- 93 properties returned
-
Sort by:
Random
- Name
- Beds
- Beds
- Sleeps
- Sleeps
- Random
- Price
-
Welcome to your Anna Maria Island escape "Pineapple Paradise"! New to the vacation rental market, this beautifully designed 4-bedroom, 5-bathroom home in Holmes Beach is just two blocks from the beach—perfect for families and groups ready to enjoy sun, sand, and relaxation."Pineapple Paradise" is a spacious two-level home offers plenty of room to s
Pineapple Paradise
Home- 4
- 5
- Pool
- No Pets
- Sleeps 8
- 103 Views
-
GONE COASTAL at FOUNTAINHEAD CONDOMINIUMS - Accommodating up to four guests for a fun laid back beach vacation, Fountainhead Unit 2 offers the perfect two bedroom, two bathroom getaway for you and your family. Centrally located on Anna Maria Island, Fountainhead Unit 2 is near everything for an entertaining stay including gulf beaches, free trolley
Fountainhead 2 - Gone Coastal
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 13 Views
-
BG’s Bungalow is your quintessential “Key West style” home that is located on the beautiful North End of Anna Maria Island where guests can enjoy the world-renowned beaches that are just across the street! This home offers guests a true island-experience with its tall ceilings, beachy decor, and amount of outdoor space. This bedroom has 4 bedrooms,
BGs Bungalow
Home- 4
- 4
- Pool
- No Pets
- Sleeps 8
- 24 Views
-
Discover the revitalized charm of Coconuts Beach Resort 101, a newly remodeled ground-level condo located in the heart of Holmes Beach on Anna Maria Island. This one-bedroom, one-bathroom retreat has been given a complete makeover, offering a clean, modern aesthetic with inviting coastal touches. Comfortably accommodating up to four guests, this po
Coconuts 101
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 54 Views
-
Charming cottage-style condo w/ shared pool, Gulf views and easy beach access!<br /><br />Vacation in style with this charming cottage-style condo on Anna Maria Island. Featuring a shared pool, Gulf views from the balcony, and easy access to gorgeous beaches, this condo is perfect for a couple of friends or a romantic retreat. Wake up to the sun st
Palm Isle Village 3210
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 26 Views
-
“Summer Breeze” is one of the premier homes on the island. The perfect home for an Anna Maria Island getaway. With tropical landscaping, updated inside and out, and this rental home is stunning on all fronts. Elevated, high-end tropical décor, and pristine floors, “Summer Breeze” is love at first sight. Five large bedrooms, a spacious layout, this
Summer Breeze
Home- 5
- 4
- Pool
- Dogs Allowed
- Sleeps 14
- 31 Views
-
On Anna Maria Island nothing is far from the beach, and "Maria's Way" is no exception. Walk just a short distance, about two blocks north, to the island most secluded powder sand beaches at beautiful Bean Point https://www.islandreal.com/bean-point-vacation-rentals. Not only close to the beach, also enjoy nearby Pine Avenue boutiques, restaurants a
Marias Way
Home- 3
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 22 Views
-
This beautiful Holmes Beach get-away is sure to make your stay on Anna Maria Island a memorable one. “Water’s Edge 204S” is a beach side condo with views of the tropical garden are just outside your window as well as peeks of the beach and Gulf of Mexico. Unit 204S is updated, with a gorgeous kitchen, spacious living area, and a dining area that ca
Waters Edge 204S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 11 Views
-
Welcome to “Blue Water Escape” – Your Island Retreat in Holmes Beach!Experience laid-back island living just steps from the sugar-sand shores of Anna Maria Island at this inviting vacation home. “Blue Water Escape” is a bright, beachy getaway perfect for up to six guests, offering three bedrooms, two bathrooms, and everything you need for a relaxin
Blue Water Getaway
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 11 Views
-
Gulf View Cottage is a charming, recently renovated home with a rooftop deck offering sweeping views of the Gulf. Relax and enjoy the private, heated pool while experiencing the ultimate Florida vacation!As you arrive at Gulf View Cottage, you'll notice its unique shape, spacious driveway, and beautiful tropical plants in the front yard. Step insid
Gulf View Cottage
Home- 3
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 39 Views
-
Staying at Buena Vista unit 4 is a fun and memorable experience. Including comfortable furniture, smart televisions in all rooms with HBO and Showtime, and a custom chefs kitchen with induction stove as well as a double door wine fridge; vacationers love celebrating their stay in the spacious living room perfect for entertaining. The open floor pla
Buena Vista 4
Condominium- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 38 Views
-
Discover coastal living at its finest with this stunning 3-bedroom, 3-bathroom bayfront home located at “Royale View” 631 Key Royale Dr, Holmes Beach, FL. Newly remodeled and ideally situated directly on the water, this single-level retreat offers unparalleled access to ocean activities and breathtaking bay views.Perfect for both relaxation and en
Royale View
Home- 3
- 3
- Pool
- Dogs Allowed
- Sleeps 6
- 48 Views
