Vacation Rentals By Owner In Holmes Beach, FL

Looking for a spacious and secluded place for you and your family You have found it!brbrThis unit in Sandy Pointe is well appointed and has fabulous views of Grassy Key, a natural preserve of mangroves. Bird watchers bring your binoculars! This complex is set off the main road, away from bright lights and will offer clear views at night for the stargazers. brbrThe ground floor has a two car, tandem parking, garage. It stores all the beach equipment you could ask for as well as a ping-pong table for family enjoyment and friendly competition. brbrOne floor up you have your main living area, kitchen, dining room, full bath and guest bedroom with twin beds. There are two balconies on this floor. One facing east for beautiful sun and moon rises and one on the west side for lovely sunsets.brbrOn the third floor is the master bedroom ensuite that is very spacious and offers a work space among the tree tops. If you have to work, you will be surrounded by nature and comfortable quiet space. The second guest bedroom has a full size bed and another balcony for views of the nature preserve and sunsets.brbrAll of this within minutes to shopping, eateries, grocery and Most importantly the Beach! The free trolley stop is just outside the entrance to take you to other areas of our Island Paradise. brbrThe heated swimming pool is just outside your front door. There are plenty of tables, chairs and loungers to enjoy the sun. There is also a pool side changing room, if needed.brbrAmenities Include:brbr- View: Mangroves/Tree topsbrbr- Beach Distance: 2.5 blocksbrbr- Pool, Heated: Yesbrbr- Beach Access: Publicbrbr- Pool: Yesbrbr- TV Cable/Satellite: 3 TV's/Cablebrbr- Internet Access: Yesbrbr- washer dryer: Yes/Stackbrbr- Bed Size 1st/Master: Kingbrbr- Bed Size 2nd Rm: Fullbrbr- Bed Size 3rd Rm: 2 Twinsbrbr- Beds Pull-out: Yesbrbr- Floor No.: 2 living levels above garagebrbr- Parking: Two car garage (tandem)brbr- Patio: Open air balconybrbr- Balcony: Two-One east and one westbrbr- Bbq Grill: Yes, gasbrbr- TVs/Vcr/Dvd: 3brbr- Furnished: Yesbrbr- Master Bath Features: Walk-in showerbrbr- Walk-In Shower: Yes. Twobrbr- Community Features: Poolbrbr- Garage: Yesbrbr- Bus Service Avail.: Publicbrbr- Minimum Stay: One weekbrbr- Agent: Lisa Varanobrbr- Office: Anna Maria Islandbrbr

Sandy Pointe #114 ~ Beach, heated pool, Preserve

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$471.49

Island Beach Club 1 - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. VRC16-000745br Beach/Gulf Front - Community Pool with new heat pumpbr Max 1 vehicle.br Please ask for Long-term specials. br br Updated, with new furniture and dcor in a 'Tommy Bahama' style. You'll love the peaceful, relaxing new look. This is the only 2 bedroom 2 bath condo with a private, full size washer and dryer. The master bedroom has a new queen size bed.br The guest bedroom has 2 twin beds which can be put together to become a king bed. The kit for this is in the condo. br br You will arrive to complete comfort and all the essentials needed. Guests also have the use of Alexa. It makes it so easy to ask about the weather and neighborhood restaurants. All you have to do is say, Hi Alexa. 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. Easily explore, taking advantage of the free trolley, with stops the length of the island.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 property.br br Island Beach Club Association Rules-2025/2026br Island Beach Club Association Has No Onsite Management- All Rentals Are Managed by Owners/ Agents. If you have any problems or questions, please contact the Rental Owner/ Agents from whom you rented from.br br General Rules-br No Pet are Allowed in the unit or on Island Beach Club Premisesbr Cars must be parked so they do not obstruct the walkways. Each Unit is permitted to one car on the shelled lot.br No Gulf Carts are allowed on premises.br Skateboards and roller-skates may not be used on the association property. br Per Holmes Beach Fire Rules-Cooking Grills may not be used on balconies, on walkways or in parking lots. br There is only one designated grilling area, and each user should try to keep grill and grill area clean. br Children cannot be left unattended. They are not allowed to play on public balconies and stairways.br Towels, clothing, etc. may not be hung over balcony railings.br Balconies or walkways in front of units or on side of buildings may not be blocked.br No Rowdy or Disruptive Behaviorbr Nothing can be left outside during Hurricane Season if the Unit is Unoccupied.br All Tenants must abide by the four- person occupancy limit per rental unit, and guest of these tenants should be limited and closely monitored. Guests may park at the north end of the building only. br Trash Rules-br Please bag and tie garbage to reduce odorsbr Empty your trash in the community dumpster provided at the rear of the propertybr br Swimming Pool and Swimming Pool Area-br The Pool is open from Dawn to Dusk br Only tenants and their guests are allowed. Guests must be accompanied by a tenant staying on property.br Tenant use of the pool is limited to four persons per unit, tenant / groups greater than four persons are welcome to enjoy our private beach and the Gulf of Mexico. br Children 12 and under must be accompanied by an adult whenever in the pool area.br No Running, Roughhousing or horseplay in the pool areabr No throwing anything in the pool areabr No Glass IS ALLOWED in the pool areabr All users are required to clean up after their use and properly arrange the pool furniture when leaving.br All state and county rules that are posted on the sign must be observed.br Amenities Include:br - # Bedrooms: 2br - Bed Sizes: Q, 2 tw-w/King kitbr - # Baths: 2br - Tub or Shower: 2 showersbr - Balcony: screened in lanaibr - Pool: Community poolbr - Pool Heat Avail: Yes new heat pumpbr - #of units in complex: 10br - Square Feet: 984br - Floor Number: ground levelbr - Distance to Beach: gulf frontbr - Internet: yes-wifibr - View: gulfbr - washer dryer: yesbr - Dishwasher: yesbr - Maximum Persons: 4br - DVD/VCR: yesbr - TV: yesbr - Phone: yesbr - Hairdryer: yesbr - Type of Parking: 1 spot in lotbr - Coffee maker: Drip and K-Cupbr - Blender: Yes

