Anna Maria Island Vacation Rentals

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Vacation Rentals in Anna Maria Island

Beach nearby, sun loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (233)
"This adorable little cottage is perfectly located! We could walk to restaurants, the beach and the free trolley. It was quiet and serene! The house was so clean, beautifully decorated and fully stocked! Cindy was a fantastic host! Thank you for helping make our reunion for our 35th anniversary as friends such a special experience. We will definitely be back!"
Charming cottage in quiet area, close to beach & bay.
Beach
Anna Maria Beach Condo 1/1
10.0 out of 10, Exceptional, (175)
"Great place to stay for families with small children. Short, easy walk to beach and restaurants. Very clean and spacious living area. Very relaxing condo! Host was very responsive. Can’t wait to come back and/or check out other Condos by host!"
The price is CA $191
CA $453 total
includes taxes & fees
Jun 14 - Jun 15
Anna Maria Beach Condo 1/1
On the beach
Beachside Bliss Steps to the Sand! 1BD1 Bath Condo
10.0 out of 10, Exceptional, (2)
"It was perfect for us."
The price is CA $217
CA $706 total
includes taxes & fees
May 22 - May 23
Beachside Bliss Steps to the Sand! 1BD1 Bath Condo
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Property grounds
Anna Maria Guest House 401- 3 bedrooms in the middle of everything
10.0 out of 10, Exceptional, (8)
"Very roomy rental with multiple amenities right in the heart of it all!"
Anna Maria Guest House 401- 3 bedrooms in the middle of everything
View from property
The Pink House Unit B: A Cozy Retreat Steps from the Beach
9.8 out of 10, Exceptional, (65)
"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
On the beach, sun loungers, beach towels
Completely remodeled beach front condo with full ocean views, steps to the water
9.8 out of 10, Exceptional, (190)
"This is a lovely modern condo with excellent furnishings. This was an effortless vacation."
The price is CA $407
CA $680 total
includes taxes & fees
May 27 - May 28
Completely remodeled beach front condo with full ocean views, steps to the water
Beach nearby, sun loungers, beach towels
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
9.8 out of 10, Exceptional, (131)
"Property location was great. Clean and spacious. Parking space was a plus for us. We stayed for a short stay but would return and stay here. Communication w/ PM was easy and accessible."
The price is CA $240
CA $517 total
includes taxes & fees
May 23 - May 24
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
Outdoor pool, a heated pool
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
9.8 out of 10, Exceptional, (156)
"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
Beach nearby
Villa by the Sea #3; Heated Pool, Walk to Beach & Shops- Perfect Location!
9.8 out of 10, Exceptional, (58)
"We had a wonderful week at Villa By The Sea #3! You can walk to the beach and lots ofshops and restaurants. Condo is small but nice for a couple."
Villa by the Sea #3; Heated Pool, Walk to Beach & Shops- Perfect Location!
Beach nearby, sun loungers, beach towels
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
9.8 out of 10, Exceptional, (257)
"I rented this entire house for my sons wedding on Anna Maria Island. Giving 5 stars for this place feels like an injustice. The location is perfect-a short walk to watch the sunrise on the bay or the sunset from the beach. Plenty of parking, but who needs a car when there’s a free trolley right out your door to take you anywhere on the island. No need to pack for the beach. This property provides anything you would ever need, from chairs to towels to beach toys, and a wagon to load it all in....
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
A heated pool
Bay -Canal Waterfront! Tiki Bar 5BR, 5BA Heated Pool 2 Kitchens, Golf Cart
9.8 out of 10, Exceptional, (100)
"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
Interior
Family Beachfront condo boasting 180-degree views. Steps from sand!
9.8 out of 10, Exceptional, (169)
"So close to the beach and walkable to the restaurants and shops."
Family Beachfront condo boasting 180-degree views. Steps from sand!
Beach nearby, sun loungers, beach towels
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
9.8 out of 10, Exceptional, (64)
"This was our third stay at Boathouse Cottage and it never disappoints. Stocked with everything you need for your stay. Short stroll to the beach. We love the private pool. The pool is in the sun all day. A lot of the rentals have shaded pool areas which is not what I want coming from the north! We have already booked again for next year, we can’t wait!"
Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay
A heated pool
Perfectly Located Home with Pool and Spa
9.6 out of 10, Exceptional, (20)
"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
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (157)
"The location and views were incredible! It was so great being right on the beach and it was easy to walk everywhere. Unfortunately the house is a little tired, the refrigerator should be replaced as the door doesn’t close well, the shower head in the primary bathroom should be replaced and the pillows/mattresses need updating. Again, the location and views are stunning and we had the best time playing on the beach and in the water all day, but for the expensive cost per night, we were...
The price is CA $476
CA $1,118 total
includes taxes & fees
Jun 12 - Jun 13
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Property grounds
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, (28)
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
On the beach, white sand, beach towels
Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (155)
"From check in to check out our new experience was excellent. We wanted quiet and relaxed and this was the perfect place. Right on the white sand beach with resort lounge chairs. Everyone was friendly and helpful in providing us tips on places to go for activities and food. The entire resort was incredibly clean and well maintained. Will definitely return to this resort!! "
The price is CA $783
CA $982 total
includes taxes & fees
May 22 - May 23
Anna Maria Beach Resort
Sun loungers, beach towels
Anna Maria Sunsets - studio
9.4 out of 10, Exceptional, (185)
"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 CA $109
CA $266 total
includes taxes & fees
Jun 7 - Jun 8
Anna Maria Sunsets - studio
Smart TV
The Pink House Unit A: A Cozy Retreat Steps from the Beach
9.4 out of 10, Exceptional, (57)
"Clean cute house with great location."
The Pink House Unit A: A Cozy Retreat Steps from the Beach
Fridge, microwave, oven, stovetop
Near Bean Point!! Short stays available! Heated Pool
9.4 out of 10, Exceptional, (33)
"Property was very comfortable and clean - we enjoyed our stay even thought the pool was closed for resurfacing they gave us access to a beach resort with a pool - a great compromise. Had some electrical issues that were corrected very quickly at no inconvenience to us."
Near Bean Point!! Short stays available! Heated Pool
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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

A heated pool
Perfectly Located Home with Pool and Spa
9.6 out of 10, Exceptional, (20)
"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
Private beach nearby, beach umbrellas, beach towels, beach massages
Silver Surf Gulf Beach Resort
3.0 star property
9.4 out of 10, Exceptional, (1003)
"Right across the street from the beach, super easy access with free umbrellas and chairs.Free trolley stop at the hotel. Noah was super friendly and helpful. Very nice rooms with fridge and microwave. Breakfast was light but plentiful."
The price is CA $303
CA $340 total
includes taxes & fees
May 27 - May 28
Silver Surf Gulf Beach Resort
2 outdoor pools, sun loungers
Tortuga Inn Beach Resort
2.5 star property
9.2 out of 10, Wonderful, (632)
"The property was convenient to the shops, restaurants, grocery store and beach! "
Tortuga Inn Beach Resort
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Anna Maria Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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