Vacation Rentals & Beach Rentals in Anna Maria Island

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24 beach rentals

5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 24 minutes

Match: Private fishing lake or river

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Price per night from

$399

Runaway Bay, Anna Maria Island, ON THE BAY!

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful View!!” My husband and I had a relaxing stay at this condo and it was very well equipped. Saw dolphins most everyday from the lanai and beautiful sunrises! The owners daughter responded quickly to our questions. Would definitely return:)

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Price per night from

$246

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 55 minutes

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Price per night from

$101

C-viewFlorida, Canal/Dock/Heated Pool/Near Gulf - A Hidden Gem

Anna Maria house

5 bedrooms / 4 bathrooms / sleeps 10

“Great Beach Vacation Spot” A really outstanding vacation house. The house is roomy, up-to-date in every way, and clean beyond all means. It has everything you need if you want to cook and if not you are very close to great resturants. You are a short hop to a beautiful beach. But you also have your own swimming pool and dock-bring your boats or whatever. The place was extremely clean upon arrival and was easy to find. Just a great place for a vacation.

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Price per night from

$492

Great rentals within 20 miles that match your search

Siesta Key Oceanfront on Gulf with western sunsets, 1250 sq ft Townhome

Siesta Key villa

2 bedrooms / 3 bathrooms / sleeps 4

“Absolutely Perfect---one Kodak sunset after another” This townhome was gorgeous! We totally enjoyed our 3 week stay and hated to leave. Kelley (owner) could have not been more helpful. We fished off the dock and enjoyed watching the birds fish then dry their wings. Town is a short, enjoyable jaunt. Just a few blocks further are the most gorgeous beaches with sand like flour! If you are adventureous, walk to Point of Rocks at beach access 13 for the best shelling ever (only at very low tide)!!! We would come back in a heartbeat. The views from the lanai and upstairs balcony were awesome. Townhome was beautifully maintained and fully stocked. Thanks to Kelley and her daughter for a never-to-be-forgotten vacation.

Responds fast! avg. 2 hours 13 minutes

Match: Private fishing lake or river

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Price per night from

$138

Luxury Condo 2Bd/2Ba, 1st Flr, 1 mile to IMG Academy

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great place!” Like usual Shorewalk does not disappoint. However the condo we stayed at this time was above and beyond any others we have stayed at this far! Thank you James!

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$97

Gorgeous Home - Palma Sola Bay access Anna Maria

Bradenton house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$343

12 steps to the Beach; Florida Sun Coast Condo

St. Petersburg apartment

1 bedroom / 1 bathroom / sleeps 3

“Wonderful place” We arrived here and we're immediately enchanted with the location and view. The apartment is perfect for a couple and everything was in place, clean and with everything you need to start of a great vacation.

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Price per night from

$115

Private Beach Community-Close to Everything

St. Petersburg condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$95

Beautiful Waterfront Condo In Bradenton Florida, close to everything!

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Thank you Al and Patti” Thank you Al and Patti. Maria and I will always remember the comfort, warmth and beauty of your condo. The lovely decor and appointments lent themselves to a cheerful and soothing vacation experience. And we were so impressed by the quiet waterfront and its sights, along with the fine restaurants and shops all within walking distance. Thank you again for sharing your lovely condo..

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Price per night from

$101

Waterside at Coquina Key

St. Petersburg condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 1 minutes

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Price per night from

$149

HAVE IT ALL, WITHOUT BREAKING THE BANK, Just available Dec.in a lovely condo

Madeira Beach apartment

2 bedrooms / 1 bathroom / sleeps 6

“A relaxing and memorable vacation” A beautifully decorated condo 3-4 blocks from a great stretch of gulf coast beach. I'd recommend driving over if you want to bring chairs, cooler, etc. Beach parking is inexpensive. The condo itself is quiet, clean and lovely and offers a well-stocked kitchen, two good-sized bedrooms with comfortable queen beds, all linens (including beach towels), and cable TV in bedrooms and living room. Both saltwater and chlorinated pools on the premises. You can fish the Intercoastal Waterway from the yacht club piers. Great restaurants and John's Pass nearby. So much nicer than a hotel. The owner was great to work with. We hope to visit again.

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Price per night from

$116

Shorewalk Condo UD near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Winter vacation” Been to Bradenton many times to visit family. First vacation at Shorewalk. Great amenities and location. Will book again for another stay in the future.

