Cottages Siesta Key

/ Home
/ Vacation Rentals
/ United States
/ Florida
Book with confidence.

Updating...

age 0-16
133 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

133 cottages

Why am I receiving these results?

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.

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$532

These homes match some but not all of your filters. Clear all filters

Siesta Key Beach | Private Pool

Fruitville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$252

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 59 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,002

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. 1 hour 59 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,850

BeautifulHome with Pool - 3 miles from Siesta Key Beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$241

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$274

Updated 4/2 pool home, 5 Mins to Siesta Key

Siesta Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 26 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$327

New Coastal Pool + Game Room home - sleeps 10

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$567

Zen Bungalow

Sarasota house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$201

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$229

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$150

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$744

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$228

Lower Prices! Walk to Village, Heated Saltwater Pool

Siesta Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Beautiful and clean private home with pool and close to everything!” The home was in walking distance to village and beach. Beautiful and clean home with private pool. The home had everything that we could ask for. We had an outstanding time on our vacation. We will definitely return to this home again.

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$196

Priced Right Near Arlington Park Outdoor Kitchen

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$186

Lower Prices! Private Pool, WiFi, King Master w/En-suite, Garage, Washer/Dryer,

Gulf Gate Estates house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$121

Large Private Home, 5 Min Walk to Beach, Pool

Gulf Gate Estates house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$761

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$340

Steps to Siesta Key Beach, Pool/Spa/Tiki Bar

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$316

Private Pool, 6 Mins Beach, 2 Family Rooms, Cable

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$162

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$249

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$264

Private & Quiet Pool Home on Cul-de-sac, Garage, WiFi/Cable, BBQ, Dog Friendly,

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$174

Great Private Pool, Heat Extra, 2.5 miles to Beach, Dog Allowed, WiFi/Cable, BB

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$131

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$103

Home with Private Pool, Fenced Yard, Smart TV, Single Car Garage, BBQ

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$116

Midcentury modern pool home on Siesta Key w/ gorgeous backyard

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$303

Pool, 2 Mi. to Beach, WiFi, Walk to Cafes, Dog OK

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$121

Large Pool Home, BBQ, YouTube TV, One Level

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$136

Mid Century Modern Canal Home, Pool, King Master

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$305

Lower Pricing! Stunning Heated Pool, Lanai w/ TV

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$184

Added New Pool! South Sarasota Home, 10 Min to Siesta Key, Wi-Fi, Screened Patio

Gulf Gate Estates house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$148

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$329

New Listing Fully Renovated, Saltwater Pool, Smart TV’s /WiFi, Covered Parking,

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$203

Responds fast! avg. 4 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$273

Doveplum 721 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$167

Viewing 38 of 133
rentals in Siesta Key

×

Also consider