Vacation Rentals By Owner In Holmes Beach, FL

VRC19-000271-0*br“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. ”This city enforces a NOISE ORDINANCE with quiet hours from 10:00 PM to 7:00 AM, during which noise levels must not exceed 50 dBA. Daytime limits (7:00 AM to 10:00 PM) are set at 65 dBA. The ordinance prohibits loud, unreasonable noise, including amplified sound, audible beyond the property boundary. brbrbrContact me for minimum requirement. VRBO website does NOT determine availability--ONLY owner does. Further Questions and/or request dates, contact me per email.brCalendar is not posted for this reason. If I am contacted during a weekend, I can't respond until the following Monday. The rental charge December $13,000(plus tax),for January $13,000 (plus tax), February is $13,000 (plus tax) March, $15,000(plus tax) & April $15,000(plus tax).. Contact me for various months of your choice if not listed here. Keep in mind--if your request includes a National Holiday, rates will be higher. (10-12% more)brbrOur home has recently had the exterior painted September 2022, all driveway pavers cleaned, and restored, and a new roof installed as of November 2021. New stainless steel appliances and shower doors July 2025.brbrFramed by tall twisted Sea-grape trees, and Saw Palmettos, you will find our 3800 square ft.' tropical green' painted beach house, stretching up to three levels. Broken pieces of white sea shells, surround the tropical landscaping and coral pavers that make up the driveway. We built our home in 1996, and have enjoyed it as a meeting place for family reunions, friends, and Holidays. This is a house that has more windows than walls, and when you see the view, you'll understand why. Recently we updated it with new replacement windows and doors, hardy-board siding , new cabinets and granite counter tops in kitchen and bathrooms. brbrThere are roll-a-way shutters (for impending Hurricane-USE only), central intercom & stereo system, security system, and an elevator in the home that stops at three levels. The LR has a beautiful keystone fire place, with high cypress wood ceilings. House is decorated with a 'beach motif' with comfortable furniture.brbrThe house is very open, tiled floors throughout, and has ceiling fans in every room. Two of the guest rooms have a queen size bed, and there is a large 'dorm' room on the back of the house with kind bed, bunk beds and trundle beds/ sleep 6 people. The room has an adjoining large bathroom with shower (2 shower heads) and Koehler tub. Cable and flat screen. The large bathroom off dorm room has accessible shower for handicapped guests.brTVs in every room, PlayStation in guest room, DVD player. High-speed Internet access. Printer & Fax. brThe covered wrap-around, screened deck area extends out behind the dining and LR areas, with a white porch swing, and new comfortable patio furniture.brLarge 2-car garage, and separate laundry room with W/D on ground level. Ping-Pong Table under lanai area, with 2 outdoor showers; one enclosed.brThe master suite itself, is over 800 square feet, surrounded by several windows overlooking the tree-tops with views of the Gulf. It makes up the top floor with a King size bed, wet-bar, keystone fireplace, home office area, sitting area with sofa, and covered deck . Adjoining is the master-bath with corner Jacuzzi, separate toilet closet with bidet, and large shower.brYou may receive a refund of up to 100% of your total rental payment if you provide written notice of cancellation at least 60 days prior to your arrival date, and paid with electronic check.br**Travel Protection Insurance, or trip cancellation coverage is extremely important and is highly advisable. Protect your booking, your flights, etc. Make sure you're dealing with a well-known brand, like Allianz Travel Insurance, Travelex, Travel Guard or Generali Global Assistance. Find the Right Travel Insurance Plan for You.

Family Friendly Anna Maria Island Vacation Home-Only 200 steps to the beach...

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$372.0

Barefoot Energy by Anna Maria Life Vacation Rentalsbr5613 Gulf Drive, Holmes Beach, FL 34217brbrWhat You'll Love About This Home:brLocation! Public Beach Access is Across the Street!br3 Bedrooms / 2 BathroomsbrKing, Queen, Twin, Twin over Twin Bunkbed, Queen Sofa SleeperbrPrivate Heated Pool & SpabrPoolside Lounge SeatingbrRooftop Deck with Seating & Gulf ViewsbrGas GrillbrPatio DiningbrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs, Beach WagonbrParking for 4 CarsbrbrDetails:brWake up to salty breezes and the sound of waves at Barefoot Energy, an inviting Anna Maria Island retreat, perfectly located directly across the street from the beach. Designed for relaxed island living, this three-bedroom, two-bath vacation home blends comfort, convenience, and unforgettable Gulf views—making it an ideal escape for families or friends.brbrInside, you'll find flexible sleeping for everyone, including a king suite, a queen bedroom, and a fun third room with a twin bed and a twin-over-twin bunk, plus a queen sofa sleeper for extra guests. Crisp comfort is guaranteed with professional linen service, and modern conveniences like complimentary WIFI and a washer and dryer make longer stays effortless.brbrStep outside to your private heated pool and spa, surrounded by poolside lounge seating for sunny afternoons and evening unwinding. Fire up the gas grill and enjoy meals at the patio dining area, or head upstairs to the rooftop deck, where seating and sweeping Gulf views set the scene for sunset cocktails and stargazing. Beach days are a breeze with provided beach towels, chairs, and a wagon, and parking for two cars keeps everything easy. From morning swims to golden sunsets, this home delivers the very best of Anna Maria Island living.brbrBarefoot Energy is easy walking distance to Gulf Ave and 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, Balcony, TV - Floor 2brBedroom 2 - Queen Bed, TV - Floor 1brBedroom 3 - Twin over Twin Bunk Bed, Twin Bed, TV - Floor 1brbrPlease note:brThis home is not pet friendly.brAmenities are subject to change.brParking is available for 4 cars. Parking for additional cars is not available.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. brVRC16-000774 brbrIMPORTANT 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.

