3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 0.1 miles to 30 seconds to your left
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About this property
This newly redesigned elevated 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and it's stunningly ...
Property Type
Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Distance to beach: 0.1 miles to Bean Point
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About this property
Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling luxury home named for its spectacular porches and outdoor space.*Features include** Ultimate luxury vacation home with elevator^ * Private heated pool and backyard oasis * Poolside lounge, ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
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About this property
Relax with the whole family at this peaceful place to stay.Endless Summer is two bedroom, two bath condo located on Anna Maria Island. Specifically, located in Runaway Bay on Bradenton Beach.We have beach wagon. umbrella, chairs and cooler for your use. This unit is ground level, no stairs!Endless ...
Property Type
Anna Maria Island Condo
My husband and I recently stayed at this condo while visiting family and friends. This was the perfect condo and perfect location for us. Unfortunately, the pool was down for repairs of some sort but we ...
5 BR | 5 BA | Sleeps 14 | Quick View
Distance to beach: 0.1 miles to Bayside Beach
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About this property
Just updated 2020, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep many with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for smaller ...
Property Type
Anna Maria Island House
6 BR | 5.5 BA | Sleeps 14 | Quick View
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About this property
ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access!This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...
Property Type
Anna Maria Island House
Beach house was so nice, clean and beautiful. We had plenty of room for our party of eleven. Very short walk to the beach. Loved the pool area. Would stay at Oceanview again. Weldon checked on us and made ...
5 BR | 2 BA | Sleeps 10 | Quick View
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About this property
One of the highest rated vacation homes on Anna Maria Island with more than 150 five-star ratings from Airbnb/VRBO!Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated ...
Property Type
Anna Maria Island House
We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...
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About this property
Come experience Unit 204 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated pool and ...
Property Type
Anna Maria Island Condo
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About this property
Condo-cottage with Old Florida charm..... Welcome to paradise.....This updated cottage is within a small resort, just steps from a beautiful private gulf beach. Drive into the Tradewinds Resort, and you will find quaint, pastel colored cottages on both sides of you hidden behind lush tropical foliage. ...
Property Type
Anna Maria Island Cottage
We gave this 5 stars but my husband wanted to do 4 1/2. The reason he was disappointed that the dock and pier are set up for fishing, but the staff knew nothing about it. Also, seems like it would be smart ...
4 BR | 4 BA | Sleeps 8 | Quick View
Distance to beach: 0.1 miles to Tampa Bay
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About this property
Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool, spa and mini golf.*Features include** Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Standalone Hot Tub * Gas grill ...
Property Type
Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the ...
Property Type
Anna Maria Island House
What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...
3 BR | 3 BA | Sleeps 6 | Quick View
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About this property
Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside ...
Property Type
Anna Maria Island House
5 BR | 4.5 BA | Sleeps 10 | Quick View
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About this property
This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island!As you step through the front door, you enter a bright and ...
Property Type
Anna Maria Island House
3 BR | 3 BA | Sleeps 6 | Quick View
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About this property
Welcome to Gone Coastal 3! This quaint three bedroom, two bathrooms plus a half bath vacation home is located just a short walk from Anna Maria Island’s sugar white sands and crystal clear waters! Beach towels, six beach chairs, and a beach wagon are provided to ensure your days spent in the sun ...
Property Type
Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just steps away to the bay beach access located directly across the street; walking distance to the Rod and Reel Pier, Bay Front Park and the popular white sandy beach of Bean ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Welcome to SURF’S UP! Located one block from the sugary white sand beaches on the desirable north end of the Anna Maria. SURF’S UP is a 2 bedroom, 2 bath cottage that has been completely and lovingly renovated from top to bottom and is gorgeously decorated, meticulously maintained and ready ...
