Holmes Beach Vacation Rentals on Anna Maria Island
Vacation Rentals by Owner in Holmes Beach on Anna Maria Island .
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Captain's Quarters: 1 Block to Beach, Dog Friendly, Pool
Captain's Quarters Spinnakers by Anna Maria Life Vacation Rentals
202 56th St #1, Holmes Beach, FL 34217
What You'll Love About This Home:
Location! 1 Block to the Beach!
3 Bedrooms / 2 Bathrooms
3 King Beds
Heated Pool - Shared
Pool Loungers & Adirondack Chairs
Outdoor Shower
Gas Grill
Patio Dining
Cornhole
Washer & Dryer - Private
Complimentary WIFI
Dog Friendly - with pet fee - see info below
Beach Towels & Beach Chairs
Parking for 2 Cars
10.0 Star Review
3 Bedrooms
- Sleeps 6
Holmes Beach Vacation Rental
Pets Allowed 
Beach pool House Family Vacation Home.
This is a privately owned side by side property, nothing is shared . Private driveway/ garage / Pool and fenced in back yard.
Home away from home, cozy and comfortable Beach house. A 5 minute walk to the beach and shops. Very quite neighbor hood.
New elevated house with private heated pool, and fenced in yard, with a large swing.
King bed in the master bedroom with its own bathroom ,queen bed in the second bedroom, and two twin beds in the third bedroom . Second bathroom located in t.......
Paradise Palms: Paradise Awaits, Heated Pool, Perfect Location!
***Updated Photos July 2025***
Step into your own private paradise at this beautifully renovated 3-bedroom, 2-bath getaway, featuring a bonus Den and a 2-car garage—all conveniently on one level. Recently renovated in 2025, the home offers fresh, modern finishes throughout while maintaining a warm and welcoming feel.
The open-concept living area is perfect for gathering with family and friends, with plenty of space to relax and unwind. Step outside to the spacious backyard, where a l.......
Gulf Sands 103, 2B/2B Beachfront condo on Anna Maria Island!
Newly remodeled. Beautiful turquoise Gulf of Mexico waters, 7 miles of white sand beach, your own private balcony overlooking the beach and the water! This condo boasts a king- sized master bedroom with view of the Gulf. XL twins in the guest room with adjacent bath. Undercover parking, LARGE heated pool with new paver deck, 42' HD flat screen television. Wi-fi Internet service, washer/dryer, full kitchen and close to all of the conveniences: shopping and great restaurants and the free tr.......
AMI Tropical Oasis - A private house very close to the beach on a great street
This completely custom remodeled island 3 bedroom 2 bath 2200 sq ft. pet friendly home with a fantastic back yard.
It is just one block (we have a long block) to the beach (short 5 min walk or 2 minute bike/golf cart ride) and centrally located on Anna Maria Island in the city of Holmes Beach on a relaxing super friendly residential street!
While the inside of the home is pristine, gorgeous, and beautifully decorated, the real feature of this home is the outdoor backyard oasis! It.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Holmes Beach Vacation Rental
Pets Allowed
Gorgeous condo one block from Manatee Beach
Welcome to paradise! Enjoy close proximity to beach and everything you could possibly want in newly renovated quiet and safe 2 bedroom 2 bath spacious condo located in Westbay Cove. Laundry in unit. Easily accessible (avoid traffic) and walk to grocery, drug store and numerous restaurants. Community has 2 pools, tennis and pickleball. One designated parking spot and plenty of guest parking. Cable, electric and high speed internet all included in price. Free trolley just outside your door. Only 1.......
10.0 Star Review
2 Bedrooms
- Sleeps 4
Holmes Beach Vacation Rental
Pets Allowed
Updated ground-level Villa, Pet Friendly and so close to the beach! Great Rates!
This cute Villa in Holmes Beach is a perfect getaway nestled in a quiet neighborhood. Come relax for a week in this 2bedroom, 2 bathroom villa close enough to the beach to walk and then relax or enjoy all that Anna Maria has to offer!
The master suite has a king size bed and on-suite shower bathroom. There is a full closet, chest of drawers and table equipped with a charging station. Plenty of storage to unpack and organize for the long week vacation. The guest bedroom has a queen size be.......
