Cottages Sarasota

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35 cottages

Manatee River Cottage in Historic Old Town

Palmetto cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Match: Rental types Cot available

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Price per night from

$148

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Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Rental types, Cot available

1 of 2 filters match

Price per night from

$2,846

Hibiscis Hideout Pool/Hot Tub Home

Pinecraft house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Cot available

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Price per night from

$258

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Cot available

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Price per night from

$178

-Spacious Clean 3 bed 2 bath with King Bed. Fresh remodel. Short 5 min to beach-

South Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Cot available

1 of 2 filters match

Price per night from

$292

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Cot available

1 of 2 filters match

Price per night from

$230

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, Cot available

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Price per night from

$478

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

1 of 2 match: Rental types, Cot available

1 of 2 filters match

Price per night from

$190

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Rental types, Cot available

1 of 2 filters match

Price per night from

$149

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Rental types

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Price per night from

$356

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: Cot available, Rental types

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Price per night from

$534

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: Cot available, Rental types

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Price per night from

$246

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: Cot available, Rental types

1 of 2 filters match

Price per night from

$460

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

Bradenton Beach cottage

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 15

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$296

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$158

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: Cot available, Rental types

1 of 2 filters match

Price per night from

$748

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$225

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$345

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: Cot available, Rental types

1 of 2 filters match

Price per night from

$160

Songbird Cottage

Anna Maria Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$110

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

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$373

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

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$401

Responds fast! avg. 16 minutes

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$127

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$338

The Guesthouse (near Lakewood Ranch)

Lakewood Ranch cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$161

Sea Waves in Anna Maria Island with Private Dock

Anna Maria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$377

South Venice Cottage

South Venice cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$132

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: Cot available, Rental types

1 of 2 filters match

Price per night from

$212

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$132

“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: Cot available, Rental types

1 of 2 filters match

Price per night from

$229

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$97

Cortez Gardens Cottage 15 , Renovated, Close to Beach, 3-Bed, 2 Bath 10 people

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$228

Moon Dreams Cottage - Pet Friendly

Nokomis cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$113

***Bermuda-esque Island Cottage! Steps to Sand!***

Longboat Key cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$176

AMI Tree House

Bradenton Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 7 minutes

1 of 2 match: Cot available, Rental types

1 of 2 filters match

Price per night from

$241

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