Property Type
Anna Maria Island Cottage
Key Amenities
About this property
My wood-frame beach cottage was built in 1936, and was originally part of 6-8 cottages and a lodge house. It is the only surviving cottage, many having been taken by hurricanes. (Forward of the cottage’s beach, a street and an entire city block of the old subdivision are submerged beneath the ...
Property Type
Anna Maria Island Cottage
So close to the water for someone with gait issues. We always enjoy our stay here. So close to restaurants and beach. Best of both worlds
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About this property
Pine Avenue HideAway is a secluded Beach Bungalow tucked away on Historic Pine Avenue on Anna Maria's North End. Conveniently located in the heart of it all, and just a short stroll to the beach, restaurants, boutiques, Anna Maria City Pier and a trolley stop to explore Anna Maria the islanders way!. ...
Property Type
Anna Maria Island Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
*** SPECIAL *** Book a 14 day stay and ONLY pay for 12Buckeye Haven s situated in one of the sought after community of Playa Encantada! Come enjoy this tropical beach front community on the white sandy beaches of Anna Maria Island! This popular destination is sure to please beach goers, as well as ...
Property Type
Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
North End Escape is a 2,300 sq. ft. Newly Built 3 bedroom 2 ½ bathroom Custom Home featuring a 400 sq. ft. Rooftop Covered Gazebo; 750 sq. ft. of Covered Outdoor Living Area with Travertine flooring and a Heated Pool.This spacious home has wide plank hardwood flooring throughout; open concept ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach.Inside it has a split plan with a king sized bedroom and a second bedroom ...
Property Type
Anna Maria Island House
Key Amenities
About this property
It is almost always summer on Anna Maria! Availability is updated frequently, so please check our calendar often. There are a smattering of weeks here and there still available!Peacock Place is a sprawling old-Florida style home with 4 bedrooms, 2 bathrooms, and plenty of space. It is ideal for ...
Property Type
Anna Maria Island House
My husband and I stayed in the Peacock house 2 years in a row and loved it. Denise is an excellent host and the house was amazingly roomy. The kitchen was outfitted with every item you could imagine. ...
1 BR | 1 BA | Sleeps 4 | Quick View
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About this property
When it's time to run away— to escape to a tropical island oasis where the bright sun is shining and the gentle sea breezes are endless— then it's time to book a stay at Runaway Bay 117. This cozy coastal hideaway is tucked within one of the most exclusive Anna Maria Island communities ...
Property Type
Anna Maria Island Condo
We've been on Ana Maria Island before; it's a lovely area. This was a great location for us and the management was very prompt and considerate whenever we contacted them. Thank you so much!
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About this property
Manatee Lookout is a charming 3 bedroom/3 bath home with private heated pool located on the sought after north end of Anna Maria Island. This home has everything you need for the perfect vacation and is only a short walk to the white sandy beaches. Upon entry, you have the living room where you can relax ...
Property Type
Anna Maria Island House
We enjoyed our trip to Anna Maria. Very quant, quiet beach. Beautiful clear water and amazing sunsets. Can’t wait to go back!!!
9 BR | 10 BA | Sleeps 18 | Quick View
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About this property
Gather your family and friends and head to Swanky Bubbles! Swanky Bubbles can accommodate 18 people! This exquisite 9-bedroom, 11-bathroom, pet-friendly residence is ideally situated. Just steps away from the beach and within walking distance of shopping and restaurants, you'll have ample entertainment ...
Property Type
Anna Maria Island House
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About this property
LimeFish is a luxurious newly remodeled 3 bedroom (1 king-sized, 1 queen-sized, and a bunk room)/3 bathroom single level home right on the sands of Anna Maria Island. Additional sleeping accommodations can be added with the sleeper sofa in the living room. It is a perfect destination for a trip with family ...
Property Type
Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
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About this property
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceThis gorgeous, custom-built, professionally designed, private home is a 4 bedroom/6.5 ...
Property Type
Anna Maria Island House
Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.