Island Beach Club 1- Anna Maria Island-Condo 2 Bedroom/2 Bath gulf front, maximum occupancy of 4 people.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$274.14

Fountain Head, Unit 6 - Anna Maria Island - 2 Bedroom / 1.5 Bath, maximum occupancy of 4 people. VRC16-000061br Community pool. br Distance to the Beach: 1 blockbr Please ask for Long-term specials. br br Part of a perfectly-sized 8 unit complex, you'll have parking for two vehicles and access to the complex pool and back-yard grilling area. Just off the pool deck there is a coin operated washer/dryer.br br br The property is centrally located in the City of Holmes Beach. Enjoy many activities on your visit; swimming, snorkeling, beautiful sunsets, fishing, boating, sunset dining, picnicking, shopping, watching wildlife, golfing, bicycling, tennis, and more. Easily explore the island on the free trolley.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 Please Remember: You are vacationing in a residential area where homes are in close proximity to each other. Please be a good neighbor by keeping the noise to a respectful level during the day and night. A violation of the city's noise control ordinance shall subject the violator to the issuance of a notice of violation or citation. Noise is measured at the property line of the property generating the noise.br Amenities Include:br - # Bedrooms: 2br - Bed Sizes: Queen, Twinsbr - # Baths: 1.5br - Tub or Shower: Full/ 1/2 bathbr - Balcony: Yesbr - Pool: Community poolbr - Pool Heat Avail: Yesbr - #of units in complex: 8br - BBQ Grill: Communitybr - Square Feet: 900br - Floor Number: Townhousebr - Distance to Beach: 1 Blockbr - Internet: WiFibr - View: Poolbr - washer dryer: Yesbr - Dishwasher: Yesbr - Maximum Persons: 4br - DVD/VCR: Yesbr - TV: Onn 44' in living roombr - Hairdryer: Yesbr - Type of Parking: 2 spaces under bldg.br - Coffee maker: Keurigbr - Blender: Yes

Fountain Head 6 - Condo 2 Bedroom / 1.5 Bath , maximum occupancy of 4 people. Holmes Beach Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$243.58

Sandy Point 111 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$363.88

Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath, maximum occupancy of 4 people. br Gulf/Beach Front - Community Poolbr Please ask for Long-term specials. br br Max 1 vehicle.br VRC16-000067 br Island Beach Club is a 10 unit building with a new heat pump heated, shared pool. br br Enjoy many activities on your visit; swimming, snorkeling, beautiful sunsets, fishing, boating, sunset dining, picnicking, shopping, watching wildlife, golfing, bicycling, tennis, and more.br Easily explore, taking advantage of the free trolley. There are convenient stops the length of the island.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 property.br br Island Beach Club Association Rules-2025/2026br Island Beach Club Association Has No Onsite Management- All Rentals Are Managed by Owners/ Agents. If you have any problems or questions, please contact the Rental Owner/ Agents from whom you rented from.br br General Rules-br No Pet are Allowed in the unit or on Island Beach Club Premisesbr Cars must be parked so they do not obstruct the walkways. Each Unit is permitted to one car on the shelled lot.br No Gulf Carts are allowed on premises.br Skateboards and roller-skates may not be used on the association property. br Per Holmes Beach Fire Rules-Cooking Grills may not be used on balconies, on walkways or in parking lots. br There is only one designated grilling area, and each user should try to keep grill and grill area clean. br Children cannot be left unattended. They are not allowed to play on public balconies and stairways.br Towels, clothing, etc. may not be hung over balcony railings.br Balconies or walkways in front of units or on side of buildings may not be blocked.br No Rowdy or Disruptive Behaviorbr Nothing can be left outside during Hurricane Season if the Unit is Unoccupied.br All Tenants must abide by the four- person occupancy limit per rental unit, and guest of these tenants should be limited and closely monitored. Guests may park at the north end of the building only. br Trash Rules-br Please bag and tie garbage to reduce odorsbr Empty your trash in the community dumpster provided at the rear of the propertybr br Swimming Pool and Swimming Pool Area-br The Pool is open from Dawn to Dusk br Only tenants and their guests are allowed. Guests must be accompanied by a tenant staying on property.br Tenant use of the pool is limited to four persons per unit, tenant / groups greater than four persons are welcome to enjoy our private beach and the Gulf of Mexico. br Children 12 and under must be accompanied by an adult whenever in the pool area.br No Running, Roughhousing or horseplay in the pool areabr No throwing anything in the pool areabr No Glass IS ALLOWED in the pool areabr All users are required to clean up after their use and properly arrange the pool furniture when leaving.br All state and county rules that are posted on the sign must be observed.br Amenities Include:br - # Bedrooms: 2br - Bed Sizes: King-new and twinsbr - # Baths: 2br - Tub or Shower: 1 T/ 1Showerbr - Balcony: Screened porchbr - Pool: Community poolbr - Pool Heat Avail: Yes new heat pumpbr - #of units in complex: 10br - Square Feet: 984br - Floor Number: Second floorbr - Distance to Beach: Gulf frontbr - Internet: Yes wifibr - View: Gulf-Beach frontbr - washer dryer: onsite coin operatedbr - Dishwasher: Yesbr - Maximum Persons: 4br - DVD/VCR: Yesbr - TV: (L)(M)br - Hairdryer: Yesbr - Type of Parking: 1 spot in lot

Island Beach Club 21 - Anna Maria Island - Condo 2 Bedroom / 2 Bath gulf front , maximum occupancy of 4 people.

