Cottages Anna Maria Island

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58 cottages

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Children's pool

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Price per night from

$224

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1 of 2 match: Rental types, Children's pool

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Price per night from

$573

CFP! St.PeteBeach Rental for 4! 01/09-11/2017. College Football Nat'l Champs

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Children's pool

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Price per night from

$573

Remodeled Sunset Vistas 303N - Booking for Summer 2021, with No Cleaning Fees!

Treasure Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Children's pool

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Price per night from

$258

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Children's pool

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Price per night from

$149

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Children's pool

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Price per night from

$212

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Children's pool

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Price per night from

$859

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Children's pool

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Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Children's pool

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Price per night from

$172

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

1 of 2 match: Rental types, Children's pool

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Price per night from

$476

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Rental types, Children's pool

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Price per night from

$205

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Children's pool

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Price per night from

$192

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Rental types, Children's pool

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Price per night from

$114

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Children's pool

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Price per night from

$172

Sea Waves in Anna Maria Island with Private Dock

Anna Maria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Rental types

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Price per night from

$377

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$354

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$343

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$287

The Cannon- A two bedroom adorable cottage minutes walking to beach

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Rental types

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Price per night from

$401

The Anchor- A two bedroom cottage minutes walking to beach.

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Rental types

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Price per night from

$373

Luxury Beach Cotttage

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

1 of 2 match: Children's pool, Rental types

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Price per night from

$532

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

1 of 2 match: Children's pool, Rental types

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Price per night from

$245

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$458

“Charming studio in lovely quiet neighborhood with fenced in private outside area.” This studio has everything you'll need. It's located in a beautiful neighborhood, great for walking. There's a small park just down the road a couple of blocks where you can sit and watch the amazing sun sets or just enjoy watching the boats ride by. The owners are very nice and have a few fur babies of their own, so they may allow you to bring your doggie,too! Sue/Dawn......thank you!!!! I hope to return & stay again.

1 of 2 match: Children's pool, Rental types

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Price per night from

$229

Steps to Beach+bikes VaCay getaway on PaG island

St. Pete Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$182

HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!

Bradenton Beach cottage

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 15

1 of 2 match: Children's pool, Rental types

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Price per night from

$295

Songbird Cottage

Anna Maria Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$110

Starfish Cottages One Bedroom

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$139

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Rental types

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Price per night from

$745

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$163

Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks

Cortez cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$215

Sunset Beach Cottages - 2 Bedroom Beach Cottages

Treasure Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$343

Sunset Beach Cottages, 1 Bedroom Beach Cottages

Treasure Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$241

Villa Kailāsa. Pool, heated Spa, 6 min drive to the Beach!

Madeira Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$401

Guest House, 750 sq ft, private, with all amenities, parking and pool

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$98

A Private, Spacious and Modern Home Away From Home. Heated Pool. Bikes, Boards,

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$166

Steps to Sand - Standalone Beachfront Cottage w/ Picnic Area & BBQ Grill Nearby

Treasure Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Children's pool, Rental types

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Price per night from

$142

Fully equipped cottage directly on the beach. Comfort and an unbeatable locatio

Treasure Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Children's pool, Rental types

1 of 2 filters match

Price per night from

$189

Viewing 38 of 58
rentals in Anna Maria Island

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