Key Amenities
About this property
Large 4 bedroom/2 bathroom Ocean view home with screened porches in the front and back. Elevator to the main level. Beach is right across the street. Bikes, Paddle Boards and a golf cart included. We are pet friendly! Pre-approved pet's , a signed pet agreement and pet fee paid in full will be needed. ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the grand total. 7106 Marina Dr - Holmes ...
Property Type
Anna Maria Island House
Key Amenities
About this property
35 Steps to the Beach at Runaway Bay 104 is a 1 bedroom/1 bath, ground floor condo that can sleep 4. Featuring the largest heated pool on the island, private beach access, gym, and an array of amazing amenities, this ground-floor condo is your perfect home base on the Gulf Coast. The fully-equipped kitchen ...
Property Type
Anna Maria Island Condo
First time to Anna Maria Island and we really enjoyed it. We usually stay in Siesta Key but I think we found a new favorite area. The pool was very nice at this property and the beach is right across ...
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About this property
Discover Serendipity: Your Pet-Friendly Beachfront Haven on Anna Maria Island Beachfront Bliss Awaits You Indulge in the enchantment of beachfront bliss at Serendipity, an exceptional 4-bedroom home perfectly positioned on the coveted North End of Anna Maria Island. This tranquil escape beckons you to ...
Property Type
Anna Maria Island House
5 BR | 3 BA | Sleeps 10 | Quick View
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About this property
Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200 steps) ...
Property Type
Anna Maria Island House
Love, Love, Love this beach house. I had reserved it a year in advance and was concerned about coming here during a pandemic but as soon as I arrived I was so happy and relieved to be here. The first ...
Key Amenities
About this property
Compass Rose, a captivating residence offering deluxe amenities including a lazy-river-style pool with a hot tub, a game room, and a rooftop deck boasting amazing views of the Gulf of Mexico. Situated just a brief stroll from the powdery white sands of the Gulf, this 9 bedroom, 8.5 bathroom, pet-friendly ...
Property Type
Anna Maria Island House
Very clean and comfortable. Easy walk to everything you need and want to do. I would stay there again and highly recommend.
4 BR | 4 BA | Sleeps 8 | Quick View
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About this property
Mintfish is a tropical hideaway that blends high-end decor with natural beauty. This 4 bedroom, 4 bath ground-level luxury vacation home has recently been remodeled to combine natural and sustainable materials with decadent living. The single-floor layout makes the home easily accessible to people of ...
Property Type
Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
302 60th Street Holmes Beach, FL 34217 VRC At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for your next Anna Maria Island getaway! Two short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish ...
Property Type
Anna Maria Island Townhome
My husband and I had the best time at the home we rented on Anna Maria Island. It was spacious and we had far more room than we needed for just the two of us. When we arrived, everything was clean and easy ...
Key Amenities
About this property
VRC19 5th Ave Holmes Beach, FL 34217 Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the grand total. We do our ...
Property Type
Anna Maria Island House
House was very comfortable. Everything was as advertised. Pool heater was not working when we checked in. They offered us the use of the pool next door. It was very kind and made our trip perfect.
Key Amenities
About this property
Island Dream is a recently updated custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 3 bedrooms/2 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the brand new (2018) luxurious heated pool and spa, ...
Property Type
Anna Maria Island House
This was my family's first vacation to Anna Maria island. The house was beautiful and in a great location, convenient to all the hot-spots! The lay-out of the house was great, master bed and queen beds ...
8 BR | 6.5 BA | Sleeps 18 | Quick View
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About this property
Paradise Beach lives up to its name! Nestled directly on the pristine soft white sands of Bradenton Beach, this remarkable property boasts 8 bedrooms, 6.5 bathrooms, and is pet-friendly. Complete with an elevator, it comfortably accommodates up to 18 guests. Bring your family and friends along to experience ...
Property Type
Anna Maria Island House
Truly an amazing resort and we loved staying in Sunset Seacret! Our family enjoyed every minute! We looked hard to find a beautiful, safe, clean, beachy condo with 2 king beds, as we were vacationing with ...