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$298.31

Fountain Head, Unit 8 - Anna Maria Island - 2 Bedroom / 2 Bath, maximum occupancy of 6 people. VRC16-000062br Community Poolbr Distance to the Beach: 1 blockbr Please ask for Long-term specials. br br Part of a perfectly-sized 8 unit complex, you'll have parking for two vehicles and access to the complex pool and back-yard grilling area. Just off the pool deck there is a coin operated washer/dryer. br br br The property is centrally located in the City of Holmes Beach. Enjoy many activities on your visit; swimming, snorkeling, beautiful sunsets, fishing, boating, sunset dining, picnicking, shopping, watching wildlife, golfing, bicycling, tennis, and more. Easily explore the island on the free trolley.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 Please Remember: You are vacationing in a residential area where homes are in close proximity to each other. Please be a good neighbor by keeping the noise to a respectful level during the day and night. A violation of the city's noise control ordinance shall subject the violator to the issuance of a notice of violation or citation. Noise is measured at the property line of the property generating the noise.br Amenities Include:br - # Bedrooms: 2br - Bed Sizes: New Queen, 2 twinsbr - Sofa Sleeper: Yes queenbr - # Baths: 2br - Tub or Shower: Full/showerbr - Balcony: Yesbr - Pool: Community poolbr - Pool Heat Avail: Yesbr - #of units in complex: 8br - Square Feet: 900br - Floor Number: Elevated Townhousebr - Distance to Beach: 1 Blockbr - Internet: Wifibr - View: Peek of Gulfbr - washer dryer: onsite-coin operatedbr - Dishwasher: Yesbr - Maximum Persons: 6br - DVD/VCR: Yes/Yesbr - TV: (L)(M)br - Phone: yesbr - Hairdryer: yesbr - Type of Parking: Under Bldg

Fountain Head 8 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Holmes Beach Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$391.83

Beach Bliss by Beach Retreats Vacation Rentalsbr 320 64th Street, Holmes Beach, FL 34217br 3 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub | Walk to Beach | Pet-Friendlybr VRC17-000113br✨ Fully Renovated February 2025 ✨brWelcome to Beach Bliss, a beautifully updated 3-bedroom, 3-bathroom bungalow just minutes from the white-sand beaches of Anna Maria Island. With a private backyard oasis, modern finishes, and a prime Holmes Beach location, this home is the perfect island escape for families, couples, and groups of friends.br While most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!br HighlightsbrNewly renovated in 2025 – everything fresh and modernbrJust a short walk to the beachbrHeated private pool & hot tubbrOutdoor lounge space with sun & shade seatingbrPet-friendly – up to 2 dogs allowed (with fee)brIncludes 4 beach chairs, umbrella & beach wagonbrFree AMI trolley stop only 1 minute awaybr Inside Your BungalowbrBedroom 1: King bed + ensuite bathroombrBedroom 2: King bed + ensuite bathroombrBedroom 3: Two twin beds with hall bath accessbrGourmet kitchen with stainless steel appliances & everything you need to cook at homebrSpacious, open living area with Smart TV and cozy seatingbrDining area for family meals or game nightsbr Your Backyard OasisbrLarge, heated pool & spa with plenty of space for loungingbrOutdoor dining & seating areas for BBQs, cocktails, or quiet mornings with coffeebrFenced backyard for privacy & petsbr Explore Anna Maria IslandbrFree Trolley: hop on just steps from the home and explore the island car-freebrStroll to local favorites: The Waterfront, Skinny's Burgers, The Sandbar, and morebrNearby activities: parasailing, sunset cruises, paddleboarding & bike rentalsbrEasy access to Bean Point, Bridge Street & boutique shopsbr Pet-Friendly StaybrBring your furry friends along—Beach Bliss welcomes up to 2 dogs (with $150 non-refundable per-pet fee). Please disclose pets at booking.br Booking & CancellationbrNo cancellation fees!brCancel 60+ days before arrival → Full refundbrCancel within 60 days → No refundbrExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundablebr$500 deposit due at booking; balance due 60 days priorbrFor reservations 21+ nights or $20,000+ → 10% deposit due at time of booking.brThird party travel insurance cost is due at time of purchasebrThird-party travel insurance through Beach Retreats is non-refundablebrNo changes permitted within 60 days of arrival or during staybrWe highly recommend cancelation insurancebr This home can accommodate up to 3 vehiclesbr Quiet hours at 10p-7a: please respect neighborsbr✨ Whether it's a sun-soaked beach vacation, a family retreat, or a pet-friendly getaway, Beach Bliss offers the perfect Anna Maria Island escape.br Book now at BeachRetreatsFL.com

Beach Bliss managed by Beach Retreats FL Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$450.65

