Vacation Rentals & Beach Rentals in Siesta Key

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538 beach rentals

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private outdoor pool (heated) Swing set or jungle gym

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Price per night from

$230

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Englewood’s Paradise Home

Englewood house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$144

Rentalvilla-florida villa H

Rotonda West villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$173

Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$402

Paradise 4 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

North Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$431

Paradise 3 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

Braden River house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$373

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$574

Canal Front 3-Bedroom Grand Villa with Pool

El Jobean villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$190

Glorious Daze 4bedroom/4bath beachfront home with golf cart & elevator!

Holmes Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,378

Vaughan Place

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 6 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$173

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$517

Castaway Cottage

Holmes Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$391

FantaSea

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,492

Mango Island

Venice house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$517

Coastal Paradise! 5 mi to beaches! Heated Pool! Sleep up to 14

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,257

THE LIDO RESIDENCE

Lido Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$778

Coastal Oasis

Nokomis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$228

Turquoise Turtle

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$247

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$155

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$656

Captiva Paradise Home close to IMG Academy & Siesta Key Beach

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$373

Seasonal Rental

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$293

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$861

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$224

Venice Pool Home Centrally Located, Just Waiting For You

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$276

Beautiful home- Private getaway-Heated Pool/HotTub IMG 5 Close to Beaches

Palma Sola house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 22

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$832

Hibiscis Hideout Pool/Hot Tub Home

Pinecraft house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$259

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$212

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$298

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Trip to paradise” Renting unit was very easy. Unit was the best layout was great. Amenities within we're well thought, out and for us anything we wanted was there including beach chairs. View of ocean was breath taking along with sunsets. I will come back again.

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent location for a great vacation!” This is the fifth time we have had the pleasure of vacationing at El Galeon. We love the location with the beautiful beach access and walking to restaurants. We love the Manasota Key and have been vacationing there for the last seventeen years. El Galeon Gulf Unit 2 is our favorite place to stay with plenty of space and everything we need for a wonderful stay. We have already reserved "our place" for 2015.

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$303

Fishermans Cove FC Unit 205B *

Gulf Gate Estates condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Fishermans Cove FC Unit 310B 2

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great location!” The unit was just as described and pictures matched. The view of the ocean and bay were gorgeous. The kitchen was well equipped and there were lots of toys and chairs for the beach.

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$311

Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$266

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rentals in Siesta Key

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