbr2BR · 2BA · Sleeps 4 · Jan 2025 Remodel · Shared Heated Pool & Spa · Outdoor Bar · Gas Grill · Pet-Friendly ($150 Fee) · Walk to Beach · Festival Grounds Nearby · 1 Parking Space · For Sale — Showings with 24-Hr NoticebrbrImportant before booking: Pool Party North is currently listed for sale. Occasional showings may be scheduled during your stay with a minimum of 24 hours notice. If that's a concern, worth knowing before you book.brbrCompletely remodeled in January 2025 — new kitchen with butcher block countertops and modern appliances, upgraded bathrooms, and all-new furnishings throughout. The result is a fresh, well-configured two-bedroom duplex in Holmes Beach where the indoor updates match the outdoor setup.brbrThe shared backyard is the centerpiece. A heated pool and spa sit within lush tropical landscaping. The outdoor bar has a gas grill, sink, prep area, dining table, bar stools, and chaise lounges — a complete outdoor entertaining setup that guests consistently describe as the highlight of the stay. It's private, well-shaded, and genuinely resort-level for a duplex property.brTwo bedrooms sleep four. The primary suite has a king bed. The second bedroom has a queen bed. Two full bathrooms. The kitchen is fully equipped for meals at home. In-unit washer and dryer. High-speed WiFi included.brbrThe beach is a short walk. Local restaurants, cafés, and shops are within easy walking distance. The free AMI trolley stops nearby. The property is within walking distance of the Anna Maria Island festival grounds — making this a strong base for guests visiting during the island's popular events and markets.brbrPet-friendly with a $150 non-refundable fee. One parking space included.brbrPool Party North requires a one-week minimum stay.brbr*Final payments are due 60 days prior to arrival payable by personal check or Echeck (which will incur a $1.00 processing fee) we do takebrcredit cards for final payment with a 3% fee on the balance due

Pool Party North · Pool & Spa · Updated Jan 2025

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$325.91

VRC16-000497brbr3BR · 2BA · Sleeps 6 · Jan 2025 Remodel · Shared Heated Pool & Spa · Outdoor Bar · Gas Grill · Pet-Friendly ($150 Fee) · Quartz Kitchen · Walk to Beach · Festival Grounds Nearby · 2 Parking Spaces · For Sale — Showings with 24-Hr NoticebrbrImportant before booking: Pool Party South is currently listed for sale. Occasional showings may be scheduled during your stay with a minimum of 24 hours notice. If that's a concern, worth knowing before you book.brbrCompletely remodeled in January 2025 — new kitchen with quartz countertops and stainless appliances, upgraded bathrooms, and all-new furnishings throughout. Pool Party South is the larger side of the duplex — three bedrooms, two bathrooms, sleeping six in proper beds across a king, another king, and a queen.brbrThe backyard is shared with the North side and is the centerpiece of both units. A heated pool and spa sit within lush tropical landscaping. The outdoor bar has a gas grill, sink, prep area, dining table, bar stools, and chaise lounges — a complete outdoor entertaining setup that guests consistently describe as the highlight of the stay.brbrThe kitchen is fully equipped for meals at home. The open living and dining area is well-configured for a group of six. High-speed WiFi included. In-unit washer and dryer.brbrThe beach is a short walk. Local restaurants, cafés, and shops are within easy walking distance. The free AMI trolley stops nearby. The property is within walking distance of the Anna Maria Island festival grounds — making this the right base for guests visiting during the island's popular events and markets.brbrPet-friendly with a $150 non-refundable fee. Two parking spaces included.brPool Party South requires a one-week minimum stay.brbr*Final payments are due 60 days prior to arrival payable by personal check or Echeck (which will incur a $1.00 processing fee) we do takebrcredit cards for final payment with a 3% fee on the balance due

Pool Party South · 3BR · Pool & Spa · Updated Jan 2025

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$626.02

What You'll Love About This Home:brbrLocation! 3 Blocks to the Beach!br4 Bedrooms / 4 Bathroomsbr3 King Beds, Two Sets of Bunk Beds with Twin Bed over Full BedbrLagoon Style Heated Pool w/ sundeck & SpabrIn Pool UmbrellasbrPool Deck Lounge ChairsbrPoolside Covered Lounge with Patio Furniture, TV & Ping Pong TablebrGas BBQ GrillbrTiki Hut with Basketball Nets, ring toss, and foosballbrPutting Green & Cornhole GamebrOutdoor Deck with Patio Dining for 6brProfessional Linen Service, Complimentary WIFI, Washer & DryerbrBeach Towels, Beach Chairs, Beach Wagon & Beach UmbrellabrParking for 4 CarsbrTrailers of any kind are not permitted unless prior approval from owners.brbrDetailsbrLocated 2 blocks to the Gulf of Mexico beaches, Tarpon House will delight you with its family fun amenities.brEach of the three King bedrooms has an en-suite bathroom. The kids will love sharing the bunk room which is complete with two sets of bunk beds with a twin bed over a full bed. This bedroom also has an attached private bathroom. Each bedroom has a TV and includes crisp linens and plush towels from our professional linen company.brbrDining options include bar seating in the kitchen, a dining room table for six and outdoor verandah patio dining for six. Grill up dinner on the gas BBQ and enjoy the island breezes while overlooking the tropical backyard. After dinner, challenge the family to a game of corn hole, ping pong or basketball in the tiki hut.brbrThe quick walk to the beach is a breeze with the provided beach wagon to haul the beach chairs, umbrella and towels. The water fun continues in your own backyard private pool and spa. Relax poolside in deck chairs and under the shade of the in pool umbrellas. The poolside lounge area features patio couches and a TV to enjoy under the cover of the home and out of the sun.brbrYour guests will stay connected with complimentary Wi-FI and enjoy all of the comforts of home, including a washer and dryer.brbrTarpon House is easy walking distance to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches.brbrBedroom 1: King with TV and Ensuite BathbrBedroom 2: King with TV and Ensuite BathbrBedroom 3: King with TV and Ensuite BathbrBedroom 4: 2 sets of Bunk Beds with Twin Beds over Full Beds and Ensuite BathbrbrPlease note - pets are not allowed in this home.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The minimum requirement for this home is no less than seven nights. The maximum occupancy is eight.brbrIMPORTANT INFORMATION: brbrWe will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrTarpon House will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking.