If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than Sunny Side of the Beach on 66th Street. This five bedroom, 3 bathroom island paradise, nestled into the city of Holmes Beach, is equipped with a beautiful, state of the art kitchen fully supplied with all the cookware, appliances and other kitchen supplies to allow for the full expression of your inner gourmet chef. The home is beautifully decorated with understated beach house elegance throughout. The five bedrooms-each of them comfortable, cozy and bright-are arranged for maximum privacy, with flat screen TVs and cable access. brbrConveniences abound here: the washer and dryer are top of the line, and Wi Fi gives you complete internet connectivity throughout the house. The spacious living and dining areas are perfect for getting together after a day at the beach. Or, lounge together by the heated pool and miniature waterfall while grilling on the gas grill on the patio, secluded by beautiful native landscaping and adorned by the finest in patio furniture. brbrOne of the world's most beautiful beaches is just a few steps-yes, literally just a few short steps, less than a block away-from the front door. The sunsets over the Gulf horizon are breathtaking. If you're in the mood to go out, you're just a short bike ride away from all of the best shopping, dining and sight-seeing that Anna Maria Island has to offer. Indeed, cozy and comfortable meet luxury and convenience at Sunny Side of the Beach on 66th Street. You and your family and friends will experience the vacation of a lifetime here.brbrBedroom 1: King with TV on Floor 1brBedroom 2: King Master with TV on Floor 2 brBedroom 3: King with TV on Floor 3brBedroom 4: King with TV on Floor 3brBedroom 5: 2 Twin-over-Twin Bunk Beds on Floor 1br*The bed configuration was recently updated in the fall of 2022 and may not be reflected in the photos.brbr*Please note: 4 cars maximum are able to 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.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.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.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrVRC16-000209

Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$362.73

Sun, Sand & Style at Holmes BeachbrbrRelax in this beautifully furnished 3-bedroom, 2.5-bath townhome with a private pool, just an 8 min walk to the beach! brbrSpend your days soaking up the sun, sailing on the Gulf, shopping, or golfing nearby—and enjoy the convenience of walking to local restaurants and beach bars.brNOTE: there are two separate rental units as noted in the listing (A and B) and EACH has it's OWN Private POOL.brbrThe SpacebrBedrooms: King bed in bedrooms 1 & 2, 2 twin beds in bedroom 3brHome Features: 4 Smart TVs, soaking tubs, chandeliers, board games, modern décorbrOutdoor Fun: Fenced pool with tanning chairs, furnished patio with dining set & gas grillbrKitchen: Fully equipped with stainless steel appliances, breakfast bar, essentials, and spicesbrGeneral: Free WiFi, washer & dryer, central AC & heating, towels & linens providedbrbrParking & Extrasbr- Driveway fits up to 4 vehicles br- No parking on the streetbr- Ring doorbell security camera (front exterior only)br- No Electric Golf Carts / Gas Golf Carts Only (no parking on the street)brbrHouse Rulesbr- Check-in: 4 PM | Check-out: 10 AMbr- No smoking, pets, events, or large gatheringsbr- Guests must be 25+ to bookbr- Stairs required for access; may be challenging for limited mobilitybrbrEscape to Holmes Beach for a worry-free getaway with all the comforts of home—and a little extra sunshine!brbrLooking for more space brAnother 3-bedroom home for up to 6 guests is available on-site—ask about booking both for larger groups.

Chic Holmes Beach #B Private Pool

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$424.94

Island Luxury Near the Beach | Private Pool & PatiobrbrEnjoy the best of Holmes Beach in this bright and stylish 3-bedroom, 2.5-bath home on beautiful Anna Maria Island & only an 8 min walk (or 2 min car ride) to the beach!brbrDesigned for relaxation, this coastal retreat features an open layout, high-end finishes, and a tropical backyard oasis complete with a private pool, grill, and plenty of lounge space. brNOTE: there are two separate rental units as noted in the listing (A and B) and EACH has it's OWN Private POOL.brbrStroll to local beaches, grab a bite at nearby cafes, or explore the island by bike. Whether you’re planning beach days, golf outings, or sunset cocktails, this home makes it easy to unwind and enjoy it all.brbrHighlights:br- Private fenced pool with sun loungers and outdoor diningbr- Fully equipped kitchen with stainless appliances and island seatingbr- 4 Smart TVs, board games, and cozy tropical décorbr- Two king bedrooms + twin bedroom for flexible sleeping arrangementsbr- Washer/dryer, free WiFi, central A/CbrbrGuest Notes:br- Gas only Golf Carts allowed (no street Parking)br- Driveway parking for 4 cars (no street parking)br- No pets, smoking, parties, or eventsbr- Must be 25+ to bookbr- Exterior Ring doorbell camera (front entry only)br- Stairs required for access