9.8 Star Review
2 Bedrooms
- Sleeps 4
Holmes Beach Vacation Rental
Pets Allowed
Beach Walk: North Beach Village, Pool, Quick Walk to Beach by Anna Maria Life Vacation Rentals
Beach Walk by Anna Maria Life Vacation Rentals
6250 Holmes Blvd, #31, Holmes Beach, FL 34217
What You'll Love About This Home:
Location! – Just 2.5 Blocks to the Beach
2 Bedrooms | 2.5 Bathrooms
Sleeping for 6: 1 King, 2 Twins, Queen Sofa Sleeper
Heated Community Pool
Spacious Screened Lanai
Gas BBQ Grill
Professional Linen Service, Washer & Dryer,
Complimentary WIFI, Beach Towels
Beach Towels, Beach Chairs & Beach Wagon
Two Dedicated Parking Spaces
.......
Anna Maria 2 Family Home w/ pool, beach/3 blocks.
Side B is being rented with private use of the pool and private use of all the fenced in area around the pool & unit. Again, the pool and pool area are not shared spaces, and side B truly does come with private use of these areas. Side B is 1325SF, has 3 bedrooms, 2 bathrooms and sleeps 10. Side B is the only side referenced in this listing.
This ranch-style 2 Family Home (duplex) is located in Holmes Beach on Anna Maria Island just 3 blocks from the beach, 1 block from Holmes Beach .......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Holmes Beach Vacation Rental
Pets Allowed
Beach Haven Ranked #204 for businesses in Holmes Beach FL
Beach Haven #204 at Seaside Beach House is favorite for guests of Holmes Beach and Anna Maria Island.
This 1050 sq ft. One Bedroom, One Bathroom, on the beach condo is a welcome haven from the busyness of life. Whether you prefer relaxing by the pool or to walk 20 feet onto the white sands, this condo offers an escape from the world. With a Kingsize Bed and a Queen Sofa sleeper this a perfect family getaway.
Enjoy your morning coffee and evening watching the sunset on the bal.......
Perfect Vacation Home with Pool, Putting Green, and Waterslide
Island Pearl Oasis by AMI Locals
VRC19-000119
Escape to Island Pearl Oasis, a beautifully designed home just steps from the stunning beaches of Anna Maria Island! This luxurious four-bedroom home offers a bonus loft, six-and-a-half bathrooms, a private heated pool with a waterslide and spa, and a rooftop deck with panoramic water views. Located just a short walk to the Gulf beaches and within easy reach of shops, waterfront dining, and parks, this island oasis is perfect for families.......
9.4 Star Review
4 Bedrooms
- Sleeps 8
Holmes Beach Vacation Rental
Pets Allowed
LOW PRICES! Serene AMI Beach Resort Unit 1 Central Holmes Beach, FL
Harbor Lane Court is ideally situated only 300 steps from the Gulf, offering guests four charming ground-floor apartments.
These include three comfortable one-bedroom units and a spacious two-bedroom suite, all beautifully renovated in 2016. Steeped in Old Florida charm, the resort retains its original 1962 terrazzo floors and cathedral ceilings, creating a welcoming and nostalgic atmosphere.
Please refer to our photos for a detailed site plan with unit identification numbers and guest rev.......
LOW PRICES! AMI Beach Resort Harmony Unit 4 Central Holmes Beach, FL
Harbor Lane Court is ideally situated only 300 steps from the Gulf, offering guests four charming ground-floor apartments.
These include three comfortable one-bedroom units and a spacious two-bedroom suite, all beautifully renovated in 2016. Steeped in Old Florida charm, the resort retains its original 1962 terrazzo floors and cathedral ceilings, creating a welcoming and nostalgic atmosphere.
Please refer to our photos for a detailed site plan with unit identification numbers and guest rev.......
LOW PRICES! AMI Beach Resort Sanctuary Unit 3 Central Holmes Beach FL
Harbor Lane Court is ideally situated only 300 steps from the Gulf, offering guests four charming ground-floor apartments.
These include three comfortable one-bedroom units and a spacious two-bedroom suite, all beautifully renovated in 2016. Steeped in Old Florida charm, the resort retains its original 1962 terrazzo floors and cathedral ceilings, creating a welcoming and nostalgic atmosphere.