Tarpon House-Luxury 4/4 Home on Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$428.31

Come for the SUN, stay for the FUN!!! brFind everything that makes a fun beach getaway on Anna Maria Island memorable when you stay at North Gulf Villa Beach vacation rental home at 6311 North Beach Village. This three-bedroom townhouse-style vacation rental is just a short walk to beautiful gulf beaches.brbrNorth Beach Village is located just north of the Holmes Beach town center. After a day at the beach, hop on the free trolley on Gulf Drive, and take it into Holmes Beach for great dining and nightlife. This vacation home offers three parking spaces.brbrIn the living room, find plush seating, a flat-screen television, and the open front balcony of this gorgeous Anna Maria Island vacation rental home. Wireless internet, cable television, and local calling are provided to keep you connected during your stay. This rental does offer a washer/dryer and a BBQ grill.brbrHead over to the community pool for a swim! The pool is heated, and the patio area offers seating and restrooms.brbrROOMS AMENITIESbrbrA newly extensively remodeled and colorfully painted 3BD/2BA key west, old-world style townhouse on Holmes Beach. It's located in a quiet and peaceful residential area just a half block from the pristine Anna Maria Island beaches. North Gulf Villa is just a few steps from the main free trolley line that can take you anywhere you want to go on this beautiful 7-mile island.brbrNorth Gulf Villa has all the features one associates with modern beach life, including a well-equipped kitchen and top-of-the-line appliances.brbrWhen entering North Gulf Villa, you walk up a short flight of stairs to the main level, which includes a large open-plan living area with lots of natural light, a kitchen, and a beautiful master bedroom with a KING-size bed and en suite REMODELED bathroom. brThere are two additional Queen bedrooms and a single, plus a living room queen memory sofa bed, which is more comfortable than any existing sofa bed.brbrThis townhome is spread over 3 floors. Both 2nd and 3rd-floor bedrooms offer a queen bed. There is a sofa bed in the living room for extra accommodation. There are 2 individual decks for you to relax in and soak up the sun. The first is next to the large family room, which provides extra relaxing space. It's a large outside patio. Enjoy the Japanese-style garden and waterfall. The townhouse has a flat-screen TV and a fuss ball table for additional family entertainment. The downstairs double garage accommodates the washer/dryer, extra room for parking, and your personal gear.brbrThis Villa has everything you need to enjoy a relaxing beach vacation with careful attention to detail. The owner's wish is for their guests to leave their home feeling relaxed, refreshed, and eager to return again!brbrVRC# 19-000073brNOISE ORDINANCE AFTER 10 PM brbrBEST SELLING POINTSbr*NORTHSHORE OF ISLANDbr*NEXT DOOR TO BEACH BISTRO br*1 BLOCK FROM THE BEACH br*VIEWS FROM DECKbr*FULLY REMODELEDbrbrUPGRADESbr*Hardwood floors br*Stained concrete br*Granite countertops and extra kitchen Island.br*New Travertine tile in bathrooms and new sinks and countertops br*New Ivory Antiqued cabinetrybr*Premium fixtures br*Premium new stainless steel appliances

Northshore Villa - 3 Bedroom, 2 Bathroom Vacation Rental Across from the Beach

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$227.04

Photos Updated January 2025!brLONG-TERM DISCOUNT: Stays of 4-weeks (28 nights) or more enjoy a 25% discount on the nightly rate!br(This discount is applied automatically when 28 nights or more are selected. No need to contact the office!)brbrWelcome to the Lazy Lizard located in Holmes Beach on Anna Maria Island! This newly renovated and beautifully decorated cottage is only a 4-minute bike ride to the white sand and gorgeous blue waters of the Gulf.brbrThe Lazy Lizard is a ground floor home with 2 bedrooms (one with a queen and one with two twins), a full-size pull-out sofa, and a screened-in lanai with private access off the Master bedroom (perfect for your morning coffee, quiet dinners, or an evening cocktail). The cottage is newly renovated with a brand-new kitchen, quartz counters, stainless steel appliances, and new tile flooring throughout. The tranquil coastal décor provides a relaxing space for the whole family. Beach chairs, wagons, umbrella, toys, and games are available for your use.brbrThe best part The location! Not only are we only a 4-minute bike ride/10 minute walk to Gulf beach access but we are just steps away from the local tennis courts, playground, shuffleboard, basketball court, skate park, library, soccer field, and the 63rd bay side boat ramp (GREAT for fishing or launching kayaks!). Did we mention the bait shop is within walking distance too brbrThere’s so much to do!brbrTired after a long day of hanging out at the beach Rest and relax on the covered screen-in lanai while grilling up some local seafood on the gas grill in the backyard!brbrThere is free WIFI and a Smart TVs in both the living room and Master bedroom with free Spectrum TV for live television and the ability to stream from your personal accounts. As a bonus, the nightstands come equipped with charging stations for your cell phones.brbrWe provide a professional linen service which guarantees that all of our guests will have clean and high quality sheets, bath towels, kitchen towels, and beach towels with every stay. There is also a laundry room with washer and dryer off the hallway.brbrWant to explore the island but don’t feel like driving There are several restaurants and shops within walking distance. Additionally, the FREE island trolley has a stop right around the corner and will take you all the way up to the City Pier or all the way down to Coquina beach. brbrCome check out our little slice of paradise. We’d love to host you! brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbr**Please note: This property is NOT pet friendly. NO PETS under any circumstances. Bringing a pet into our home will result in immediate eviction with no refund. brbrNote: The cottage is located on a quiet street where locals reside. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrVRC21-000146

Lazy Lizard! A Newly Renovated Island Cottage, Close to the Beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$660.15