Barefoot Energy: Across the street from Gulf! Rooftop Deck Pool & Spa by Anna Maria Life

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$216.33

VRC20-000192brbr2BR · 2BA · Sleeps 4 · 30-Night Minimum · Two Heated Pools · Tennis Court · 5-Min Walk to Manatee Beach · Condo Application Required · 2 Parking Spaces · Completely renovated in 2026brbrImportant before booking: West Bay Cove 216 requires a minimum stay of 30 nights and a condo application — contact IVP to start the process before booking.brbrA two-bedroom condo in the heart of Holmes Beach with two heated pools, a tennis court, and a 5-minute walk to Manatee Beach on the Gulf. Publix, CVS, shops, and restaurants are all within easy walking distance. The free Anna Maria Island trolley stops nearby — a car is not needed for daily island life.brbrTwo bedrooms sleep four. The primary suite has a king bed. The guest bedroom has two twin beds. Two full bathrooms. Flat-screen TVs in the living room and primary bedroom. High-speed WiFi included.brbrWest Bay Cove 216 requires a 30-night minimum stay with parking for two vehicles. Condo application required. Not pet-friendly.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

West Bay Cove 216 · Pool Views · 30-Night Min · Renovated 2026

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$157.94

VRC20-000180brbr1BR · 1BA · Sleeps 6 · 30-Night Minimum · Kayak & Paddleboard Launch · Two Heated Pools · Tennis Court · 5-Min Walk to Manatee Beach · Condo Application Required · For Sale — Showings with 24-Hr Notice · 2 Parking SpacesbrbrImportant before booking: West Bay Cove 226 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.brbrAlso before booking: West Bay Cove 226 requires a minimum stay of 30 nights and a condo application — contact IVP to start the process before booking.brbrA one-bedroom condo in Holmes Beach with a kayak and paddleboard launch located in the northeast corner of the property — direct water access for guests who want to explore Anna Maria Sound without leaving the complex. Two heated pools, a tennis court, and an outdoor sitting area are also available within the community.brbrThe unit sleeps six with a queen bed in the primary bedroom, a sofa sleeper, and bunk beds — a practical configuration for a small family or mixed group staying a month or longer. Flat-screen TVs in the living room and bedroom. High-speed WiFi included.brbrManatee Beach on the Gulf is a 5-minute walk. Publix, CVS, shops, and restaurants are all within easy walking distance. The free Anna Maria Island trolley stops nearby — a car is not needed for daily island life.brbrWest Bay Cove 226 requires a 30-night minimum stay with parking for two vehicles. Condo application required. Not pet-friendly.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

West Bay Cove 226 · Kayak Launch · For Sale

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$371.51

Our five unit property was featured in the January/February 2020 issue of Southern Living, and we are honored and thrilled! brbrWelcome to our Cottage! This listing is the north side of the duplex. If you are looking for a simple, quiet, stress-free place to enjoy the beach, this is it. It's not a fancy condo-- no long hallways, distant parking, elevators, or crowds. Best of all, the cottage is beachfront, so there are no streets to cross-- just a sandy walk through the dunes. The Cottage is a duplex, and this listing is for the smaller side. VRBO #77482 will show you the larger side. The two sides share a screened porch facing the beach. brbrThe cottage was constructed in 1916 or so, as a caretaker's home for a larger house which is now gone. It has been carefully maintained and updated, but has retained the charm of a bygone era. brbrThe interior walls are heart pine, and so are the floors, refinished by hand. Furnishings have been chosen for comfort-- a rattan recliner and matching pillow top queen size sleeper sofa in the living room, dining table for two, and king size bed in the bedroom. brbrIt's shaded by ancient Australian pine trees and has a comfortable shared screened porch for a front-row view of the sunsets and stars. With the windows open at night, you can hear the surf! brbrWalk directly out the screen porch door, and down to the beach--no streets to cross. Or, sit out on the patio and enjoy your coffee and newspaper, or cocktails. Our guests tell us that the best part of the patio area, (besides the view) is it's size-- plenty of room for spreading out. brbrWe are located a block away from the Cafe on the Beach, convenient for all-you-can-eat pancake breakfasts, quick lunches, and relaxing dinners. The beach-front playground is a block and a half away. Take the free trolley and see the rest of the island. brbrIf you need more room, the other side of the duplex, VRBO 77482 is available. Also see our other VRBO listings on the same property, VRBO 82848, 1473396, and 738184. brbrKeywords: Cottage, Duplex, Bungalow, Apartment, Flat