Please refer to our photos for a detailed site plan with unit identification numbers and guest rev.......
Anna Maria Island - Completely Renovated w/ Private Pool
One level living, the PINK PALM, is a fantastic 2-bedroom, 2-bathroom, Old-World Florida Cottage meets Shabby Chic! Completely renovated in 2025 and private pool, air-conditioning and wi-fi. What else do you need?
Come escape from it all and relax in paradise minutes from public beach access. Quietly nestled between Bradenton Beach and Anna Maria City, this Holmes Beach location is convenient to everything the island has to offer.
Highlights
• Beautifully Decorated
<.......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Holmes Beach Vacation Rental
Pets Allowed
Prefect Beach Villa with private beach and heated pool. Gulf front at its's best
Your Dream Beach House on Anna Maria Island!
Enjoy your vacation in our beautiful beach house, located at the end of a quiet cul-de-sac with one of the few private beaches right outside your door. Experience exclusive beach days in absolute privacy.
The house offers numerous amenities for an unforgettable vacation:
Outdoor Relaxation Area: Unwind by the heated pool with comfortable loungers, an outdoor kitchen, and a pool bar with a covered dining area - perfect for fun even.......
Anthony Beach Cottages - Island Retreat Heated pool home w/ 4 bedrooms 3 baths
Open now! No hurricane damage and post-hurricane upgrades. All photos were taken post-hurricane. Our Island Retreat cottage, situated 3 blocks from the beach and 2 blocks from the bay with a heated pool and secluded yard surrounded by mangroves, is a two story pet friendly home which includes 3 bedrooms on the first floor with the master suite on second floor, cable TV in all 4 bedrooms, washer/dryer, dishwasher, microwave, dishes, linens and towels, porches on both levels to enjoy gulf and bay .......
8.0 Star Review
4 Bedrooms
- Sleeps 8
Holmes Beach Vacation Rental
Pets Allowed
Special rate promotion!!! Luxury canal front!! Completely remodeled!!
Anchorsaway is a Completely renovated canal home, the ultimate in waterfront luxury. No expenses spared on this beautiful new home. Cypress and shiplap ceiling, glass tile, travertine pool deck, wood beams, Viking appliances, Ipe outdoor shower, full house sonos, 5 huge flats screens, bring your boat for the 12k lift, use our kayaks and paddle boards........
10.0 Star Review
3 Bedrooms
- Sleeps 6
Holmes Beach Vacation Rental
Pets Allowed
Gulf Place #8 | Beachfront Condo on Anna Maria Island |Heated Pool | Sunset View | Tennis / Pickleball
**ASK ABOUT LAST MINUTE DEALS!
Wake up to sweeping views of the Gulf of Mexico in this beautifully maintained beachfront condo located in the heart of Anna Maria Island. Gulf Place offers a peaceful, boutique-style coastal retreat just steps from white sand beaches and turquoise water.
The Space
This bright, coastal-inspired condo is designed for relaxation and comfort. Enjoy an open living area with comfortable seating, flat-screen TV, and complimentary WIFI. The fully equi.......
Private Ground Level Beach Paradise
3 bedroom, 2 bath, spacious deck with lovely heated swimming pool. Great for grilling and enjoying the lovely, spacious, lush, tropical landscaping. Located on 2 corner lots affords great privacy. Outdoor, warm water shower. 1 block from the incredible white sands of the Gulf of Mexico. All ground level home. Great laundry room, spacious kitchen and sit down bar. High speed Internet connection and 2 cable TV 's with HD flat screen TV. This is a tobacco-free property. No pets........
Coastal Charm Meets Cottage Chic! Sparkling Pool/Spa *4 Doors To The Beach*
Renovations complete!
**PLEASE CONTACT OWNER PRIOR TO BOOKING TO VERIFY AVAILABILITY**
*RATE QUOTED MAY CHANGE UNTIL BOOKING IS CONFIRMED*
***PLEASE TEXT 8137652323 WHEN SUBMITTING INQUIRIES FOR FASTER RESPONSE***
Need to get away from the frenzy of everyday life??? Come visit us at *Ashore Thing* Beach Cottage on Beautiful Anna Maria Island. Once you arrive you'll see why Coastal Living magazine hails us as a 'Dream Town' with no high rise condos and 35 mph and und.......