My Grand Floridian by Anna Maria Life Vacation Rentalsbr207 N Harbor Dr, Holmes Beach, FL, 3427brbrWhat You'll Love About This Home:brLocation! 2.5 Blocks to the Beach! On a Canal!br5 Bedrooms / 5 Bathroomsbr4 Kings, Full over Full BunkbedbrPrivate Heated Pool with In-Pool Table & SeatingbrPool Loungers & UmbrellasbrOutdoor ShowerbrCovered Poolside Lounge Area with Dining Table for 8brGas GrillbrPrivate Dock on Canal, Ladder for Kayak LaunchingbrFish TablebrPutting GreenbrGame Room, Ping PongbrMultiple Verandahs & Private Rooftop DeckbrKeurig & Drip Coffee MakersbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Chairs, WagonbrParking for 5 Cars (4 in driveway, 1 in garage)brbrDetails:brMy Grand Floridian is a canal front vacation oasis packed with outdoor activities, games and fun for the entire family. The sparkling clear waters of the Gulf of Mexico and the sugar sand beach are a quick walk from the front door.brbrThe bright kitchen overlooks a dining room with seating for eight and additional stools at the island. The living area is a comfortable spot for the family to gather and enjoy the pool view from the patio doors.brbrThe main living level also features two of the king bedrooms, both with ensuite bathrooms and balcony access. The third floor includes a king bedroom and a bedroom with a full over full bunkbed connected by a Jack n Jill bathroom. The master suite on this level features a king bed, ensuite bathroom and a spiral staircase to the private rooftop deck. Guests will love the sunset views! Each bedroom includes a TV and crisp linens and plush towels in the bathrooms from our professional linen service. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrThe private heated pool features an in-pool table and seating. Relax in a pool lounger or Adirondack chair while enjoying the island breezes. An outdoor shower allows you to rinse the sand from your suit before entering the pool.brbrThe covered poolside lounge area hosts a dining table for eight for guests to enjoy a meal from the grill. The lounge furniture provides additional relaxation space. Guests will love the putting green and game room with ping pong and foosball tables.brbrThe fisherman in the family will love the dock and fish cleaning table. A ladder is available to access the canal for kayak or paddleboard launching.brbrMy Grand Floridian is easy walking distance to the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1 - King Bed, Ensuite Bathroom, Private Balcony, TV - Floor 3brBedroom 2 - King Bed, Ensuite Bathroom, Balcony, TV - Floor 2brBedroom 3 - King Bed, Ensuite Bathroom, Balcony, TV - Floor 2brBedroom 4 - King Bed, Jack n Jill Bathroom, TV - Floor 3brBedroom 5 - Full over Full Bunkbed, Jack n Jill Bathroom, TV - Floor 3brbrPlease note:brAmenities are subject to change.brThis home is not pet friendly.brThe right-side garage is not available for guest use.brThese premises are monitored by video surveillance in select exterior areas.brParking for a maximum of 5 cars. Four spaces in driveway, and one space in the east garage. Parking for additional vehicles is not available.brbrDISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. The minimum requirement for this home is no less than seven nights. The maximum occupancy is ten.brbrVRC16-000133 brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

My Grand Floridian: Canal Front, Dock, Pool, Games by Anna Maria Life Vacation Rentals

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$309.09

Welcome to Heliconia House! This remodeled and furnished two bedroom and two bathroom duplex has its own private pool. A short stroll to the Holmes Beach shopping and restaurant area, tennis courts, boat ramp, pickleball courts and dog park just around the corner. Guests will enjoy a well-equipped kitchen perfect for preparing a gourmet meal or cook outdoors on the gas grill. The living area is spacious, with plenty of seating for family and friends to take in a movie on the flat panel HDTV. Gather around the breakfast bar to enjoy your meals. The master bedroom has a King size bed and flat screen TV and ensuite bathroom with walk-in shower. The guest room has 2 full size beds, a flat screen TV and ensuite bathroom with shower/tub. Washer and dryer are available in the property. Heliconia House accommodates up to six people.brbrHIGHLIGHTSbrbr940 sq. ft. brbrPrivate pool (14x15ft, 3ft to 5ft deep) - pool heater available soonbrbrShaded outdoor sitting areabrbr300 ft. from bay access brbr0.5 miles from beach accessbrbrPack N Play and Booster SeatbrbrWork SpacebrbrBEDROOMSbrbrSleeps 6brbrPrimary Bedroom: KingbrbrSecond Bedroom: 2 Full brbrBATHROOMSbrbrPrimary Bathroom: Walk-in ShowerbrbrSecond Bathroom: Shower/tubbrbrEXTERIORbrbrRelax in the pool after a day at the beach. Enjoy outdoor living under a covered patio area and use the gas grill to fire up a great dinner.brbrAlso enjoy the common park area behind Heliconia House there is access through the gate at the rear of the pool.brbrHeliconia House is a pet friendly property for dogs up to 25 lbs. The non-refundable pet fee is $150.00 per pet per stay.The pet fee does not cover any damage caused by the pet. brbrThe Holmes Beach Dog Park is just a very short walk away.brbrBeach items - chairs, cart and umbrella.brbrThere are two parking spaces reserved for the guests of this property. brbrPool heater coming soon.brbrOptional pool heat, up to 86 F, is available from November to April at $150/week. Weather conditions may affect the temperature of the pool. Pool alarms are mandated per city licensing ordinance and cannot be disarmed. Pools are professionally serviced weekly and debris due to tropical climate might occur in between service days. Duncan Real Estate will expedite repairs of reported malfunctions, but no refund will be made for circumstances beyond our control. brbrPlease keep in mind that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. brbrVRC-16-000319brbrAmenities Include:brbr- Bedroom 1 Kingbrbr- Bedroom 2 2 Fullbrbr- Bathroom 1 Walk-in Showerbrbr- Bathroom 2 Walk-in Showerbrbr- Hot Waterbrbr- Beach Access .5 milesbrbr- Bay Access 300 ftbrbr- Ground Level Ybrbr- Central A Cbrbr- Cental Heatbrbr- Sqft under a c 948brbr- Free Parkingbrbr- Parking Spots 2brbr- Dogs up to 25 lbs Ybrbr- Self Check Inbrbr- Keyless Entrybrbr- Bath Towelsbrbr- Beach Towelsbrbr- Quality Linensbrbr- Hair Dryerbrbr- Hangersbrbr- Refrigeratorbrbr- Ice Makerbrbr- Stovebrbr- Ovenbrbr- Cookwarebrbr- Toasterbrbr- Blenderbrbr- Keurigbrbr- Drip Coffee makerbrbr- Dishwasherbrbr- Microwavebrbr- Breakfast Barbrbr- High Chairbrbr- High Speed WIFIbrbr- TV 3brbr- TV Streaming Onlybrbr- Washerbrbr- Dryerbrbr- Ironbrbr- Ironing Boardbrbr- Cleaning Kitbrbr- First Aid Kitbrbr- Fire Extinguisherbrbr- Smoke Alarmbrbr- Carbon Monoxide Alarmbrbr- Private Pool Ybrbr- Pool Dimensions 14ft x 15ftbrbr- Pool Alarmsbrbr- Patiobrbr- Foot Showerbrbr- Propane Grillbrbr- Beach Amenitiesbrbr- Tennis Courtsbrbr- Pickleball Courtsbrbr- Mold Free Certificatebrbr- Duncan Emerald Clubbrbr