Responds fast! avg. 1 hour 23 minutes

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Price per night from

$109

Lovely one story home on the water

Palmetto house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$287

Panoramic ocean views 1

St. Petersburg apartment

1 bedroom / 1 bathroom / sleeps 2

“Views are like a postcard!” 180 degrees of water views, which can be seen from the living room, dining room and kitchen. The balcony is amazing for enjoying a glass of wine, watching the sunset, watching dolphins swim by ( almost every day). Great utilization of space- there is a dining set for 2, and a cozy outdoor couch as well. The entire condo is unlike anything else we have stayed in before- everything is upscale finishes, even simple things... like the silverware, or plates in the kitchen! When we first walked in, the place felt like out of the cover of a home-design magazine. Thankfully, it was not only gorgeous, but functional too ( sometimes looks and comfort don't go hand-in-hand). Bed is some kind of amazing memory foam, and I noticed all down comforters and pillows were covered with hypoallergenic covers. So very comfortable, it was hard to get out of bed! Waterside feels like some type of a resort, palm trees and greenery everywhere. The pool can't be any closer to the bay... maybe 10 feet away! Super clean, heated pool surrounded by more palm trees. The jacuzzi tub was open late ( until 10pm), so it makes for a nice relaxing soak after a day at the beach, or exploring. Thank you, this was an amazing vacation and so hard to leave!

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Price per night from

$166

Shorewalk Condo BM near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Love staying at Shorewalk” If stated that it was on 2nd floor i missed it. pic was a ground level setting. i managed the steps.

Responds fast! avg. 1 hour 23 minutes

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Price per night from

$114

Beachfront Studio #1 Longboat Key

Longboat Key studio

Studio / 1 bathroom / sleeps 4

“Location! Location! Location!” The listing description and photos were accurate, this rental property is amazing. Studio #1 was tastefully decorated and very clean. We had beautiful views of the ocean from the living area. It was very spacious with plenty of room for three of us to spread out comfortably. It had lots of storage for our belongings, roomy bathroom with an extra open closet area and a wonderful kitchen area. 5 steps and your toes are in the sand and 40 more steps and you're in the water. A beautiful beach to walk, crystal clear water for swimming, the wildlife was awesome and sunsets were spectacular. James unfortunately had to come twice to let us in because we locked ourselves out, but he did so each time with a smile and friendly conversation. Right out front is an amazing wide sidewalk for bike rides to Bradenton Beach , St. Armand's Circle and to wonderful restaurants. Definitely found a great spot to settle in for a few weeks of relaxing fun in the sun. Thank you so much James and Cindy!!

Responds fast! avg. 2 hours 22 minutes

Match: Private fishing lake or river

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Price per night from

$243

Princess Hana Villa on the Manatee River- 2 Bedroom 2 Bathroom

Ellenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$138

Sunrise & Sunset- Bayfront and Private Gulf Beach!

Treasure Island apartment

1 bedroom / 1 bathroom / sleeps 4

“Sunset Cove” We had a great stay. The location across from the beach was excellent. Although the pool was quite cool due to solar heat the area was nice. Mickey the grounds keeper was the best, nice, laid back and helpful.

Responds fast! avg. 35 minutes

Match: Private fishing lake or river

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Price per night from

$91

#404 Waterfront condo with Stunning views! See the dolphiones from the balcony!

Madeira Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Wonderful apartment” Me and my family spent a week in apartment #310 and had a magnificent time. The apartment is fully equipt with everything you possibly could want for your vacation. Nice locaion. Beautiful view from the balcony. The information from the owners is very good. We really want to return some day!!!

Match: Private fishing lake or river

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Price per night from

$81

Cut House- Waterfront, dock, ocean access, beach

Palmetto house

3 bedrooms / 2 bathrooms / sleeps 6

“delightful” Three 60+ hockey players and their wives in search of a house close to the Ellenton Ice arena arrived here in april not knowing what to anticipate. We were delighted to find the accommodations exceptionally charming and clean. The views of the Manatee River were great and the traffic on "the Cut" was continually entertaining. The waterside amenities were superb and next time we'll rent a boat to keep at the dock. The "Naked Beach" next to the patio just off the dock might not have any surf but my tan is Just as even as can be and the proximity to the beer cooler was awesome. We recommend The Riverhouse and Blu Mangrove Grill for dining just ten minutes away. All in all the location, amenities, service, accommodations were top notch. Thanks "Cut House"!

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Price per night from

$287

Panoramic Ocean Views 2

St. Petersburg apartment

1 bedroom / 1 bathroom / sleeps 4

“Great place to stay” I stayed in this condo last February. It is calm, bright and perfectly clean. The balcony and the view on the water are outstanding! In addition to that, Sabina is perfectly organized, answered all the question I had and made sure I was feeling perfect. I definitely recommand it!

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Price per night from

$149

Shorewalk Condo CK near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Relaxing Week at Shorewalk Condos!” We had a very calm and enjoyable week renting a 2-bedroom condo. We enjoyed all the amenities that it had to offer especially the hot tub given the unseasonably chillier weather we had during our stay. The closeness to shopping, seafood and other restaurants, the movies, & various beaches/keys is fantastic. Pic was taken early morning of the lagoon in the back.

Responds fast! avg. 1 hour 23 minutes

Match: Private fishing lake or river

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Price per night from

$114

Charming Beach House in Longboat Key/ pool/pet/dock

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$263

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