- 100 properties returned
-
Sort by:
Random
- Name
- Beds
- Beds
- Sleeps
- Sleeps
- Random
- Price
-
LESS THAN A 5MIN WALK TO THE GULF BEACHES - Find the perfect Anna Maria Island vacation spot at “Starfish Beach Cottage 2”! This newly renovated duplex is comfortable, stylish and close to the beach too! When you visit “Starfish Beach Cottage 2” you’ll find everything you’ll need for up to four guests. Inside this Holmes Beach rental you’ll find a
Starfish Beach 2
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 40 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
- 36 Views
-
Newly Updated - New bathrooms and updates completed in February of 2023!! Four minutes from the beach, located in the heart of Holmes Beach, and a private oasis on Anna Maria Island. All this and more makes “Forget Me Knot” the ideal place to stay during your island vacation. From the secluded and private placement to its closeness to the beach as
Forget Me Knot
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 22 Views
-
Experience Island Living at Waters Edge 208S, an exquisite, newly remodeled condo located just a short stroll from the serene shores of Anna Maria Island. Whether you're drawn to the beach for sunbathing, water sports, or peaceful relaxation, this charming property has it all. With easy beach access, a shared heated pool, and local shops and restau
Waters Edge 208S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 42 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
- 1377 Views
-
"Flip Flop Oasis" Two Single Family Homes with Adjoining Yards and TWO Heated PoolsFirst Home 201 57th Street "Flip Flop Inn" If you are searching for luxury on your Island vacation, this home is your dream come true. Tucked away on a quiet street on Anna Maria Island, this Mediterranean-style Townhouse is your perfect family vacation destination.T
Flip Flop Oasis
Multi-Family- 6
- 6
- Pool
- No Pets
- Sleeps 12
- 40 Views
-
“Palm Isle 3211” is the perfect Anna Maria Island beach rental for a cozy couple’s getaway, or even a casual vacation for up to four guests. This one bedroom villa beach rental offers a premium location near beaches, shopping and dining. Enjoy a well-appointed unit with nice updates and a laid back feel.<br /><br /> When you visit “Palm Isle 3211”
Palm Isle Village 3211
Condominium- 1
- 1 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 4
- 33 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
- 26 Views
-
This recently built single-family home is situated on a serene and picturesque street, just 6 houses away (ONLY STEPS) from the beach access path!On the ground floor, the home features a 1 car garage and provides access to the stunning pool and patio areas within the beautifully landscaped backyard. The residence boasts a dazzling, spacious heated
Sea Glass on Park
Home- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 66 Views
-
When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Piece of Paradise”. This fun four bedroom, three bathroom Holmes Beach vacation rental spaciously sleeps up to 8 guests in comfort and style. After spending a week at this fabulous Holmes Beach vacation rental home within walking di
Tinas Piece of Paradise
Home- 4
- 3
- Pool
- No Pets
- Sleeps 8
- 13 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- 5
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 10
- 35 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
- 33 Views