Heliconia House by Duncan Real Estate

Holmes Beach, Florida, United States

1

Bath

Sleeps

Exceptional(5)

$366.73

Welcome to Lucky Me Too on Anna Maria Island! Location, Location, Location! Directly across from Anna Maria Island Beach Cafe! brbr Property Highlights:br✨ 2 full bedrooms with king bedsbr✨ 2.5 bathsbr✨ Washer & dryer in unitbr✨ Beach essentials includedbr✨ One-minute walk to the beachbr✨ Heated community poolbr✨ Plenty of space for 6br✨ Screened-in balcony with room to dinebr✨ Fully equipped kitchenbrbrLucky Me Too is located in Holmes Beach on Anna Maria Island. Situated in an ideal location right across from Anna Maria Island Public Beach! This newly updated, two bedroom, two and a half bath townhome is a one minute walk to beaches and steps away from the free island trolley. The screened lanai overlooks the heated pool that is shared with a small number of units. An added bonus there is undercover parking that accommodates two cars and the townhome sleeps up to six guests. This townhome has a master bedroom with a King bed, plus the guest room also has a King. The property has beach chairs, beach umbrellas, beach wagon, and beach towels for guest use. brbrLucky Me Too is conveniently located near the main shopping areas. The townhome is walking distance to Publix supermarket, a drug store, shopping stores and restaurants. Across the street you'll find the Anna Maria Island Beach Cafe, offering their famous pancake breakfast, live music and expansive white beaches. Walk the powdery sandy beach for miles in either direction and enjoy the amazing Gulf Coast warm waters and spectacular sunsets. brbrBike, drive or take the trolley to the shops and restaurants in the City of Anna Maria just to the north. Quaint Bridge Street and its pier are just a little further to the south. Holmes Beach offers a choice of sixteen restaurants, unique coastal shops, boating and fishing charters, and a marina. brbr This townhome participates in a professional linen program so that you can rest well in luxury. brbrPayment and Cancellation Terms brbrAt the time of booking your credit card will be charged by Shore Thing Property Services LLC for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrWe require an initial 25% deposit with final payment due 60 days prior to your arrival date. Full payment will be due immediately if the arrival date is within 60 days. brbrAlthough the VRBO policy states no refunds, we will refund in the event you need to cancel your reservation prior to 60 days before your arrival date. We will implement our Shore Thing cancellation policy as indicated on the rental agreement. This allows for a refund of the deposit paid minus $250 cancellation fee and the original management fee. Within 60 days of arrival there are no refunds. brbrAdditional Information brbr We generally require a minimum night stay of 7 nights with Saturday check-in during high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you! brbrHousekeeping will provide a starter supply of toilet paper, paper towel, soap, and garbage bags but guests will likely need to replenish the supply during their stay. brbrAnna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10pm and 8am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors. brbrVRC22-000193

Lucky Me Too! 2BD 2 Bath Across from AMI Beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$1001.36

Heavenly Haverkos 211 Haverkos, Holmes Beach, 34217 VRC21-000169 What you will love about this property: • Bayfront with private dock • Less than a 10-minute walk to the beach • Large pool within ground spa • Game room, large outdoor bar and entertainment • Private balcony with views • Full gourmet kitchen • Beach chairs, beach wagon, corn hole, ping pong and foosball • Monthly rental (28 nights) and quiet cul-de-sac road • Professional Linen program • Full size washer and dryer • Close to shops, restaurants and free trolley access • In the heart of Holmes Beach Property details: Welcome to Heavenly Haverkos! This luxury home is the ultimate vacation spot, featuring a private dock for boats up to 42 feet, a bay-facing pool, and an in-ground spa. With five bedrooms, five full baths, and two half-baths, it's perfect for families and large groups. Entertainment options abound with foosball, ping pong, and two outdoor bars for dining and drinking al fresco in paradise. Nestled amidst lush palms and tropical greenery, Heavenly Haverkos offers ample parking including space for a boat trailer, while the elevator simplifies grocery and luggage transport. The ground floor invites relaxation with games, chic seating, and a convenient half bath. Upstairs, the great room showcases bay vistas, a state-of-the-art kitchen boasting Wolf and Subzero appliances, a capacious island with breakfast bar, and a cozy dining nook. Sink into ultra-plush sofa seating, unwind with a movie on the flat panel TV, or cozy up by the electric fireplace on chilly Florida evenings. Wake up rejuvenated in any of the five luxury-designed bedrooms with impeccable decor, premium bedding, and endless water views. The primary suite indulges with a king bed and a sleek ensuite bathroom featuring a large vanity with dual sinks, a walk-in shower with multiple shower heads, and a soothing soaking tub. The other bedrooms provide a range of sleeping arrangements, each accompanied by scenic views and ensuite bathrooms. Convenience is prioritized with two laundry rooms, ensuring ease on each level. From sunrise to golden sunsets, bask in the serenity of your outdoor oasis. Lounge on a cozy lounger with a captivating book or indulge in some leisurely fishing from the dock, complete with a convenient cleaning station for your catch before grilling on the gas grill. Mix up a refreshing cocktail at the outdoor bar and plunge into the pool to rejuvenate your senses after a blissful day at the beach which is just a quick walk away. We cannot wait to have you as our guests at Heavenly Haverkos! Get everyone together in comfort and style at Heavenly Haverkos. Book with us today. Bedrooms & Bathrooms • Primary Bedroom, 2nd floor: King bed, walk-in closet, and ensuite bathroom with double vanity and enclosed shower with soaking tub • Second Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower • Third Bedroom, 2nd floor: Queen bed and ensuite bathroom with walk-in shower • Fourth Bedroom, 2nd floor: Full bed and ensuite bathroom with walk-in shower • Fifth Bedroom, 2nd floor: Two full over full bunk beds and ensuite bathroom with walk-in shower This property participates in our Professional Linen Program. In Beach House Real Estate's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, wash cloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. Exciting news Golf carts offer a delightful, cost-effective, and hassle-free means of transportation on Anna Maria Island throughout your visit. Live life at a slower pace while on vacation. Cruise around in the Florida sunshine feeling the Gulf Coast breeze. Rent a six-seater electric golf cart at only $750 a week. Please contact us to reserve your golf cart today! Are you bringing the kiddos We have pack & plays and highchairs too! Your item(s) will be at your rental property for your arrival, and we will pick them up at your departure. We rent by the week: Pack & Play - $50.00 Highchair - $40.00 Please contact us to reserve your baby equipment. Friendly reminders Required 28-Night Minimum Stay. Boat Slip-Accommodates up to 42-foot Vessel. Boat Lift is not for guest use. There are No pets allowed in this home. This home is managed by Beach House Real Estate, an Anna Maria Island property management company. This property has an active Ring doorbell and additional video surveillance on the pool equipment only. Please note that there is no elevator for this property. Please remember you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without a refund. We do not accept reservations from anyone under 25 years of age. We do not allow people under 25 to occupy a property unless accompanied by someone over 25 years of age. Please note: 6 cars at maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