Cottage

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$349.97

This complex at 7100 Gulf Drive is well managed, impeccably maintained and has a reputation of being one of the island's best! brbrEnjoy the white sandy beach directly in front of the complex, soak in the recently renovated community pool, or play a game of tennis (courts have lights). The complex is on the island's free trolley route and there is a stop just up the street on 78th and Gulf Drive. The trolley makes it easy to hit up the local shops, grab a bite to eat or to just sit and enjoy the scenery as you travel the length of the island. brbrThis 2nd floor, end unit has two bedrooms, two bathrooms and is fully furnished. The condo was updated with new flooring, granite countertops, area rugs & some new furniture in December of 2021. The main/master bedroom has a king sized bed and attached bathroom. This bathroom was renovated in October of 2019. The second bedroom is furnished with two twin sized beds and offers quick access to the second bathroom. Televisions are located in the master bedroom and living room. The kitchen is well-equipped with everything you need for basic cooking. The private terrace offers a glimpse of the Gulf of Mexico and is perfect for eating breakfast or enjoying a glass of wine in the evening! We have beach chairs for you to use. If you need additional chairs, you can ask the onsite property manager.brbrThe complex has a laundry room, so it's possible to do your laundry on site. The unit has one reserved parking spot, but additional parking is available.br

Ocean Front ~ No Streets To Cross! Come And Enjoy A Memorable Beach Vacation!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$165.47

Rent one or all three units! THE Marlin is a triplex building. Unit 202 has one bedroom, one bath with a king bed and a sleeper sofa. . brUnit 204 (VRBO #331207) is a two-bedroom one bath unit with a queen bed, two twins and a queen sleeper sofa. brUnit 206 (VRBO # 1128353) is a two bedroom one bath unit with a queen bed, two twins and a queen futon. brRent all three units! Perfect for weddings, family reunions or gatherings. brThis property is zoned as a seven-day rental. brThe building has a large parking area that can accommodate a boat and trailer and both public boat ramps are no more than a 2-minute drive away.brWe are located just one block behind the grocery store, shopping and dining. The public beach is less than a block away. You can't beat the location!brThere is also an outdoor kitchen with a charcoal grill, sink and refrigerator and an outdoor sitting area with tables and chairs.brThe Marlin is located at the corner at 36th Street and 4th Avenue and because it is not a through way and because there is no public parking, the street is hardly traveled and perfect for children.brOur pool is 31'X19'. It has a shallow end with a bench around the perimeter for sitting. The deep end is a large circle perfect for swimming and there is a 'beach' shelf which mimics sitting at the edge of the shoreline. Inside the beach when unoccupied is a fountain and when occupied is a jet that created bubble rings. The pool has a four-color light system which can be solid or multicolor and illuminates the pool for night enjoyment. Also, there is a HUGE deck around the pool with lounge chairs and tables.brArriving late & don't have time to shop Would you like your beverages to already be nice and cold for you when you arrive We can have all of this ready when you arrive. Our fee is $25 plus 10% cost of the groceries.brDo you need bicycles, baby items, beach items, a golf cart Fun and More on the Island is a great place to rent any item you need. funandmorerentals.com They will deliver everything and pick up. It can all be there waiting for you. Tell them you are a VIP guest at the Marlin, and you will receive a 10% discount!brYou 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 propertybrThe town has asked us to include these items.brThis property is zoned as a seven day rental. br2 guest maximumbr2 parking spotsbrVRC16-000284brnoise ordinance-br65 dBA during the hours between 7:00 AM and 10:00 PMbr50 dBA during the hours between 10:00 PM and 7:00 AM

