Vacation Rentals & Beach Rentals in Anna Maria Island

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318 beach rentals

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Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: City breaks Pets allowed

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Price per night from

$234

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

Match: City breaks Pets allowed

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Price per night from

$194

Alice's Beach Bungalows Private Oasis TI, FL

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Short vacation” Still on our short vacation. So far everything is perfect! Susan has been very helpful with any questions and has been there anytime we had needed her. Hot tub is great! Place is super clean and efficient.

Match: City breaks Pets allowed

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Price per night from

$217

Historic Old Northeast Coastal Decorated 1 Bedroom

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: City breaks Pets allowed

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Price per night from

$144

Modern Studio, Designer Kitchen Walkable Downtown

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: City breaks Pets allowed

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Price per night from

$132

Sarasota Apartment in Downtown !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

Match: City breaks Pets allowed

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Price per night from

$189

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: City breaks Pets allowed

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Price per night from

$295

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

Match: City breaks Pets allowed

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Price per night from

$258

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: City breaks Pets allowed

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Price per night from

$482

Deluxe Queen Suite in Gorgeous Pop Art Gallery Pool Home Close to Everything!

St. Petersburg private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: City breaks Pets allowed

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Price per night from

$144

Tangerine Dream, Pet Friendly, Fenced Yard

Gulfport bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: City breaks Pets allowed

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Price per night from

$115

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: City breaks Pets allowed

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Price per night from

$229

Historic Pass-A-Grille, Literally Seconds to Beach

St. Pete Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: City breaks Pets allowed

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Price per night from

$298

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

St. Pete Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 9 minutes

Match: City breaks Pets allowed

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Price per night from

$337

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: City breaks Pets allowed

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Price per night from

$218

A Beautiful Bungalow in St Pete!

St. Petersburg house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: City breaks Pets allowed

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Price per night from

$345

Match: City breaks Pets allowed

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Price per night from

$183

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: City breaks Pets allowed

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Price per night from

$183

Perfect Getaway+ Patio- Close2 Beach+ Rays!

St. Petersburg house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 9 minutes

Match: City breaks Pets allowed

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Price per night from

$115

Close to all with a King-bed! Bikes included

St. Petersburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 9 minutes

Match: City breaks Pets allowed

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Price per night from

$79

Boho Vibe 3B/2B centrally located Alta Vista Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: City breaks Pets allowed

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Price per night from

$172

The Loft at Crescent Lake

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: City breaks Pets allowed

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Price per night from

$132

Cozy Steps2 Vinoy, Dali, Pier & Dtwn! patio+bikes

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 9 minutes

Match: City breaks Pets allowed

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Price per night from

$90

Delightful Oasis #2

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: City breaks Pets allowed

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Price per night from

$178

4Bed Spacious Home w/cocktail pool Minutes 2 dtwn St Pete!

St. Petersburg house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 9 minutes

Match: City breaks Pets allowed

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Price per night from

$324

Match: City breaks Pets allowed

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Price per night from

$138

Match: City breaks Pets allowed

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Price per night from

$295

The Moon Garden Apt at Crescent Lake

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: City breaks Pets allowed

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Price per night from

$161

Match: City breaks Pets allowed

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Price per night from

$138

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The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, City breaks

1 of 2 filters match

Price per night from

$345

Five star Downtown Sarasota tropical garden Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Paradise Found in Downtown Sarasota” Absolutely charming, fully redone/ upgraded bungalow close to everything Sarasota has to offer. This was the third year running my wife & I have stayed at the wonderful home located minutes from Sarasota's best beaches, restaurants & shopping. We fully intend to return again next year! The two bedroom home is in pristine condition. Beautifully decorated, lovely hardwood flooring throughout with a fully stocked (appliances, crockery, pots/pans, cutlery, etc...) kitchen & renovated bathroom. Everything you need is provided, just arrive & settle-in. A huge projection screen in the living room, should you want to have an at-home movie night (rental Dvd's a 5-minute walk away @ Publix). There's also a regular flat-screen TV in the living room, as well as a wall-mounted TV in the bedroom. The backyard is, personally, my favourite part of the home. A screen-in lanai to eat in & a beautifully manicured backyard to relax in under the tiki hut or under the palm trees. There are a few seating areas throughout the backyard. Find the space you like the best, sit-back & relax with a cool cocktail- very civilized & very beautiful. You'll feel like you're in the Caribbean, not Florida in this backyard. Maureen & Pat, your hosts who, very conveniently, live right next door have provided everything you need, including all the beach chairs, umbrellas, beach towels, etc...to take along with you to Sarasota's beautiful beaches. Maureen has also provided tons of literature about the area in the house- restaurant menus, local mags, maps- everything. Maureen & Pat are always happy to suggest restaurants, beaches, shopping, golf, etc. They know Sarasota well, are friendly & happy to help in any way they can to ensure you have a wonderful stay. My wife & I can honestly say we love this property, have encountered no negatives about the place in three years of week-long stays & look-forward to our time there each year. We recommend this lovely home to everyone.

1 of 2 match: Pets allowed, City breaks

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Price per night from

$189

RAVE REVIEWS; Directly across the st from beach ! Unit #2

St. Pete Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Pets allowed, City breaks

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Price per night from

$201

#1 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Pets allowed, City breaks

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Price per night from

$345

#2 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pets allowed, City breaks

1 of 2 filters match

Price per night from

$345

#5 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, City breaks

1 of 2 filters match

Price per night from

$345

#8 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Pets allowed, City breaks

1 of 2 filters match

Price per night from

$345

#10 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

1 of 2 match: Pets allowed, City breaks

1 of 2 filters match

Price per night from

$459

#9 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, City breaks

1 of 2 filters match

Price per night from

$345

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rentals in Anna Maria Island

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