Vacation Rentals & Beach Rentals in Siesta Key

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Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared indoor pool Linen provided

All filters match

Price per night from

$115

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Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$258

All Inclusive Executive Rental

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 57 minutes

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$166

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$422

4 Bed 3bath Water front home

Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$436

New York Avenue Rancher

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$444

Sarasota Vacation • 15 Minutes to Beach • Sleeps 6

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$194

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$489

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$489

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$489

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$138

Coastal Tiki 4/2 with outdoor paradise

Sarasota house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$456

Sarasota Rambler | Downtown MidMod Stay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$315

The cozy hideaway!

North Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$182

5 min drive to the beach 8 min to Siesta Key

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 1 minutes

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$206

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$548

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$423

Live Like a Local in the Heart of Sarasota!

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$251

Responds fast! avg. 4 minutes

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$126

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$290

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$295

A Comfortable getaway!

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$115

Just a mile to downtown Sarasota!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$98

Stay near the heart of Sarasota

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$115

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$659

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$266

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$266

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: Shared indoor pool, Linen provided

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$311

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Romantic place. Perfect for young families with small kids” Firshermans Cove is on a shore side. The views are amazing as well as beach which is clean and not crowded at all. Easy check in/out and very quiet place, was ideal in our case, young family with 1,5 old boy. It was nice stay and we hopefully come back again.

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$266

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$148

Cute Efficiency Apartment - nice neighborhood

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Great place to stay in sarasota” Very nice one bedroom apartment with everything you need. Close to everything. Quiet neighborhood. Just a great piece of mind renting from Terry had no worries at all.

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$103

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$303

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$311

Beachfront Getaway in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$224

Lido Sunshine L

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$171

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$95

Viewing 38 of 505
rentals in Siesta Key

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