Apartment

One bedroom 1 bath, pool, steps to Beach! Rent one unit or all three!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$728.85

brIN THE EVENT OF A MANDATORY EVACUATION DUE TO A STORM/HURRICANE GUESTS WILL RECEIVE A FULL REFUND.brbrWaves Edge South is one of two very unique homes situated directly on the sugar white sands of Anna Maria Island. Welcome to a dreamy island which oozes the charm of ‘old’ Florida and will remind you of yesteryear when you were young and the pace was a little slower. A place where visitors and residents are as likely to use a bicycle or a golf cart as hop in a car. An Island where the warm waters will soothe your soul and you will leave longing to return once more.brThis lovely 3 bedroom 2 bathroom home enjoys a wonderful location nestled among the sea oats on the beach surrounded by shimmering aqua waters. The Island has miles of beautiful beaches to walk, look for shells, or just sit and enjoy the captivating sunset. Just a stone’s throw from the house you will find shops and restaurants. Additionally, close by you will find stops for the free Island Trolley, which runs the length of the island seven days a week from 6 am to 10 pm. As long as you have your shoes, you can ride for free.brInside you will find a spacious open floor plan which features a fully equipped kitchen with granite counter tops from where you can enjoy sweeping views of the Gulf. Meals can be enjoyed in the inside dining area or out on the expansive deck where there is plenty of seating and you can enjoy the Gulf breezes while you cook out on the gas grill.brIn the cozy, comfortable living area, your family can have lots of fun watching movies on the flat screen TV which also has a DVR/DVD player. Or cuddle up on the sofa and read a book while looking out to the beach through a wall of windows.brThe master bedroom, with a private entrance from the deck, has a king bed with flat screen tv and en suite bathroom with walk-in shower. The first guest bedroom has a queen size bed, flat screen tv and you can step out onto the balcony and enjoy gorgeous beach views. The third bedroom has a twin/full bunk bed, flat screen tv and beach views. There is a guest bathroom with a combination bath/shower.brThe home has a fun sleeping loft with two twin beds and beach views and is suitable for older children and teenagers.brFrom the outside deck, steps lead down to a beautiful heated swimming pool with plenty of loungers for you to relax. brThere is parking for 4 cars. brThe pool and laundry facilities are shared with our sister home, Waves Edge North, which accommodates 6 people. For a large family gathering, why not rent both homes brSee Waves Edge North at http://www.vrbo.com/1405945brAs a courtesy to our guests we heat the pool from December to April. There will be days when the weather conditions will not allow pool heaters to accommodate swimming and temperature recovery times will vary.brWhile the pool is heated during the winter months, we do occasionally get cold spells that can send the temperatures down into 60's and 50's. This will cause the pool water temperature to drop and the pool pump will no longer be able to heat the pool, and it automatically shut down temporarily as a safety feature.brbrWe look forward to welcoming you to our piece of paradise.brPlease note that Waves Edge South accommodates a maximum of 6 guests including children. We are not able to accept guests under the age of 3.brWhen requesting to book the home please be sure to provide the correct number of guests who will be staying which includes adults and children and also the ages of any guests under 25 who will be staying. Thank you.brbrHolmes Beach has a 7 day rental requirement.brbrDue to unforeseen events that could disrupt your travel, we strongly recommend affordable travel insurance to protect your vacation investment. Cancel for an Reason policies are available through Seven Corners Travel Insurance Company and also Nationwide Insurance. In the event that you need to cancel, the travel insurance will refund 75% of the trip and we will refund the additional 25% if you have purchased Cancel for any Reason Insurance. Please ask us for further details.brbrbrVRC17-000021

TOES IN THE SAND! GULF FRONT HOME WITH HEATED POOL, GORGEOUS!

Holmes Beach, Florida, United States

3

Bed

2

Bath

6

Sleeps

$778.27

Relax in this comfy, coastal home just a block from the beautiful beaches of Anna Maria Island. The Blue Sky Beach House is one side of a newly constructed private duplex, with it's own pool, spa and backyard oasis. Decorated in a bright, beachy style, this house has 5 bedrooms and 4 bathrooms, 6 flat screen TV's, private heated pool and spa, stainless steel appliances, grill, rooftop deck, 10 foot ceilings and top of the line amenities. Kids will enjoy the bunk room made just for them...and it's an easy one minute walk to the beach. The open floor plan allows for everyone to be together whether you're in the kitchen, living room or dining area and the pool is completely private (both sides have their own pool)!brbrPerfectly located just a block from the beach and a short stroll to the shops and restaurants, Blue Sky Beach House is ideal for a larger group or multiple families traveling together. It has everything you'll need for a comfortable, relaxing, stress-free vacation. Even an outdoor shower to wash away the sand after a trip to the beach. You won't want to leave!brbrDBPR License number: DWE5105228brHolmes Beach Rental Business License: RBT15-002brMax Occ: 10 Parking: 4 Min Rental: 7 nights

Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$285.26

Step into the tranquil elegance of Hal's Haven, a delightful two-bedroom, two-bathroom retreat nestled in the heart of Holmes Beach. As you approach, you’ll be greeted by a cozy, inviting space that seamlessly blends modern amenities with the laid-back charm of Florida living. brbrThe primary suite features a luxurious king bed with a TV for your entertainment, and its ensuite bathroom offers the luxury of double sinks and walk in shower. The second bedroom boasts a comfortable queen bed. The guest bathroom is conveniently located just outside of the guest bedroom and has a tub/shower combo. brbrThe open-concept living area is designed for comfort and relaxation. In addition to the spacious living room there is a Florida room complete with a queen sleeper sofa that effortlessly transforms the space to accommodate your entire group. The fully equipped kitchen includes all new stainless appliances and all the necessary cookware and utensils, ensuring that preparing meals is a breeze. You'll also find a coffee maker, toaster, blender, and a propane grill, perfect for those alfresco dining experiences.brbrOne of the standout features of Hal's Haven is its private outdoor oasis. Step outside to your heated outdoor pool, where you can cool off on hot summer days or enjoy the Florida sunshine by the poolside. The beautifully landscaped lawn and garden provide a serene backdrop, while the outdoor furniture and beach chairs are perfect for lounging or dining al fresco. brbrConvenience meets luxury with high-speed WiFi, smart TVs, and an array of premium amenities, including beach towels, beach gear, and a washer and dryer. The property also provides secure keyless entry.brbrHal's Haven is ideally located near many popular attractions. Explore the pristine beaches, or take a short bike ride away to the Anna Maria Historical Park for a glimpse into the area's rich heritage. For dining, the nearby area offers a variety of restaurants and casual eateries. Adventure seekers will love the nearby activities like kayak and paddleboarding, parasailing or jet skiing. brbrWhether you’re seeking a romantic getaway, a family vacation, or an active adventure, Hal's Haven promises a memorable stay. Book your perfect Holmes Beach escape today and experience the best of Florida living.brbrPET POLICY INFORMATIONbrbrThere is a $150 taxable pet fee per dog.brAll pets require approval after booking.br ulli iBe sure to indicate you have a pet, where you enter the number of guests/i/li/ulbrIf approved, the fee will be added, and we'll confirm the new total with you before charging your card.brbrFinally, a quick reminder of our pet rules:brulliPets are not allowed on the furniture. /librliThe yard must be kept clean of waste. /librliExcessive hair must be cleaned up prior to departure./libr/ulbrbrPools: Fran Maxon Real Estate is not responsible for pool temperatures, closures or malfunctions. No credit, discount and/or rate adjustment can be granted for items mentioned above or circumstances beyond our control. There will be days when the weather conditions will not allow pool heaters to accommodate swimming and temperature recovery times will vary. brbrVRC18-000162 - Local ordinances require guest stays of at least 7 nights.brbrOnsite parking for 2 vehicles. brbrNoise Notice as required by The City of Holmes Beach:brYou 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. Quiet hours are from 10pm- 8am.

Modern Coastal Home, Private Pool, Close to the beach with beach gear and grill

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$497.13

Looking for the ultimate beachfront vacation experience Look no further than Cool Breeze, a stunningly remodeled 2 bedroom, 2 bathroom condo rental in Holmes Beach!brbr*Features include* brbr* Beachfront condo complex br* 2 full bedrooms and 2 bathroomsbr* Modern kitchenbr* Balcony with full beach viewbr* Plenty of room to sleep 6br* Washing machine in unitbr* Public laundry room with pay washer/dryerbr* Beautiful heated community pool^br* Tennis and Pickleball courtsbr* Premier Holmes Beach locationbr* One (1) assigned parking space brbrLocated in a small complex right on the beach, this spacious and beautifully appointed condo boasts everything you need to make your stay comfortable, luxurious, and unforgettable. From the stunning gulf views to the community pool just steps away, you'll find yourself surrounded by the very best that Anna Maria Island has to offer.brbrInside, you'll find modern and comfortable furnishings, as well as all of the amenities you need to make your stay as enjoyable as possible. From a fully equipped kitchen to high-speed internet and cable TV in every room, you'll have everything you need to feel right at home.brbrCool Breeze features two bedrooms and two full bathrooms ensuring that you and your guests have plenty of space to relax and unwind. The master suite features a king bed and attached private bath. The second bedroom also offers a king bed and shares the hallway bathroom. With the bonus den that includes a queen bed, this condo can sleep up to 6 people comfortably. Please note this den is separated from the main living area by a privacy curtain.brbrOf course, the real star of the show is the breathtaking beachfront location. Whether you're relaxing on your private balcony with table for two or taking a dip in the community pool, you'll enjoy views of the beautiful Gulf waters. With direct access to the beach, you can spend your days swimming, sunbathing, or simply strolling along the sand. (Please see important pool disclaimer below.)brbrDon't miss out on the chance to experience the very best of Anna Maria Island beachfront living. Choose Cool Breeze and start planning your dream vacation!brbr^IMPORTANT: When the air temperature drops below 70 degrees the HOA will close the pool with the solar cover. Unfortunately this is the decision of the HOA and Beach Boutique Rentals has no control over the issue. Additionally the HOA has the right to close the pool for any reason and Beach Boutique Rentals has no control over this decision.brbr* Please note this condo allows 1 assigned parking space and additional guest parking is available on a first come, first served basis. Please keep in mind that if the elevator becomes inoperable for any reason, the stairs will be only way to access the unit.brbrADDITIONAL 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. brbrVRC23-000039 brbrThis 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.

