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
Welcome to “On the Rocks”! This professionally designed nautical themed home hosts 8 bedrooms and 8.5 bathrooms, plenty of space for large families or friends. This property has an elevator and is also pet-friendly. Bring your boat and fishing gear because On the Rocks is a waterfront home ...
Property Type
Anna Maria Island House
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About this property
Manatee Lookout is a charming 3 bedroom/3 bath home with a 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 ...
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!!!
Key Amenities
About this property
Dans Florida Condos Sea Dream, located within Runaway Bay, a lovely private community on beautiful grounds with private beach access to the Gulf of Mexico.The highlight of our community is the largest heated salt water pool on the island! The condo grounds highlight tennis/pickleball courts, bocce ...
Property Type
Anna Maria Island Apartment
This is the first time we stayed at Dans Florida Condos. The condos were right across the street from the private beach access, and I could not have asked for a cleaner unit. Pictures tell the whole story. ...
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 ...
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 MADE AFTER April 29, 2024! All Drivers must be over the age of 21. Drivers must provide valid US Driver's License and US Vehicle InsuranceSurfer's Dream boasts 4 bedrooms, 6 full bathrooms, and 1 half bath, and is also pet-friendly! This ...
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 ...
4 BR | 3 BA | Sleeps 8 | Quick View
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About this property
303 68th St, Holmes Beach 34217 VRC -You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made ...
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 | 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 ...
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
Key Amenities
About this property
Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath duplex is located on the north end of desirable Holmes Beach. This home offers all the comforts of home and is just steps to the beautiful white sandy beach. The kitchen is fully equipped ...
Property Type
Anna Maria Island House
Great location in middle of Ana Marie Island; close to beach, not to far to shopping and restaurants.Rum Dog is a clean two bedroom pet friendly unit with wonderful deck for eating and socializingRental ...
3 BR | 3.5 BA | Sleeps 6 | Quick View
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About this property
306 (A) Clark St - Holmes Beach - FL 34217 VRCYou may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations ...
Property Type
Anna Maria Island Townhome
This was our perfect getaway. The house is beautifully decorated inspired by the blue glistening water and white sandy beaches of Ana Maria Island. The kitchen was fully equipped with everything we needed ...
6 BR | 6.5 BA | Sleeps 12 | Quick View
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About this property
401 42nd Street Holmes Beach, FL 34217 VRC Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, ...
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 ...
4 BR | 3 BA | Sleeps 8 | Quick View
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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 ...
2 BR | 2 BA | Sleeps 6 | Quick View
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About this property
Dreaming of an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Step outside your door and find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay on site ...
Property Type
Anna Maria Island Condo
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 ...
5 BR | 6.5 BA | Sleeps 8 | Quick View
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About this property
Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat for your whole family. Situated close to the beach, shops, and restaurants, this property is an ideal choice. Just a brief stroll away from the beach, the house boasts a pool and hot ...
Property Type
Anna Maria Island House
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 ...
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
210 65th Street Holmes Beach, FL 34216 VRC Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, ...
Property Type
Anna Maria Island Bungalow
Location was good with only a short walk to the beach and in a quiet location. House was clean and there was plenty of room for the group. Lots of pool and beach toys for us and the kids. The pool needed ...
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
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
Get ready to be swept off your feet by the charm and luxury of Winding Waves, your dream vacation spot right on the beautiful Anna Maria Island. This dazzling nine-bedroom, eight-and-a-half bathroom beachfront home is all about fun in the sun and upscale relaxation!Splash and Play Outdoors: Dive ...
Property Type
Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
411 79th Street Holmes Beach, Fl 34217 VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations ...
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 ...
Key Amenities
About this property
VRC19 5th Ave Holmes Beach, FL 34217 You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on ...
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.
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
Compass Rose, a captivating residence offering deluxe amenities including a lazy-river-style pool with a hot tub, a game room, an elevator and a rooftop deck boasting amazing views of the Gulf of Mexico. This 9 bedroom, 8.5 bathroom, pet-friendly abode is an ideal beach retreat suitable for multiple families ...