1 Block to Beach on Private Lake Heated Pool, SPA 6937 Holmes Blvd.
WE ONLY RENT FROM SATURDAY TO SATURDAY WITH A 7 NIGHT MINIMUM!!
6937 Holmes Blvd, Holmes Beach, FL 34217. Google us for maps for relative location to beach and Gulf.
We installed a new pool with a spa in 2016. This island home just one block from the beach offers a one of a kind setting which affordably gives you the pleasures of a spring-fed lake with dock as well as one block (3 minute walk) to the beach with a peek of the gulf. The beautiful lake is home to all types of fish ranging.......
Canal Front Old Florida Charmer! 2BDRM 2 Full Bath
Welcome to Westbay 203 at Westbay Point & Moorings located Bayside in Holmes Beach! Make yourself at home at this Old Florida charmer with 2 bedroom, 2 bathroom canal front unit!
🏡 Property Highlights:
✨ Heated community pool
✨ Tennis courts and outdoor "living room" with lounge chairs and dining tables
✨ Just a 10-minute walk to the beach!
✨ Unbeatable central location close to grocery store and shops
✨ Primary bedroom: King bed, full bathroom with shower/tub.......
Waters Edge 204S - Gulfview Condo - pool and tennis - By Island Real Estate Vaca
“Water’s Edge 204S” is part of the beach side Water’s Edge Condominiums. These condos are perfectly placed, as you’ll see during your stay. Nestled in the city of Holmes Beach, right off the Gulf of Mexico. Unit 204S is the premiere choice for a coastal getaway. A great place to relax, unwind, and enjoy the island sunsets.
This beachside unit is spacious and can accommodate six. The master bedroom has a king-bed, with amenities such as a flat screen TV and a tub shower combo. T.......
Perfectly Located Near the Beach, Dining, and Shopping!
Saltwater Palms by AMI Locals
VRC21-000078
Welcome to Saltwater Palms, a stylish home located just across the street from Holmes Beach! This two-story, three-bedroom, two-bath duplex offers the perfect blend of comfort, privacy, and outdoor entertaining. Relax on the sundeck, the balcony, or gather with friends around the outdoor, covered BBQ area surrounded by palms. Take a short stroll to the pool, outdoor shuffleboards, the beach, or nearby shops and dining and explore the islan.......
Blue Oasis West! Family-Friendly Duplex Near Shops and Dining
Blue Oasis West by AMI Locals
VRC21-000103
Welcome to Blue Oasis West, a newly remodeled ground-level duplex just a 6-minute walk to Anna Maria Island’s beautiful beaches. This three bedroom, three bath vacation rental features a private saltwater pool with spa, stylish coastal decor, and an ideal location near the island trolley stop. Whether relaxing at home or exploring Holmes Beach shops and restaurants, this home is a perfect choice for your Florida getaway.
Highlights.......
Peaceful Poolside Escape Near Holmes Beach!
Blue Oasis East by AMI Locals
VRC21-000102
Welcome to Blue Oasis East, a beautifully remodeled ground-level home just a 6-minute walk to Holmes Beach on the stunning shores of Anna Maria Island. This bright and breezy three bedroom, two and a half bathroom vacation retreat features a new saltwater pool and hot tub, modern coastal interiors, and a prime location close to local restaurants and bars.
Highlights
• 6-minute walk to Holmes Beach
• 3 Bedroom / 2.5 Bath.......
Forget me Knot - Private Pool Home - By Island Real Estate Vacations
Newly Updated - New bathrooms and updates completed in February of 2023!! “Forget Me Knot” is a gem among island homes. With its location in the heart of Holmes Beach this island oasis is one of the premiere places to stay during your tropical vacation. With a Mediterranean-style, fresh décor, and its placement off the beaten path makes it a secluded paradise.
During your stay at “Forget Me Knot” you’ll find yourself only a short walk away from the beach, 4 minutes! So, take a.......