Cool Breeze by Beach Boutique Rentals

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$221.97

West Bay Point Moorings 42 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. VRC#20-000124br Distance to the Beach: 7 blocksbr Community pool.br Please ask for Long-term specials. br br Relax and enjoy the tranquility of West Bay Point Moorings with its panoramic view of Tampa Bay. br Your vantage point for these spectacular views is a condo located in the unique Anna Maria Island resort style complex of West Bay Point & Mooring, tucked away in the City of Holmes Beach.br br br Your remodeled and spacious Island retreat hosts a coastal flair throughout with master and guest bedrooms featuring luxury linens and en suite baths. Open your floor-to-ceiling rear slider doors and a soft breeze will flow through your master suite and beyond! The gourmet kitchen with its full array of items and view-line of the waterfront will enhance your cooking experiences. br br In addition, you will enjoy the complex's amenities that include lush tropical landscaping, a heated swimming pool, and tennis courts.br *This condo association does not permit motorcycles, trailers, large trucks, or RV parking on their property.br br Anna Maria Island is a tropical barrier island seven and one half miles long. Its fine white sugar sand beaches are open to the public with convenient accesses along the entire island. It is one of the finest beaches in the United States. Unlike some tourist areas of Florida that are typified by endless rows of high rise apartment buildings and hotels, Anna Maria is an island of homes and small resorts.br br 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 propertybr Amenities Include:br - # Bedrooms: 2br - Bed Sizes: King, Kingbr - Sofa Sleeper: trundle bed in guestbr - # Baths: 2br - Tub or Shower: t/sh and showerbr - Balcony: Deckbr - Pool: 2 Community poolbr - Pool Heat Avail: Yesbr - #of units in complex: 6br - Tennis: Yesbr - Square Feet: 1458br - Floor Number: groundbr - Distance to Beach: 7 BLOCKSbr - Internet: wifibr - View: Bayoubr - washer dryer: yesbr - Dishwasher: yesbr - Boat Dock: Yesbr - Maximum Persons: 6br - TV: yesbr - Phone: yesbr - Hairdryer: yesbr - Type of Parking: open

West Bay Point Moorings 42 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$328.36

Welcome to Bamboo Apartments #4, a freshly renovated ground-level one-bedroom, one-bath hideaway just 75 steps from the Gulf—no streets to cross, no stairs to climb, and no crowded hallways. A short stroll through our wildflower meadow leads you to soft white sand, gentle Gulf breezes, and spectacular sunsets.brbrFamily-owned since 1971 and featured in Southern Living, our boutique beachfront property blends Old Florida charm with modern comfort. After surviving Hurricane Helene, we invested in thoughtful renovations while preserving the cozy character guests have loved for generations. Our property remains safe, spotless, and lovingly maintained—with no hidden or “junk” fees, ever.brbrSet on nearly an acre of pristine shoreline, Bamboo Apartments offers 150 feet of private beachfront and six spacious patios for grilling, lounging, or simply soaking in the views. If you forget something, your apartment is just steps away—perfect for families with little ones.brbrWhy You’ll Love It Herebrbr✔ Newly renovated after Hurricane Helenebr✔ Just 75 steps to the Gulf – no streets to crossbr✔ Private patio + shared Gulf-front patios with grills & loungersbr✔ King bed with high-quality linens + queen sleeper sofabr✔ Fully equipped kitchen with full-size appliancesbr✔ Complimentary beach gear: chairs, umbrellas, towels, coolerbr✔ Strong Wi-Fi for work or streamingbr✔ Walk to Skinny’s Burgers, Two Scoops Ice Cream, Publix, Walgreens & the free Island Trolleybr✔ Family-owned since 1971 | Featured in Southern Livingbr✔ No hidden fees—everbrbrYour Outdoor Paradise:brbr• Five breezy Gulf-front patios shaded by towering Australian pinesbr• Charcoal grills for the perfect beachside cookoutbr• Beach gear provided—just pack your swimsuit and sunscreenbr• Outdoor shower & clothesline to rinse off after the beachbr• On-site coin laundry located in our historic cistern housebrbrCome experience the best of Anna Maria Island: where “Old Florida” charm meets modern comfort, and where you’re always just steps from the sand, sunsets, and relaxation.brbrTraveling with others and need more space Check out our other listings: VRBO 77482, VRBO 82848, VRBO 1473396, and VRBO 327896. brbrKeywords: Duplex

