Holiday Rentals in Anna Maria Island

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Holiday Rentals in Anna Maria Island

Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, 157 reviews
"Two-story beachfront resort. Every room is pool side, and every second-floor room has a view of the beach! Great place to stay!"
The price is €793
includes taxes & fees
5 Jun - 6 Jun
Anna Maria Beach Resort
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, 21 reviews
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, 188 reviews
"Great property, it’s close to the beach, restaurants, checking in and out very easy (all done via text and phone). The beach across the street is beautiful. Definitely coming back."
The price is €422
includes taxes & fees
3 Jun - 4 Jun
Pelican Post at Anna Maria Island Inn
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Tradewinds Beach Resort
2.5 star property
9.2 out of 10, Wonderful, 353 reviews
"Friendly staff. Diane was very helpful."
The price is €397
includes taxes & fees
14 Jun - 15 Jun
Tradewinds Beach Resort
Queen's Gate Resort
2.5 star property
9.0 out of 10, Wonderful, 380 reviews
"The Location 100 steps to the beach ! Property manager Kathy and assistant manager Pete were amazing they attended to every need we had , gave us a tour of the property and followed up every day on how our stay was ."
Queen's Gate Resort
Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, 347 reviews
"Peaceful "
The price is €371
includes taxes & fees
9 Jun - 10 Jun
Haley's at The Anna Maria Island Inn
The Sailor Park
3.0 star property
3.2 out of 10, 15 reviews
"This was a very welcome get away. Absolutely beautiful views. The owner is great. I definitely will come back. "
The price is €167
includes taxes & fees
3 Jun - 4 Jun
The Sailor Park
Anna Maria Sunsets - studio
9.2 out of 10, Wonderful, 174 reviews
"Beautiful"
Anna Maria Sunsets - studio
Anna Maria Sunsets - studio
9.4 out of 10, Exceptional, 185 reviews
"Nice room, a little small but adequate, although an outside area for sitting (private) would have been nice. Excellent location across a busy street from a beautiful beach with a shady gazebo to sit in and next to a jet ski rental! Anna Maria Free Shuttle takes you up and down the island and runs every 20 minutes, with a stop very close by. Walking distance to the "Bridge Street" shopping and dining block!"
The price is €267
includes taxes & fees
30 Jun - 1 Jul
Anna Maria Sunsets - studio
Completely remodeled beach front condo with full ocean views, steps to the water
9.8 out of 10, Exceptional, 190 reviews
"This is a lovely modern condo with excellent furnishings. This was an effortless vacation."
The price is €516
includes taxes & fees
13 Jun - 14 Jun
Completely remodeled beach front condo with full ocean views, steps to the water
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
9.8 out of 10, Exceptional, 156 reviews
"PROPERTY WAS IN A PERFECT LOCATION ON THE ISLAND Had a fantastic week."
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
The Pink House Unit B: A Cozy Retreat Steps from the Beach
9.8 out of 10, Exceptional, 66 reviews
"The Pink House Unit B was one of the best units I have stayed using VRBO for years now. The pictures do it perfect justice. It’s a nice quaint space with a 1 min walk to beach. The unit is literally across the street from the beach which was quiet, not crowded at all. The only tiny drawback was the bathroom. The shower and toilet do need updates but don’t let that detour you one bit. Great place and location! I would rent again for sure!!!"
The Pink House Unit B: A Cozy Retreat Steps from the Beach
The Pink House Unit A: A Cozy Retreat Steps from the Beach
9.4 out of 10, Exceptional, 58 reviews
"house was perfect as we just needed a place to sleep since we were visiting friends who live on the island. as it turned out the house was close to the beach, shopping, bars and restaurants so it was a plus for us! plenty of room for the four of us"
The Pink House Unit A: A Cozy Retreat Steps from the Beach
Anna Maria Beach Condo 1/1
9.8 out of 10, Exceptional, 178 reviews
"Property was as advertised. Location was good and quiet. Close to ocean and walking distance to several reasonable restaurants"
The price is €317
includes taxes & fees
14 Jun - 15 Jun
Anna Maria Beach Condo 1/1
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
9.8 out of 10, Exceptional, 133 reviews
"Loved the convenience of the location. The manager was very helpful when needed"
The price is €383
includes taxes & fees
3 Jun - 4 Jun
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, 28 reviews
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
10.0 out of 10, Exceptional, 167 reviews
"We loved the location. Very walkable to the pier, beach, restaurants/shopping. Bungalow is tucked away with great privacy."
Naut 2 Shabby Bungalow 🤗 A sweet and cozy getaway on Pine Avenue!
Adorable luxury Resort Unit in a perfect location! Great Pool area!
9.6 out of 10, Exceptional, 49 reviews
"Nice unit, but a bit difficult without a washer and dryer in the unit and one can easily be put in in the closet of the main bedroom. We asked for more towels and were told they would be coming, but none were delivered. The kitchen was nicely equipped with what we needed and we liked the pool, outdoor patio, and proximity to the pier. Thank you for a lovely stay."
The price is €628
includes taxes & fees
3 Jun - 4 Jun
Adorable luxury Resort Unit in a perfect location! Great Pool area!
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
9.8 out of 10, Exceptional, 258 reviews
"Absolutely beautiful property & location was amazing!!! We had an absolutely wonderful time!! The house has a wonderful lanai and pool area that accommodates many people …. This home has a lot of steps that was the only downfall so if you have somebody in your party, that can’t handle steps. This wouldn’t be a good location for them but other than that everything was great."
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
9.8 out of 10, Exceptional, 100 reviews
"We enjoyed our stay at Bay - Canal Waterfront! We enjoyed the amenities - the pool is beautiful, large and in the sun all day but plenty of shady areas if you want that too. The kayaks were enjoyed as well and we did have some manatee sightings! We enjoyed the golf cart as well! The layout of the house is 2 separate areas with a full unit on top and on bottom. The only complaint we had which cannot be controlled by the owner is the smell of the muck that congregates at the end of the canal which...
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
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See all available properties in Anna Maria Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Anna Maria Island you may be interested in

Silver Surf Gulf Beach Resort
3.0 star property
9.4 out of 10, Exceptional, 1,005 reviews
"It was great! Close to many things!"
The price is €230
includes taxes & fees
16 Jun - 17 Jun
Silver Surf Gulf Beach Resort
Bali Hai Beachfront Resort and Spa
3.5 star property
8.6 out of 10, Excellent, 449 reviews
"The staff was amazing! Mike the bartender is great! The manager was so kind. Front desk staff super helpful. Great place. We loved it so much, we WILL be coming back!"
The price is €464
includes taxes & fees
9 Jun - 10 Jun
Bali Hai Beachfront Resort and Spa
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, 21 reviews
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Anna Maria Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anna Maria Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anna Maria Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria Island holiday rentals we have selected for you start as low as €141 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anna Maria Island rentals

At Expedia, we put the best Anna Maria Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Anna Maria Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anna Maria Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anna Maria Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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