- 93 properties returned
-
Sort by:
Random
- Name
- Beds
- Beds
- Sleeps
- Sleeps
- Random
- Price
-
Relax and unwind in the luxurious Anna Maria Island vacation rental home “Beach Pearl”. This five star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just a block and a half from the powder sand beaches of Anna Maria City, “Beach Pearl” is the quintessential Anna Maria Island
Beach Pearl
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 36 Views
-
*Please Note: Exterior painting and roofing projects are scheduled between Sept 22–Dec 31, 2025. Work may cause noise or limited access to decks. Schedule may vary due to weather.*With stunning direct gulf front views, the stylish “Water's Edge 209S” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 4 guests this 2 be
Waters Edge 209S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 15 Views
-
Discover your perfect island escape at Coconuts Beach Resort Unit 108! A completely renovated, ground-floor condo situated directly on the shores of the Gulf in the heart of Holmes Beach on Anna Maria Island. This modern, one-bedroom, one-bath vacation rental offers a fresh and inviting coastal retreat, just steps from the sand.Thoughtfully redesig
Coconuts 108
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 19 Views
-
Welcome to Moon Shadow South, a beautifully designed coastal retreat offering 3 bedrooms, 2 bathrooms, and breathtaking views of Tampa Bay and Passage Key from the top-level primary suite. This inviting island home is perfectly situated just steps from bay beach access and a short walk to Bayfront Park and Bean Point’s renowned shoreline.Inside, th
Moon Shadow South
Home- 3
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 40 Views
-
Welcome to Jacaranda Beach House, a beautifully refreshed vacation retreat tucked away in Anna Maria Island’s desirable North End. Just three homes from the sugar-white sands and a short walk to the island’s northernmost point, this home places you moments from the natural beauty of Bean Point and the charm of Pine Avenue’s boutiques and eateries.D
Jacaranda Beach House
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 32 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
-
“Salty Sea Life” is a home away from home, newly remodeled and situated on a canal. This 3-bedroom 2 bath Bradenton home has both the space and accommodations for up to six people. Take full advantage of that space with your family and loved ones, as the living area is perfect for lounging and get togethers. Relax on the inviting sofas and take in
Salty Sea Life
Home- 3
- 2
- No Pets
- Sleeps 6
- 16 Views
-
Fun and tastefully decorated recently remodeled, “Aquarius” is the ideal place for a fabulous Anna Maria Island vacation getaway for up to eight guests. Situated just a short walk from beautiful gulf beaches, when you visit this vibrant vacation rental you’ll leave with memories that last a lifetime.Offering four bedrooms and two and a half bathroo
Aquarius
Home- 4
- 3
- Pool
- Dogs Allowed
- Sleeps 8
- 20 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
-
*Current construction on the premises, may hear construction noise 7am-7pm*The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Anna Maria Island. We are always very proud to recommend to our vacationers, and no one can say it isn't a special place to spend quality time with friends and family. With so ma
Palm Isle Village 3203 - Pink Flamingo
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 16 Views
-
Ready to find your piece of island paradise? Look no further than “Wave N’ Sea”. This beautiful, sunny Anna Maria home is a spacious three-bedroom two-bathroom rental that can accommodate up to six guests. With a new, and private, heated pool, an oversized yard with tropical landscaping, and less that two blocks from the beach, “Wave N’ Sea” is tru
Wave N Sea
Home- 3
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 24 Views