Chic Holmes Beach #A Private Pool

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$872.72

Island Escape by Beach Retreats Vacation Rentalsbr 307 65th St, Holmes Beach, FL 34217br VRC18-000047brYour dream getaway awaits on Anna Maria Island! This stunning 4-bedroom (+ bonus room), 4-bath luxury vacation home is just steps from the beach and close to the best dining, shopping, and island attractions. With a private heated pool featuring a waterfall, waterslide, and shaded lounge area, this home is the perfect mix of relaxation and fun for families and groups.brWhile most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!br Highlightsbr Steps to the beachbr Private heated pool with waterfall, waterslide & grottobr Covered pool deck with outdoor TV & grillbr 5 bedrooms, 4 bathrooms br ‍ ‍ Perfect for large families & groupsbr Luxe linen service includedbr Free high-speed WiFibr Walk to restaurants, shops & the free island trolleybr This home can accommodate parking for up to 3 vehiclesbr Inside Your RetreatbrThis spacious and beautifully designed home features a bright open floor plan with high-end finishes throughout. The living area includes cozy sofas, a large Smart TV, and direct access to the outdoor pool deck.brThe fully equipped gourmet kitchen is stocked with stainless steel appliances, service for 12, and everything you need to enjoy home-cooked meals. A spacious dining area makes gathering for breakfast or dinner effortless.br Room DetailsbrMaster Suite: King bed, ensuite bathroom with dual sinks, walk-in closet.brBedroom 2: King bed, attached bathbrBedroom 3: King bed, ensuite bathroombrBedroom 4: King bed, shared bathbrBunk Room: 2 bunk beds (4 twins) with charming clapboard walls & bead-board ceilings — a fun kids' hideaway!brWith four King bedrooms and a bunk room, there's plenty of space for everyone to spread out while still enjoying time together.br Outdoor LivingbrThe backyard is your private tropical oasis. Spend your days splashing in the heated pool with grotto, waterfall, and waterslide, or relax on the covered pool deck while catching the game on the outdoor TV. Fire up the grill and enjoy meals al fresco under the shade.brBeach days are a breeze with provided gear including a beach cart, 4 chairs, umbrella, and wagon.br Location & Things to Dobr Steps to the free Anna Maria Island trolleybr Walk to award-winning restaurants like Chateau Anna Maria, The Feast, and Duffy's Tavernbr Live music, bars & shops within walking distancebr Activities include parasailing, paddleboarding, fishing, sunset cruises & morebrWhether you're chasing adventure or simply soaking up the Florida sun, this home places you right in the heart of it all.br✅ Important InfobrMax occupancy: 10 guestsbrNo cancellation fees!brCancel 60+ days before arrival → Full refundbrCancel within 60 days → No refundbrExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundablebr$500 deposit due at booking; balance due 60 days priorbrFor reservations 21+ nights or $20,000+ → 10% deposit due at time of booking.brThird party travel insurance cost is due at time of purchasebrThird-party travel insurance through Beach Retreats is non-refundablebrNo changes permitted within 60 days of arrival or during staybrWe highly recommend cancelation insurancebrGuests must be 25+ to book (or accompanied by parent/guardian)br Quiet hours: 10 PM – 7 AM; please respect neighborsbr Book your stay at Island Escape today and experience the best of Anna Maria Island — where coastal elegance meets fun in the sun! brWe prefer Saturday to Saturday rentals. If you're looking to stay other days, please give us a call.

307 65th Street managed by Beach Retreats FL Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$464.83

306 67th Street Unit B Holmes Beach, FL 34217brVRC 19-000277br Caribbean Surf by Beach Retreats Vacation Rentalsbrbr Holmes Beach, Anna Maria Islandbr 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-Friendlybrbr✨ Your Anna Maria Island Bungalow Retreat ✨brWelcome to Caribbean Surf, a bright and inviting 3-bedroom, 2-bath bungalow just a short stroll from the sugar-white sands of Holmes Beach. With its cozy coastal charm, private heated pool, and family-friendly amenities, this home is the perfect place to relax, unwind, and enjoy everything Anna Maria Island has to offer.brbr While most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!brbr HighlightsbrbrShort walk to Holmes BeachbrbrPrivate heated pool in your own fenced backyard oasisbrbr Pet-friendly + family-friendly yard space (Non refundable pet fee of $125/pet)brbrGrill, lounge chairs, and beach gear includedbrbrFree Wi-Fi, washer/dryer, central A/Cbrbr Inside Your HomebrbrBedroom 1: King bed + ensuite bathbrbrBedroom 2: King bedbrbrBedroom 3: Two twin bedsbrbrSpacious living area with flat-screen TV and comfortable seatingbrbrFully equipped kitchen for family meals and island dining nightsbrbr Outdoor LivingbrbrHeated pool with sun loungers and tropical landscapingbrbrPrivate fenced yard — perfect for kids or petsbrbrGrill + outdoor dining area for BBQ nights under the starsbrbrBeach chairs, umbrella, and wagon provided for seaside adventuresbrbr Explore Anna Maria IslandbrbrFrom Caribbean Surf, you're just minutes away from:brbrThe vibrant shops & eateries of Pine AvenuebrbrLocal favorites like Ginny's & Jane E's Café and The Sandbar RestaurantbrbrIsland adventures: fishing, kayaking, paddleboarding, biking, and dolphin toursbrbr Booking & CancellationbrbrNo cancellation fees!brCancel 60+ days before arrival → Full refundbrCancel within 60 days → No refundbrExtended stays & bookings $20,000+ → Full payment 90 days prior, non-refundablebr$500 deposit due at booking; balance due 60 days priorbrFor reservations 21+ nights or $20,000+ → 10% deposit due at time of booking.brThird party travel insurance cost is due at time of purchasebrThird-party travel insurance through Beach Retreats is non-refundablebrNo changes permitted within 60 days of arrival or during staybrWe highly recommend cancelation insurancebrbr This home can accommodate 2 vehiclesbrbr✨ Whether you're lounging poolside, strolling to Holmes Beach, or exploring the island's hidden gems, Caribbean Surf is your perfect home base for an unforgettable Anna Maria Island vacation.brbr Book now! br This home features Silicon Travel. With Silicon Travel's firewall place in place, you can prevent internet access to any malicious activity in a Vacation rental home. Any guest device (WebCam, Baby Monitor, etc) can be added for a set time and will be removed automatically upon departure.