Apartment

Cozy Ground-Level Beach Retreat – 75 Steps to the Gulf | Bamboo Apts #4

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$412.08

Endless Summer By Anna Maria Life Vacation Rentalsbr210 56th St, Holmes Beach, FL 34217brbrWhat You'll Love About This Home:brRecently RenovatedbrLocation! 1.5 Blocks to the Beach!br4 Bedroom / 3 Bathroomsbr3 Kings / 2 TwinsbrPrivate Heated PoolbrPool LoungersbrOutdoor ShowerbrGas BBQ GrillbrBackyard Covered Verandah with Patio Dining for Six plus Lounge SeatingbrCorn Hole GamebrProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels, Beach Chairs & Beach WagonbrFenced YardbrParking for 3 CarsbrDetails:brbrSun & fun await at Endless Summer. Located in a prime location in Holmes Beach with a short stroll to shopping, the public library, restaurants from casual to upscale, various bars and entertainment, Endless Summer is a fantastic quiet place to enjoy your unforgettable and relaxing vacation.brbr Our luxury vacation home features a sparkling private pool and is a block and half or 2 minutes' walk to the sandy beaches of the Gulf of Mexico.brbrTwo of the king bedrooms feature en-suite bathrooms with a rainfall water feature in the walk-in shower. A third king bedroom and guest room with two XL twin beds share the hall bathroom. Each bedroom has a TV and includes crisp linens and plush towels from our professional linen company. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrThe living and dining area are open and airy. Your family and friends will enjoy the comfortable couches and large screen TV. The chef in your family will love the kitchen with stainless-steel appliances and induction range. A large dining table seats eight with additional covered outdoor patio dining for six with plenty of space to sit under shade. Step outside and fire up the gas grill and enjoy the island life.brbrImmerse yourself in the ultimate retreat as the pool and covered patio have recently been upgraded with exquisite marble pavers. The sparkling heated pool is the perfect spot to relax in a pool lounger and enjoy a dip while enjoying an afternoon of tranquility in your island paradise. The outdoor shower provides an added convenience to wash off the sand from your trips to the beach. Your unforgettable vacation awaits!brbrEndless Summer is an easy walk 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, Ensuite Bathroom, TVbrBedroom 2: King, Ensuite Bathroom, TVbrBedroom 3: King with TVbrBedroom 4: Twins with TV brbrPlease note:brPets are not allowed in this home.brAmenities are subject to change.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.brbrVRC16-000152brbrIMPORTANT 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.

Endless Summer: Sparkling Pool, 2 Blocks to Beach, Fenced Yard by Anna Maria Life Vacation Rentals

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$325.28

This quaint cottage is located on the beach - 3007 Avenue F Unit 3 at 30th Street on beautiful Holmes Beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4. The cottage is hidden away on a dead end street away from it all, yet close to shopping and restaurants. brbrThe unit has a full shower with tub plus a shared outdoor shower, spacious kitchen and a compact washer/dryer. The grounds are filled with exotic, tropical plants and a private guest path to the beautiful blue water and white sand beaches of Anna Maria Island.brbrThere is a free trolley that picks up throughout the day and evening located just one block away. The unit is centrally located between Bradenton Beach and Anna Maria where there are several shopping areas and many restaurants. St. Armand's Circle, Robinson Preserve, Bradenton's Riverwalk, DeSoto National Park and Ringling Museum all make for great local day trips!brbrJoin us at Holmes Beach for the most beautiful sunsets and experience the tradition of Old Florida.brbrThese are older, charming units built in the 50's that we continually update. Housekeepers clean at the beginning and end of each guest stay.br brCan't beat the gulf views and the sunsets....brbrIf the downstairs unit is not available, please check the upstairs unit at Vrbo #737839.brbrKeywords: Beachhouse, condo, duplex, cottage, beachfront rental