Heavenly Haverkos- Luxury 5 bedroom, Bayfront with private docks, pool and spa!!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$452.78

Livin of Sunshine is your perfect island escape! This brand-new, beautifully remodeled three-bedroom home offers the ideal blend of comfort, style, and fun. Just minutes from the beach and within walking distance to the Holmes Beach Shopping Center, you’ll have easy access to restaurants, boutiques, and local favorites.brbrEnjoy your private heated pool, challenge family and friends to on-site putt-putt golf or cornhole, and relax in the modern, thoughtfully designed living spaces. After a sun-soaked day at the beach, unwind poolside or take an evening stroll to nearby shops and dining. Whether you’re here to relax or explore, Livin of Sunshine sets the stage for an unforgettable island getaway. brbrThe completely remodeled mid-century gem has 3 bedrooms and 2 bathrooms an alll in one cooking, dining and living space. The kitchen is well appointed so if you want to create a home cooked meal you can. The bedrooms have spacious closets and dressers so you can enjoy a long term stay. The outdoor space is the where the real heart of this home lies. The pool is big enough to get your laps in or just relax on a raft. You also have the 6 hole putting green where you can practice your shots and the Tiki hut gives a tropical shelter that will keep you cool during sunny days. There is a large enough drive way to accommodate 4 cars and space for a golf cart. brbrHolmes Beach VRC25-000068