Caribbean Surf managed by Beach Retreats FL Anna Maria Island

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$441.02

You, Me, and the Sea AMI by AMI Locals brVRC21-000081 brbrWelcome to You, Me, and the Sea AMI by AMI Locals, your perfect family retreat on beautiful Anna Maria Island. Just a one-minute walk to the soft Gulf sands, this elevated three-bedroom, two-bath vacation home blends modern coastal design with laid-back island comfort. Thoughtfully designed for families and multi-generational groups, it offers spacious living, a private pool with spa, and a prime Holmes Beach location close to everything that makes island life unforgettable. brbrHighlights br• 1-minute walk to Holmes Beach br• 3 Bedrooms / 2 Bathrooms br• 2 Kings / 1 Queen / 1 Full-over-Full bunk with Twin trundle br• Private pool with in-ground spa br• Balcony with outdoor dining and BBQ grill br• 2-minute walk to the Anna Maria Island trolley stop br• Parking available for 4 vehicles brbrStep into paradise with your very own private heated pool and spa, surrounded by lush tropical greenery that invites total relaxation. The balcony features a shaded dining area and grill, perfect for sharing alfresco meals and sunset cocktails after a fun-filled beach day. brbrInside, you’ll find a bright open floor plan designed for comfort and togetherness. The living room offers cozy seating and a TV for movie nights, while the fully equipped kitchen features stainless steel appliances, generous counter space, and a dining table set for family gatherings. A small workspace next to the kitchen provides a convenient spot to catch up on emails or jot down vacation plans, making this home functional as it is relaxing. Whether preparing breakfast or enjoying evening dinners, this space makes island living effortless. brbrThe primary suite is ideal for parents and kids, featuring a king bed, full-over-full bunk bed with twin trundle, and an ensuite bathroom with a double vanity and walk-in shower. The second bedroom includes a king bed, while the third bedroom offers a queen bed. Both share a hallway bathroom with a walk-in shower, making it easy for everyone to have their own space and comfort. brbrRoom Details br• Primary Bedroom (2nd floor): King bed, Full-over-Full bunk with Twin trundle, ensuite bathroom with walk-in shower br• Second Bedroom (2nd floor): King bed br• Third Bedroom (2nd floor): Queen bed br• Hall bathroom with walk-in shower brbrThis home provides a washer and dryer, Wi-Fi, and beach essentials for guest use. Guests can easily explore Anna Maria Island with the island trolley, just steps away. Located near restaurants such as Skinny's Place and Double Deez Chicago Style Restaurant, or parks like Grassy Pointe Preserve, you’ll have local dining and outdoor activities at your fingertips for the perfect island experience. brbrFrom peaceful mornings on the balcony to sunset swims in the pool, You, Me, and the Sea AMI by AMI Locals offers everything you need for an unforgettable Anna Maria Island vacation rental. Make lifelong memories with your loved ones and book your stay today! brbr- brThis home is managed by AMI Locals, an Anna Maria Island property management company. 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. 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 Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise respectful 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.

You, Me, and the Sea AMI - Elevated Beach Home with Pool and Spa Steps from Beac

Holmes Beach, Florida, United States

3

Bed

Bath

6

Sleeps

$313.6

Welcome to The Seaside 21, your private waterfront retreat on beautiful Anna Maria Island. Nestled in the heart of Holmes Beach, this fully renovated villa offers the perfect blend of island charm and modern comfort.brbrStart your mornings with coffee on your private dock, watching the sun rise over the peaceful bayou. Just four short blocks from one of the Gulf’s most pristine beaches, you’re never far from the sugar-white sand and turquoise water.brbrBring your boat or let a local captain pick you up dockside for a day of fishing, island hopping, or a sunset cruise. When you’re ready to explore, restaurants, shops, and cafés are just a short stroll away, with the rest of the island easily accessible by bike or golf cart.brbrWhether you’re seeking adventure or relaxation, The Seaside 21 is your gateway to the laid-back luxury of island life.

Villa

Stylish waterfront villa in the heart of Holmes Beach on Anna Maria Island.