Cottage

Pelican Perch: Tropical Paradise Cottage on the Beach VRC17-000167

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$432.59

Holmes Beach code compliance VRC16-000645 ST lic DWE5105216brThis gorgeous home is just short distance to the beach, with other beautiful homes nearby. This beautiful home is one of two, with zero lot line construction, so the adjoining house has just common wall in the garage, this home has its own separate backyard, heated pool 82-84 degrees & Jacuzzi(not a hot tub) and views from the balcony. This home is a two bedroom, so can sleep 4, but does have a sleeper sofa in the living room for 2 extra guest. The Living room is located upstairs and gives a great view of the beach and Gulf of America. There is a deck off the Living room with great breeze coming off the gulf, and fantastic location to watch the sunsets. This home has a private pool, with a paver deck, surrounded by Palms, and all types of Florida Landscaping. The Living room and dining room and Kitchen are all located together, all with a view of the beach. Relax back, watch a movie on Flat screen TV, or get on your laptop and scroll the internet.brPrivate garage for parking out of the weather and secure when your gone. There is an elevator that will take you to all levels, or take the stairs your choice. Bedrooms are very spacious, with a large shower and walk in closets for the Master bedroom. Master bedroom has a King size bed, large flat screen TV, and a deckbrwith a partial view of the gulf. Second bedroom has a small deck over looking the pool area.brAnna Maria Island has miles of white sandy beaches, fishing piers, all types of rentals (boat, Seadoo's, Segway's, Para Sailing, bikes, list goes on...) Free Trolley rides all over the Island. There are fine Restaurants, shoppes, markets, and so much more!!! Please note prefer Saturday to Saturday in high season times in winter and summer If you have additional small children you can request infobrbrKeywords: On Anna Maria Island, Holmes Beach. Two story home above garage, View of the beach, Private garage with elevator, 3 decks, Private Kidney shaped pool, Kitchen with Stainless steel appliances, Granite counter top, Wood cabinets, King size Bed, High speed Internet, Elevator, Miles of white Sandy beaches

Gorgeous Home July specials check it out, heated pool and spa, elevator

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$315.07

Just Bring You to this beautifully appointed bright beach condo. Feel the island vibe with modern beachy furniture with comfortable beds just steps from beach with elevator, 2 bedrooms, 2 bathrooms, 2 porches (1 screened-in), 3 bikes and everything (really, everything!) you need for a happy, relaxing beach getaway! Rest by the beach or pool and take an elevator to your modern cottage-style beach condo with washer-dryer, dishwasher, a Guest Room with 1 Full and 1 Twin bed and a Master Bedroom with 1 super comfortable King bed. Park easily in your spot in the covered garage. On beach side of Gulf Drive, so you don't even have to cross the street and you are toes-in-the-sand in minutes! Our porch looks out to trees on the side of the building. Walk down and take a short well-manicured path to beach. Well-maintained heated pool and tennis courts. Close to stores (Publix, CVS), restaurants (like Hurricane Hanks, The Sandbar, Blue Marlin, The Waterfront, The Beach House, our faves!) and minutes to walk to *FREE* trolley stop (runs until 10p). Enjoy 3 Flat screen TVS - 1 per bedroom and 1 in living room, all with Cable. Free WiFi. Fresh furnishings, towels (bath and pool towels) and bedding. Guest Bathroom Reno completed December 2025 ; Brand new Washer / Dryer December 2025. Master Bedroom Reno Jan 2022. We are available by text, phone and email to answer any of your Qs at any time. We love it here on AMI, and you will too! Great for couples and families (supplied with a pack and play, board games and a bin of toys) and perfect for celebrating anniversaries and birthdays - we've hosted many Anniversary and Birthday celebrations! 1 Labeled 103 parking spot, Additional Guest parking spots. Please Note Per Holmes Beach: 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. LICENSE # VRC17-000175

Happy, Beachy Holmes Beach Condo Tennis, Heated Pool, Elevator Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$385.0

For your relaxing and family fun, Anna Maria Island vacation, check out this spacious beautiful 3 bedroom, 2.5 bath town home. Coastal furnished and surrounded by tropical landscape with 2 balconies and a community pool. Enjoy wonderful sunrises and make memories to last a life time!brbrWhen you arrive at the North Beach Village complex, you'll find this end unit conveniently located just a short walk from gulf beaches and the Holmes Beach town center. Shopping and dining within walking distance, but parking for two vehicles in the garage makes it easy to take the whole family across Anna Maria Island. brbrWhen you aren't busy exploring Holmes Beach, head over to the heated shared pool for a swim, or lounge on one of the patios with a good book. The ground floor patio is brand new with a cozy fire pit. Inside, this vacation rental offers coastal furnishings and entertainment via the flat screen TV and free Wi-Fi. The fully equipped kitchen and dining room nicely accommodate all, with the screened lanai just through the sliding doors off the living room. A gas BBQ grill is also provided for the grill masters.brbrAccommodates up to 6 people. Minimum Stay Required: 1 Week. brDogs welcome! Max of 2 and the pet fee is $200 per pet plus taxes.brMax. parking: 2; VRC 19-000147brbrYou 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.brbr* Cancellation more than 90 days prior to arrival will receive a deposit refund less a $250 cancellation fee. Cancellation less than 90 days prior to arrival will forfeit all deposit received. Cancellation less than 60 days prior to arrival will forfeit all monies on account. Cancellations must be confirmed in writing.

Spacious 3 bedroom town home on Anna Maria Island, community pool.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$241.19