Livin' on Sunshine! ....Pool, Putting Green, Corn Hole & Tiki Hut

Holmes Beach, Florida, United States

3

Bed

Bath

Sleeps

$904.32

Welcome to Vela Mar!brOn Anna Maria Island (Holmes Beach, FL)brbrThe SpacebrVela Mar is where elevated coastal living meets modern luxury innovation. Designed with intention and inspired by the sophistication of Miami-style smart living, this fully integrated luxury residence blends architecture, technology, comfort, and island atmosphere into one immersive experience.brbrFrom the moment you arrive, the home feels sleek yet welcoming — where ambient lighting, travertine flooring, refined textures, and seamless indoor-outdoor living create a stay that feels both indulgent and effortless. Every detail has been thoughtfully curated to elevate the guest experience, from integrated smart-home systems to custom built-ins and resort-inspired amenities.brbrDesigned for guests who appreciate modern convenience without sacrificing warmth or comfort, Vela Mar offers a boutique luxury atmosphere unlike anything else on Anna Maria Island.brbrPerfect for: Families, couples, extended stays, luxury travelers, workcations, or guests seeking a modern coastal retreat with elevated comfort and smart-home convenience.brbrHighlightsbr- Fully integrated luxury smart homebr- 4 bedrooms / 3 bathroomsbr- Pet-friendly with prior approval (see policies)br- Resort-style private poolbr- Alexa voice-controlled smart home featuresbr- Lutron dimmable lighting throughoutbr- Pentair smart pool + heater controlsbr- Tesla EV chargerbr- Bose 700 Wi-Fi soundbarbr- 85-inch smart TV in living roombr- Smart TVs in main bedroomsbr- Travertine flooring throughoutbr- Custom built-in beds with reading lights + USB chargingbr- Samsung Bespoke refrigeratorbr- Built-in oven + microwave towerbr- Ninja coffee station + premium kitchen appliancesbr- Smart locks + Ring security systembr- Smart LG washer + dryerbr- Parking for up to 4 vehiclesbr- Impact windows + doorsbr- Metal roof constructionbr- Short drive to Holmes Beach restaurants, boutiques, and Gulf beaches.brbrInterior Spacesbr- Living Area: Expansive open-concept living space featuring an 85-inch smart TV, Bose 700 soundbar, reclining leather seating, ambient lighting, and seamless flow into the kitchen and dining areas. Designed for both entertaining and relaxed coastal living.br- Dining Area: Spacious dining and gathering space ideal for shared dinners, morning coffee, or evenings spent reconnecting after beach days.brbrBedroomsbr- Primary Suite: Custom built-in bed, reading lights, USB charging ports, smart TV, and refined modern finishes designed for elevated comfort.br- Guest Bedrooms: Additional thoughtfully designed guest rooms featuring custom built-ins, smart technology, and modern conveniences throughout.br- Bathrooms: Spa-inspired bathrooms with LED mirrors, hand showers, bidet sprayers, built-in soap dispensers, and sleek luxury finishes.brbrOutdoor LivingbrStep outside into your private coastal retreat — where modern design meets effortless island relaxation.br- Pool Area: Private resort-style pool with integrated smart controls for heating and lightingbr- Outdoor Living: Lounge and gathering areas designed for both daytime relaxation and elevated evening ambiancebr- Exterior Features: Smart exterior access, modern landscaping, and parking for up to 4 vehiclesbrbrKitchen & Diningbr- Gourmet kitchen with premium Samsung SmartThings appliancesbr- Samsung Bespoke refrigeratorbr- Built-in oven + microwave towerbr-Dual Keurig + ground coffee Ninja brewerbr- Ninja coffee makerbr- Ninja blender + Ninja air fryerbr- Instant Potbr- Cuisinart 4-slice toasterbr- Fully stocked cookware, dinnerware, and serving piecesbrbrA kitchen designed for effortless entertaining, elevated mornings, and memorable evenings in.brbrSmart Home Featuresbr- Alexa voice controlbr- Whole-home high-speed Wi-Fibr- Lutron dimmable lightingbr- Honeywell T6 Pro smart thermostatbr- Pentair ScreenLogic2 pool automationbr- Smart locks on entry + exterior bathroombr- Samsung SmartThings appliance integrationbrbrAdditional Amenitiesbr- Smart LG washer + dryerbr- Titanium iron + titanium hair dryerbr- High-suction vacuumbr- Beach towels + premium linensbr- Charcoal grillbr- Beach gear rental credit included (chairs, umbrellas, bikes, and more)brbrParkingbr- Expansive parking accommodations for up to 4 vehiclesbr- Space for guests traveling with multiple vehicles, golf carts, boat trailers, or additional recreational equipmentbr- RV parking may be considered with prior notice and approvalbr- Tesla EV charging stationbrbrAt Vela Mar, every detail was designed to create a stay that feels elevated, connected, and unforgettable — where modern luxury and island living exist in perfect harmony.brbrPoliciesbrbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNO SMOKING.brbrPets are welcome with prior approval, provided they meet our pet policy guidelines. We allow a maximum of two pets, each weighing under 65 lbs. A pet fee applies based on the length of your stay: $100 for stays under 4 days, $200 for stays of 4-14 days, and $400 for stays of 15+ days, per pet.brbrBooking & Fee PolicybrInclude all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.brbrOptional Services (subject to approval)brEarly check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.brbrReservations & Guest RequirementsbrMost stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.brbrQuiet Hoursbr10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.brbrCleaning & LinensbrHome is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.brbrGolf Cart RentalsbrExplore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.brbrPool & SpabrPool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.brbrProperty SecuritybrExterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.brbrPayments & Cancellation PolicybrPolicies updated October 6, 2025 — see full Terms & Conditions for details.brbrPayment SchedulebrDepositbr- Reservations up to 20 days: 50% of total amount due at time of booking.brRemaining Balancebr- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.brbrCancellation PolicybrFor Reservations of 20 Days or Lessbr- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.br- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.br- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.br- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.brbrTravel InsurancebrCSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.brbrAdditional TermsbrNo refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.brbrHolmes Beach Vacation Rental License: VRC26-000045brMax Occupancy: 8 Guests | Max Vehicles: 4brInformation deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Vela Mar - Modern Luxury Pool Retreat on Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$871.01

We have found our perfect spot on the beach. After visited the resorts and beaches of Florida for many years we are here to stay: at Anna Maria Island. Unfortunately only for holidays - the rest of the time you can take advantage of it as a tenant. Three comfortable bedrooms, the master with a king-size bed and sea views, a queen in the second and the third with two queen beds. The two bathrooms have walk-in showers. Sliding doors in the living room and the kitchen take you directly to the deck and there you sit or lie virtually on the beach. Just down the stairs and into the clean and warm waters of the Gulf of Mexico. Almost every day you have the chance to discover dolphins. In only 500 meters you will find at Publix everything you need. Never forget the sunset with a drink on the terrace. Then you decide whether you want stay home for a steak on the Weber grill or dine out at the City Pier or one of the many other restaurants. In May 2011, we have renovated the house completely.

Comfortable vacation home directly on the beach and sunsets from the terrace

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$217.53

Anna Maria Island is a stunning destination in Florida, known for its serene atmosphere and easy accessibility. The island boasts breathtaking sunsets, gentle breezes from the Gulf of Mexico, and miles of pristine white sand beaches. This private and tranquil home, situated on the ground floor of a two-unit building, features two bedrooms with king-size beds, a full bath with tub and shower plus an additional half bath, a fully equipped kitchen, and a private screened in lanai. Recently renovated in the summer of 2025, it offers bright, airy spaces with fresh paint, and all-new furniture. Guests can unwind in the yard or on the lanai and enjoy evening strolls to the beach for sunset views. This is 1/2 of a duplex, the second unit is an apartment above the garage it is not on top of this unit. The adorable cottage-style duplex is within walking distance of the Gulf's beautiful beaches, village shops, restaurants, cafes, and a library. For added convenience, a free island trolley is available, and both Sarasota International Airport and Tampa International Airport are just 40 and 70 minutes away, respectively.