Sun and Surf – Direct Gulf Front Condo
Vrc19-000071
Need a getaway? We have the perfect spot for you. Welcome to Sun & Surf, a direct gulf front condominium on beautiful Anna Maria Island. This 2-bedroom, 2-bathroom condominium offers all the charm and comforts you will come to expect from a Salty Mermaid Vacation Rental. This unit has no damage from hurricanes Helene and Milton. Perched just steps from the beach, you will have unbeatable access to Anna Maria Island's seven miles of pristine sand and warm Gulf waters. Trade i.......
Beachfront Bliss! Pool, Spa and Sunsets!
Beachfront Bungalow by AMI Locals
VRC19-000270
Welcome to Beachfront Bungalow, a rare four-bedroom, three and a half bath coastal cottage located directly on the sandy shores of Holmes Beach on Anna Maria Island! With nothing but your private pool and spa between you and the Gulf, this beachfront escape is designed for travelers who want more than just a “near the beach” experience. Perfect for up to 14 guests, this home is ideal for family vacations, small weddings, or intimate .......
9.4 Star Review
4 Bedrooms
- Sleeps 8
Holmes Beach Vacation Rental
Pets Allowed
Beachfront Condo! Gulf Views, Pool, and Balcony
Island Paradise #6 by AMI Locals
VRC22-000085
Welcome to Island Paradise #6, a luxury beachfront condo in Holmes Beach on Anna Maria Island! With three bedrooms, two bathrooms, direct beach access, and breathtaking Gulf views, this retreat is perfect for families or couples seeking a relaxing coastal getaway. Enjoy the Gulfside heated pool, easy access to local dining and shops, and modern amenities designed for comfort and style!
Highlights
• Beachfront condo
• .......
Beachfront Condo with Stunning Gulf Views!
Island Paradise #4 by AMI Locals
VPR16-000350
Welcome to Island Paradise #4, a stunning two-bedroom, two-bath beachfront condo that embodies island living! Situated just steps from Holmes Beach’s white sandy beaches, this premium property offers panoramic Gulf views, breathtaking sunsets, and direct beach access. Located centrally on Anna Maria Island, it is close to shops, waterfront restaurants, and grocery stores, your perfect escape to relax, explore, and enjoy this scenic is.......
Gulf-side 1BR--75 Steps to Sand, Private Patio, Family-Owned Since 1971
Step into Old Florida charm with modern comfort at Bamboo Apartments #3, just 75 steps to the sand, with no streets to cross. We survived Hurricane Helene, are newly renovated, and remain meticulously maintained. From your bedroom window, enjoy a peek at the Gulf while the patio outside invites you to grill, lounge, and soak in breezy sunsets. Featured in Southern Living, our family-owned retreat has welcomed guests since 1971. No hidden fees, ever. Walk to Skinny's for a burger, Two Scoops for .......
Anna Maria Island-Beautiful 3/3 Pool Townhome - Our Island Beaches are Calling!
This townhouse is beautifully decorated and completely modernized with everything you need for the perfect vacation in paradise! The townhouse is convenient to everything on the island - walk to the beach, supermarket, retail shops, and restaurants. Or catch the local trolley (or the **golf cart) and cruise the island to a vast selection of top rated restaurants and see all that Anna Maria Island has to offer. Be sure to reach out with any specific questions you might have - we're happy to work .......
9.8 Star Review
3 Bedrooms
- Sleeps 6
Holmes Beach Vacation Rental
Pets Allowed
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Our five unit property was featured in the January/February 2020 issue of Southern Living, and we are honored and thrilled!
Welcome to our Cottage! 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-- and there are no streets to cross to reach the beach--just a sandy walk from your screened porch door. The Cottage is a duplex, and this listing is for the larger side. VR.......
Gulf views from unit and rooftop terrace, 1 minute walk to beach, heated pool.
NOTICE: We are a 7-night minimum stay rental property and licensed by the state of Florida. We are set up for Sat-Sat stays but inquire for any other arrangements you may need in the fall.
We are so fortunate that we were able to complete all of our hurricane repairs on the unit and in the association as well. We are back in business and the beach is in great shape. We also replaced the bedroom rugs with great LVP flooring.
The kitchen has been refinished with new cabinet.......