5 BR | 5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Beach Front/Heated Pool/Hot Tub/ 4 bedroom plus den North End of Anna Maria Island. Professionally decorated and finished with all King Beds and En-Suite Bathrooms. Chef's Kitchen with a 48inch gas range. Wine Cooler on two levels and a private covered porch to enjoy the sunsets on the upper levels. ...
Property Type
Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
303 68th St, Holmes Beach 34217 VRC - Book with confidence Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the ...
Property Type
Anna Maria Island House
This is a great house in a fantastic location. The close beach access is very convenient. There are 6 complimentary high quality beach chairs that came in very handy. There is even a handy beach wagon ...
5 BR | 5.5 BA | Sleeps 8 | Quick View
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About this property
Come stay at From Dusk 'Til Dune! This home is a recently built beach residence offering rooftop water views just one block away from the Gulf of Mexico beaches. This 5 bedroom, 5.5 bathroom, pet-friendly vacation haven is brimming with amenities. Its stunning backyard features a private pool, hot ...
Property Type
Anna Maria Island House
The condo was only surpassed by the view, which included a nightly explosion of sunset glory over the sound. If one wanted to be closer to the sun from the beach, the club directly on the gulf was only ...
6 BR | 6.5 BA | Sleeps 12 | Quick View
Key Amenities
About this property
401 42nd Street Holmes Beach, FL 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% ...
Property Type
Anna Maria Island House
We rented this home for time with our kids and grandkids. It worked great! The rooms were spacious and it was great that every room had a bathroom. We had no issues. The kitchen was well stocked. The backyard ...
Key Amenities
About this property
Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3.5 bathrooms. There is also a den where the kids can hang out with a TV and sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria Island vacation! ...
Property Type
Anna Maria Island House
This house was nice, clean and well stocked. The furniture was a bit worn but very comfortable. The yard is small but nicely landscaped and the pool was large enough for our family. The walk to the beach ...
Key Amenities
About this property
320 64th Street - Holmes Beach - FL - 34217 VRC Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With Backyard Oasis BOOK WITH CONFIDENCE Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations ...
Property Type
Anna Maria Island Townhome
Perfect place to stay , no problems at all !! Backyard with heated pool and heated jacuzzi was a perfect place to relax !!
4 BR | 4.5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive ...
Property Type
Anna Maria Island House
The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally ...
3 BR | 2.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
411 79th Street Holmes Beach, Fl 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% ...
Property Type
Anna Maria Island House
We really enjoyed this vacation rental home. Excellent location with close proximity to the beach and restaurants. Also, house located on a quiet street. Amenities were great including the pool and the ...
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
VRC 21 Holmes Blvd Holmes Beach, FL 34217 At 4 bedrooms and 3 full bathrooms, this is a great option for one or two families to stay at. A few short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Isle is ...
Property Type
Anna Maria Island Bungalow
The home was absolutely wonderful with everything we needed to make our weeklong vacation a success! Everything was clean and well kept. The beds were comfortable and the best part was the pool and pool ...
4 BR | 4.5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
128 49th St Holmes Beach VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the grand ...
Property Type
Anna Maria Island House
We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its ...
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or take the golf cart (included) to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king ...
Property Type
Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Escape to Your Exclusive Tropical Retreat!Indulge in the privacy of your own backyard oasis, complete with a sprawling pool and a dedicated Beach Volleyball Court. Open the back gate and find yourself steps away from the pristine Gulf Beaches. This ground-floor haven offers unparalleled convenience, ...
Property Type
Anna Maria Island House
Key Amenities
About this property
Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell searches out your back door. All bedrooms are King Bed en-suite. Located on the North End of Anna Maria Island. Gas BBQ on the lower deck. TV are located in all bedrooms. Plenty of space ...
Property Type
Anna Maria Island House