Terrific 2-bedroom house in Holmes Beach

Holmes Beach, Florida, United States

Bed

1

Bath

4

Sleeps

$306.27

Watch the world go by on AMI as you enjoy the sea breeze on your private front deck. Unwind in the hot tub after a day at the beach and be sure to catch the sunset over the gulf, there's nothing better than reflecting on your day as the sun eases below the horizon.brbrThis is a lovely split level home. Enter the home at the front deck with outdoor dining area, grill, and additional seating. Through the front door, step into the main open plan living area of the house. This space has two couches (one can be converted into a queen sized sleeper), a recliner, and large tv. It flows into the dining area with full sized dining table plus window seat as well as fully equipped kitchen. Bedrooms are a half story up from the main living area providing separation for the early birds and those who want to sleep in while on vacation.brbrUpstairs are two bedrooms, each with a king sized bed and tvs with Roku streaming devices. In the hallway between the two bedrooms is the primary full bathroom with tub and shower. Across the hall from the bathroom is the fully stocked linen closet with bath towels, beach towels, and select toiletries.brbrTake the short half-flight of steps down and you'll find a second living area, with a queen daybed and tv as well as bistro set. The downstairs living area opens with sliding glass windows out to the front of the house with a pair of bikes available as well as a storage chest full of beach chairs and life jackets to use with the paddle boards and kayaks under the patio. The downstairs living room connects to the second bathroom with shower at the back of the house as well as the washer and dryer. Through this bathroom is access to the back yard.brbrThe back yard has a bromine hot tub as well as additional seating and a pair of lounge chairs to enjoy the rear deck area. Relax in this tranquil space surrounded by the lush green palms.brbrThere is a games cabinet on the lower level of the home with assorted board games and puzzles as well as an assortment of toddler toys.brbrThis house is very child friendly but not baby proof. We have lots of amenities for babies/toddlers, but there are stairs and no baby gates. The baby items can be set up for you ahead of time, just message me, otherwise most of the baby gear is in the closet of the front bedroom so as to be out of the way for those without young children.brbrWe generally require a stay of 7 nights with Saturday check-in during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you!brbrOur cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels.

Destination Relaxation

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$508.12

Experience the serenity of our newly renovated, single-story sanctuary, nestled perfectly alongside an idyllic canal. This comfortable retreat, set in a tranquil area of AMI paradise, boasts a large private pool and a spacious floorplan to ensure utmost relaxation and rejuvenation. Enjoy three voluminous bedrooms, each complemented with a private, modern ensuite bathroom, offering plenty of space to unwind in style. Unleash your culinary creativity in the modern kitchen, bond in the cozy family room, or host a memorable dinner in the spacious dining area that effortlessly seats six. brbrFor the adventurous at heart, enjoy the option to dock your boat right in your backyard, an ideal base for exploring the mesmerizing beauty of Anna Maria Island`s waters. With the comfort of two king-sized and two queen-sized beds, our home is capable of pampering up to six guests, making it the perfect destination for a blissful family escape or an exciting rendezvous with friends. brbrPartake in the delicious local culinary scene, explore charming boutique shops, and soak up the breathtakingly beautiful white sand beaches and crystalline turquoise gulf waters that our location is celebrated for. Your unforgettable Anna Maria Island adventure awaits – secure your dream vacation today!brNo smoking of any kind, no pets, no parties or events allowed. Guest will be responsible for any and all damages to the property that they or their guests may incur. A signed Rental Agreement is required with your reservation. A complete list of House Rules will be available at the Rental Property.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrMaximum Guests Allowed - 6brMaximum Parking - 5 VehiclesbrMinimum Stay - 28 DaysbrProperty License # - VRC25-00075

New Listing Discount! Beautifully renovated home w/pool on canal near beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$504.98

Whether you're here for long beach days, sunset strolls, or cruising the island, Groovy Guava makes island life feel effortless.brbr*Features Include* brbr* Private heated pool br* Pool loungers br* Private back patio with outdoor dining br* Propane grill br* Washer and dryer br* 2 bedrooms, 2 full bathrooms br* Ground floor and easily accessible br* 1/2 block to the beach! br* Complimentary 6-seat street legal golf cart for stays through November 28, 2026br* Beach chairs, umbrella and cart brbrSpecial Notice: Complimentary 6-seat street legal golf cart included with all stays through November 28, 2026! Cruise to the beach, restaurants, and island shops with ease while this exclusive perk is still available.brbrWelcome to Groovy Guava, a bright and cheerful island retreat just half a block from the powder-white beaches of Anna Maria Island. This charming two-bedroom half-duplex offers the perfect mix of laid-back beach living and private outdoor space, complete with your own heated pool. brbrInside, Groovy Guava feels welcoming and comfortable with an open living space and a fully equipped kitchen that makes vacation dining easy. Enjoy casual breakfasts before heading to the beach or gather around the dining table after a day of island adventures.brbrWhen you're ready to explore, you are within easy walking distance to some of the island’s favorite spots including The Feast, Freckled Fin, Island Creamery, Hurricane Hanks, and more.brbrStep outside and you’ll discover your own private tropical escape. The fenced backyard is surrounded by lush landscaping and features a sparkling heated pool, perfect for cooling off after a day at the beach. Fire up the grill and enjoy alfresco dining on the patio before heading out to catch one of Anna Maria Island’s famous sunsets.brbrAt the end of the day, retreat to the comfortable primary bedroom featuring a king bed and a private ensuite bathroom with walk-in shower. The guest bedroom offers a queen bed and a Twin XL bed, making it perfect for additional guests or kids. A second full bathroom with tub is located just off the hallway.brbrWith its unbeatable location, private pool, and fun island touches, Groovy Guava is the perfect home base for a relaxed and memorable Anna Maria Island getaway.brbrIf you need space for a larger group of friends or family we are happy to also offer Beach Daze, the other side of this duplex, right next door! brbrPET POLICY:brbrWe are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing.brbr1 pet maximum unless granted an exception. Weight limit of 75 lbs maximum per pet.brbrDue to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted:brbrPit Bull, Akita, Rottweiler, German Shepherd, Siberian Husky, Malamute, Doberman Pinscher, Chows, Any Wolf-dog hybrid, Any other dog that has been known to have bitten anyonebrbrADDITIONAL INFORMATION brbrWe generally require a minimum stay of 7 nights with Saturday check-in during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you! brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay. brbrAnna Maria island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors. brbrVRC16-000148 brbr This home provides off-street parking for up to 2 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