Holmes Beach, Florida, United States

Bed

Bath

4

Sleeps

$764.31

Summary:brbrCoconuts Unit 117 features a king bed, 2 queen beds, a queen sleeper sofa, full bathroom with tub/shower, professional linen service, fully stocked kitchen, 75 smart TVs in the living room & bedroom, and a private balcony with gulf views! brbrLocated in a poolside complex with a heated shared pool, BBQ grill, beachfront/poolside loungers, and 2 dedicated parking spaces—all just steps from the beach! Perfect for a relaxing coastal getaway—just bring your sunscreen and unwind!brbrbrbrThe Space:brbrWelcome to Coconuts – Your Beach/Poolside Getawaybrbrbrbr✦ VRC21-000176brbrbrbrStep into paradise at Coconuts, a beautifully appointed second-level, poolside unit, steps aways from the beach with unbeatable views, ultimate convenience, and all the comforts of home. Perfect for couples, small families, or anyone looking for a relaxing coastal retreat, this two-bedroom gem sleeps up to four guests comfortably.brbrbrbr✦ Rest EasybrbrAs you enter, you’re greeted by a spacious king bedroom and another bedroom with 2 queen beds. Each feature a luxurious mattresses to ensure restful sleep after your beach days. We partner with a professional linen service, so you’ll arrive to fresh, hotel-quality bed linens, plush bath towels, and beach towels – no need to bring your own. brbrbrbr✦ Comfort & ConveniencebrbrThe hallway houses a clean, modern bathroom with a tub/shower, and the unit has a washer and dryer in it!brbrbrbrThe fully equipped kitchen has everything you need – whether you’re preparing a gourmet dinner or quick beach snacks. Featuring stainless steel appliances, a drip/Keurig combo coffee maker, full-size fridge/freezer, microwave, dishwasher, oven, and all the essential cookware and utensils.brbrbrbr✦ Open Living with Stunning ViewsbrbrEnjoy uninterrupted gulf views from the open-concept kitchen, dining area, and living room. The living room features a queen sleeper sofa, perfect for additional guests, and a 75” smart TV – mirrored by another in the master bedroom. Log into your favorite streaming services and unwind after a sun-filled day.brbrbrbr✦ Relax OutdoorsbrbrStep through the sliding glass doors onto your own balcony.brbr It’s the perfect place to sip your morning coffee or relax while the sun melt into the horizon each evening.brbrbrbr✦ Resort-Style AmenitiesbrbrGuests have access to a heated, shared pool, complete with poolside barbecue grills and comfortable patio furniture – a great way to cool off or gather for a laid-back meal. You are steps away from the beach!brbrbrbrWhether you're celebrating a honeymoon, anniversary, birthday, or simply in need of a quick weekend escape or an extended beachside stay, Coconuts has it all.brbrbrbrBook your stay today and make memories that last a lifetime at Coconuts 117~Beachside Paradise!brbrbrbrGuest Access:brbrCoconuts features beautifully maintained shared grounds with lush tropical landscaping. During your stay, you’ll have access to a shared swimming pool and convenient propane barbecue grills—perfect for relaxing or enjoying a meal outdoors.brbrbrbrOther Things to Note:brbrFor your convenience, the home includes 2 beach chairs, , a beach umbrella, and all the bath towels, beach towels, and linens you'll need—everything ready for a relaxing stay!brbrbrbr2 cars maximum is able to park in the two dedicated 117 parking spaces. For any over flow there is parking on the road. Always remember to park the way of traffic with all 4 tires off the pavement. We ask our guests to please plan accordingly and coordinate with your group.brbrbrbrPlease 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.brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m here to help! You can call or text me directly on my cell. I’m available 24/7 to answer questions, offer local tips, or assist with anything that comes up. Your comfort is my priority!

Gulf View ~Heated pool~Renovated~Coconuts 2 bed!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$366.25

Top Reasons to Book:br-Only 1.5 Blocks to the Beachbr-Private Pool with Swim-Up Tiki Table (Free Pool Heat in Cooler Months)br-3 Bedrooms + Sleeper Sofa – Sleeps Up to 6br-All Bedrooms Have Ensuite Bathroomsbr-Fully Equipped Kitchen with Island Seatingbr-Multiple Outdoor Spaces Including Front Deck & Private Backyardbr-Close to Manatee Public Beach, Dining, Shops & Free AMI TrolleybrbrWelcome to Blue Martini, a bright and inviting two-level beach home just steps from the Gulf. Vaulted ceilings, tropical backyard views, and an open living area create a relaxing coastal retreat. The fully equipped kitchen features stainless steel appliances, ample counter space, and island seating—perfect for meals and entertaining.brbrThree comfortable bedrooms each include an ensuite bathroom, and the primary suite features a private balcony and walk-in shower. A sleeper sofa in the living room provides flexible accommodations.brOutside, enjoy your own private oasis with a heated pool, swim-up tiki table, loungers, and a gas grill for fresh island meals. Multiple dining areas—indoors and out—let you take advantage of the island breeze all day long.brbrManatee County Beach is minutes away, along with great restaurants, shops, and access to the free island trolley. Enjoy kayaking, paddleboarding, tours, golf, boat charters, and all that Anna Maria Island has to offer.brbrBedrooms & Baths:br-Primary Bedroom, 1st Floor: King bed, TV, private balcony, ensuite bath with walk-in showerbr-Second Bedroom, 1st Floor: King bed, TV, ensuite bath with walk-in showerbr-Third Bedroom, 2nd Floor: Queen bed, TV, ensuite bath with shower/tubbr-Living Area: Queen sleeper sofabr (Sleeps 6 total)brbrImportant Notes:br-No Pets Allowedbr-Parking: Max 3 cars (no overnight street or additional parking)br-TVs use Roku for streaming (no traditional cable)br-Complimentary starter kit provided; guests replenish as neededbr-Pool Heat: Free during cooler season

Beautiful 3 Bedroom 3 Bath Home Steps Away from the White Sands of Holmes Beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$320.59

Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will make preparing meals easy. Spend time grilling on the private patio after a day of fun on the beach.You are just a seashell's throw from the white sands of the Gulf of Mexico, it is also only a half-mile walk to ice cream, restaurants, shopping and other local treats.brbrSea Pirate #6 features 2 bedrooms/1 bath and sleeps six with a king-size bed and two sets of twin bunk beds. The large enclosed patio features a gas grill and ample seating for a quiet evening after a day at the beach. This unit also has a washer/dryer.brbrOur Professional Linen Program: SeaBreeze Vacation strives to bring only the best quality experience to our guests— including a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you high-quality linens that are in place and ready for your use upon your arrival. These premium linens are laundered in a commercial setting that uses only hypoallergenic, perfume- and dye-free soaps assuring all guests a comfortable stay. brbrWith all SeaBreeze Vacation properties, we think of the little things to make your vacation special. Included to get you started are the following: brbrPer Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Pool/Beach TowelbrPer Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Shower Products Set (including trial size shampoo, conditioner, shower gel, and body lotion), Cosmetic Cloth, Bath MatbrPer Kitchen: 2 Rolls of Paper Towels, Hand Soap, Dish Soap, Sponge, Dishwasher Pods (x4), Laundry Detergent Pods (x4), All-Purpose Disinfectant, Microfiber Cloth, 2 Kitchen TowelsbrbrWe also offer a range of supplemental services including pre-stock grocery shopping and babysitting. Need a pack and play or high chair, etc. These are available for a small additional fee and will be waiting in the home on your arrival.brbrCancellation Policy - SeaBreeze Vacation has spent a great deal of time and effort into formulating a cancellation policy for you. SeaBreeze Vacation has the most flexible cancellation policy on the Island. You are allowed to cancel your reservation up to 14 days prior to check-in to receive a refund. Additional terms and conditions apply. Please note: For reservations longer than 28 nights or more than $20,000, a different cancellation policy applies - please see the Rental Agreement under the House Rules on the check-out page.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.brbrCity of Holmes Beach Vacation Rental License: VRC16-000818brMax Occupancy: 6 Guests | Max Vehicles: 1brQuiet Hours: 10 p.m. - 7 a.m. - please respect our island communitybrMin stay requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.

Steps to Beach - Sea Pirate Unit 6 by SeaBreeze Vacation

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$384.11

Cuddlefish Cove Your flip flops have found a new retreat by the beach! Stay for a week or a month at this dazzling Key West inspired, 3 bedroom beach house with New heated pool, all within minutes from the most amazing beach on the Gulf of Mexico. You will feel relaxed within minutes of arriving! brbrThe morning sun illuminates the open sitting and dining area where large ceiling fans provide a relaxing breeze that you’ll come to love at Cuddlefish Cove. The large, well appointed kitchen with fully equipped stainless steel appliances is inviting and the long island bar is where friends and family will gather. Looking for that perfect place for afternoon cocktails Sneak away to the rooftop deck with fabulous views of the Gulf of Mexico and Tampa Bay. brbrAs a place to be inspired and relaxed you’ll find all the amenities of home including: large screen TV, DVD, wireless internet, and washer/dryer. Enjoy your afternoon siesta in one of three bedrooms with all new ensuite bathrooms, comfortable beds and walk out decks. The main floor master suite with luxury mattress king bed has a gorgeous Juliet balcony to enjoy the tropical breeze. The main floor boasts two bedrooms one with a king size bed and walk in shower and the other bedroom with twin beds and full bath. brbrA new heated pool surrounded by a garden full of palms and hibiscus is perfect to enjoy the sun as well as a covered lanai by the pool is perfect for those who want to get out of the sun! A perfect blend of interior meets the outdoors with relaxing patio furniture and a large flat screen television. brbrTake a walk, bike or free trolley to the village and stop in one of the beach side cafes, Ice-cream, or boutiques, famous piers and so much more! Take the virtual tour and see why Cuddlefish Cove will become your family and friend’s special place on the Island. Sleeps six.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.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.br*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrVRC16-000222

Cuddlefish Cove: Heated Pool, rooftop deck, gorgeous views!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$187.38

266 South Harbor - Anna Maria Island - 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC# 20-000032br No Pool - Distance to the Beach: 3 blocksbr Please ask for Long-term specials. br br This elevated home is in the city of Holmes Beach. Nice open floor plan with spacious kitchen and new stainless steel appliances. The two car garage features one side long enough to accommodate a truck with a boat trailer. Take advantage of the roomy deck. Visit and relax with friends and family.br Grill the day's catch, and dine under the stars.br br Enjoy many activities on your visit: swimming, snorkeling, beautiful sunsets, fishing, boating, shopping, watching wildlife, golfing, bicycling, tennis, and more. The free island trolley has convenient stops the length of the island.br br You are vacationing in a residential area where homes are in close proximity to each other. Please be a good neighbor by keeping the noise to a respectful level during the day and night. A violation of the city's noise control ordinance shall subject the violator to the issuance of a notice of violation or citation. Noise is measured at the property line of the property generating the noise.br Amenities Include:br - # Bedrooms: 3br - Bed Sizes: Queen, twinsbr - Sofa Sleeper: Futon in denbr - # Baths: 2br - Tub or Shower: bothbr - Balcony: Yes-largebr - #of units in complex: single homebr - Tennis: public nearbybr - BBQ Grill: yes Gas grillbr - Square Feet: 1522 / 3646br - Floor Number: elevated homebr - Distance to Beach: 3 blocksbr - Internet: wifibr - View: neighborhoodbr - washer dryer: Yesbr - Dishwasher: Yesbr - Boat Dock: neighborhoodbr - Maximum Persons: 6br - DVD/VCR: Yes-Blue Raybr - TV: living room,master,dbr - Hairdryer: yesbr - Type of Parking: 2 car garagebr - Coffee maker: yes regularbr - Blender: yes Ninja

266 S. Harbor - Anna Maria Island- Private home 3 Bedroom/ 2 Bath , maximum occupancy of 6 people.

Holmes Beach, Florida, United States

1

Bed