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.
Key Amenities
About this property
Welcome to Zen Gardens on beautiful AMI. BIG NEWS: a brand new, full sized pool and spa was installed and is ready for your use. Zen Gardens is located just north of Pine Ave - and 1 house from the beach - in the City of Anna Maria. This property offers a beachy bohemian vibe and has all you need for ...
Property Type
Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Distance to beach: 0.1 miles to Tampa Bay
Key Amenities
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
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 ...
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 You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund ...
Property Type
Anna Maria Island Townhome
Outside patio was perfect! The pool and hot tub were great. Living room area was small but comfortable.
Key Amenities
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 | 3.5 BA | Sleeps 8 | Quick View
Distance to beach: 0.1 miles to Bean Point
Key Amenities
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
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
202 81 st Street - Holmes Beach - Fl 34217 VRC Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that ...
Property Type
Anna Maria Island Townhome
We enjoyed our stay. The access to the beach and other amenities was perfect for our family. The rental was very clean and well kept. Most everything you needed for the stay was available. The pool was ...
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. ...
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
The Salty Mermaid Team is excited to introduce our newest property, The Haven Unit 1 and Unit 2!*This property requires a 7-night minimum stay. Arrival and departure days must fall on a Saturday*When booking this listing, you will be reserving both Units at this Duplex.Haverkos on Holmes- ...
Property Type
Anna Maria Island House
5 BR | 5.5 BA | Sleeps 8 | Quick View
Key Amenities
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 ...
4 BR | 6.5 BA | Sleeps 8 | Quick View
Key Amenities
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.
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 with an elevator residence is ideally situated. Just steps away from the beach and within walking distance of shopping and restaurants, you'll have ...
Property Type
Anna Maria Island House
Key Amenities
About this property
Welcome to “Pineapple Cottage” – a beautifully updated ground level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants and fun on Pine Avenue. This charming cottage has been professionally decorated and offers all the luxuries you will ...
Property Type
Anna Maria Island House
This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay ...
Key Amenities
About this property
Dans Florida Condos Sea Esta, located within Runaway Bay, a lovely private community on beautiful grounds with private beach access to the Gulf of Mexico.The highlight of our community is the largest heated salt water pool on the island! The condo grounds highlight tennis/pickleball courts, bocce ...
Property Type
Anna Maria Island Apartment
The location is great, right across street from beach. Trolly stop nearby to ride around the beach and get off at other stops for free. Places to eat within walking distance. Nice pool and tennis courts. ...
Key Amenities
About this property
35 Steps to the Sea at Runaway Bay 112 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
This was a very nice condo. Clean and well kept. Very close to the beach and to the pool. Location was everything we wanted. Walking distance to restaurants and the heart of town. Great food, great people. ...
5 BR | 4.5 BA | Sleeps 10 | Quick View
Key Amenities
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
5 BR | 5 BA | Sleeps 14 | Quick View
Distance to beach: 0.1 miles to Bayside Beach
Key Amenities
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
Key Amenities
About this property
In the heart of Holmes Beach on Anna Maria Island rests this charming pet-friendly home just steps to the beaches. Misty Beach is a charming coastal home with a flamingo-shaded exterior, quickly moving you onto island time. The interior showcases island artwork, creating a welcoming and calming environment. ...
Property Type
Anna Maria Island House
Key Amenities
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
1 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Vacations can be exciting and so overwhelming. Don’t worry, we’re here to help. Pack your bags and get ready to enjoy our beautiful island. This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will ...
Property Type
Anna Maria Island Condo
Key Amenities
About this property
2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.
Property Type
Anna Maria Island Apartment
We had a great time. Kathy and Peter were amazing hosts who took care of our every need. We will be back again.
4 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Longing for an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay ...
Property Type
Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
VRC Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on or less than ...
Property Type
Anna Maria Island House