Groovy Guava by Beach Boutique Rentals

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$479.88

Whether you're spending your days at the beach or relaxing poolside in your private backyard oasis, Beach Daze makes it easy to settle into vacation mode the moment you arrive.brbr*Features Include* brbr* Private heated pool br* Pool loungers br* Beach chairs, umbrella and cart br* Private back patio with outdoor dining br* Propane grill br* Washer and dryer br* 2 bedrooms, 2 full bathrooms br* Ground floor and easily accessible br* Complimentary 6-seat street legal golf cart for stays through November 28, 2026br* Beach chairs, umbrella and cartbrbrSpecial Notice: Complimentary 6-seat street legal golf cart included with all stays through November 28, 2026! Cruise to the beach, restaurants, and island shops with ease while this exclusive perk is still available.brbrWelcome to Beach Daze, a bright and breezy island retreat just half a block from the powder-white beaches of Anna Maria Island. This charming two-bedroom half-duplex offers the perfect blend of comfort, convenience, and laid-back coastal living, complete with a private heated pool.brbrInside, Beach Daze feels welcoming and comfortable with an open living space and a fully equipped kitchen with eat-in dining area that makes vacation meals simple and stress-free. Enjoy casual breakfasts before heading to the beach or gather around the table after a day of island adventures.brbrWhen you are ready to explore, you will be within easy walking distance to some of Anna Maria Island’s favorite dining spots including The Feast, Freckled Fin, Island Creamery, Hurricane Hanks, and more.brbrStep outside and you will discover your own private tropical retreat. The fenced backyard is surrounded by lush landscaping and features a sparkling heated pool, perfect for cooling off after a sunny day on the sand. Fire up the grill and enjoy alfresco dining on the patio before a quick walk to the beach to catch one of Anna Maria Island’s legendary sunsets.brbrAt the end of the day, retreat to the comfortable primary bedroom featuring a king bed and a private ensuite bathroom with walk-in shower. The guest bedroom offers another king bed, creating a perfect setup for couples or small families traveling together. A second full bathroom with tub is conveniently located just off the hallway.brbrWith its unbeatable location, private pool, and easy island charm, Beach Daze is the perfect home base for a relaxed and memorable Anna Maria Island getaway.brbrIf you need space for a larger group of friends or family we are happy to also offer Groovy Guava, the other side of this duplex, right next door! brbrPET POLICY:brbrWe are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing.brbr1 pet maximum unless granted an exception. Weight limit of 75 lbs maximum per pet.brbrDue to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted:brbrPit Bull, Akita, Rottweiler, German Shepherd, Siberian Husky, Malamute, Doberman Pinscher, Chows, Any Wolf-dog hybrid, Any other dog that has been known to have bitten anyonebrbrADDITIONAL INFORMATION brbrWe generally require a minimum stay of 7 nights with Saturday check-in during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you! brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay. brbrAnna Maria island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors.brbrVRC16-000176br brThis home provides off-street parking for up to 2 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

Beach Daze by Beach Boutique Rentals

Holmes Beach, Florida, United States

Bed

Bath

4

Sleeps

$330.64

Steps to Holmes Beach! 3BR 2BA Beach Bungalow – Walk to Beach with Beach GearbrbrWelcome to your relaxing beach bungalow steps from the light sand and Caribbean-like water on Anna Maria Island. If you’re seeking a true “island vibe” experience, Island Soul Life is the bungalow that will call to your soul.brbrThis location is sought after because of its direct access to a more private section of the beach ushering you into the island vibe where getting your toes in the sand is simple, healing, and grounding.brbrThe spacebrIsland Soul Life Beach Bungalow provides you the peaceful atmosphere to enjoy unforgettable beach days filled with laughter, beautiful memories, and soaking in the best of what nature and Anna Maria Island freely gives.brbrEverything you need for the perfect beach vacation is at Island Soul Life Beach Bungalow, including beach gear and a fully stocked home.brbrThe LOCATION embodies the heart of Anna Maria Island and all it has to offer:br• Beach access across the street – 100 feetbr• Walking distance to the free island trolley stops – 0.2 milebr• Close to Bridge Street’s shops, restaurants, nightlife, and bayfront living – 1.7 milesbr• Close to Anna Maria shops, restaurants, beachside yoga, and more – 3.7 milesbr• A morning stroll leads to close cafes – 0.4 milebr• Publix grocery store – 0.7 milebrbrRequirements (City of Holmes Beach Land Development Code):br• 7-day minimum staybr• Occupancy: 6 personsbrbrThe Space:br3 Bedrooms / 2 Bathrooms – ideal for families, small groups, couples or individualsbr• Primary Bedroom: King bed + en-suite bathbr• Guest Bedroom 1: Queen with smart TVbr• Guest Bedroom 2: Twin trundle bed and deskbr• Extra self-inflating twin air bedbr• Bright, open living space with smart TVbr• Fully stocked kitchenbr• Dining area for shared meals and game nightbr• Designated work spacebr• Washer/Dryer conveniently located in the hallwaybr• Wifi + Smart TVs for streaming and remote workbr• Outdoor, screened deck with dining table & chairsbr• Outdoor showerbr• Parking for 3 vehiclesbr• Professionally cleaned and sanitizedbrbrBeach Gear Included: beach chairs, towels, wagons, umbrellas, small coolerbrbrExtras: Dream On Me travel playard, games, and booksbrbrOutdoor Living:br• Screened outdoor deck with dining table & chairsbr• Outdoor seatingbr• Grill (charcoal and propane)brbrLicense # VRC24-000056brbr“You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property” (Chapter 4-14, City of Holmes Beach Municipal Code).brbrPet Fee with Approval: $150 taxable pet fee, if pet is approved.brbrProximity to popular destinations:br• Beach Access – 100 feetbr• Free Trolley Stops (2) – 0.2 milesbr• Anna Maria - Pine St – 3.7 milesbr• Bridge St - Bradenton Beach – 1.7 milesbr• Sarasota Airport (SRQ) – 15 milesbr• Tampa Airport (TPA) – 53 milesbr• Busch Gardens – 61 milesbr• Disney World – 93 milesbr• Universal Studios and SeaWorld – 118 milesbrbrGuest accessbrGuests have access to the full house and surrounding yard space (not fully fenced).brbrOther things to notebrFront door code provided for easy check-in and check-out.

Steps to Beach - Prime Location Beach Bungalow – Beach Gear

Holmes Beach, Florida, United States

3

Bed

Bath