Vacation Rentals in Siesta Key Florida

BOOK FROM THE SOURCE

Book Direct with a Vacation Rental Management Company & Enjoy the Best Rates and Services.

SIESTA KEY


Number of Guests

Bedrooms

Bathrooms
more filters

Price Range

Amenities
  Air Conditioning
  Dishwasher
  Fireplace
  Grill
  Hot Tub (Private)
  Luxury
  Pets Allowed
  Pool (Private)
  Ski-in/Ski-out
  Washer/Dryer
  Wheelchair Accessible

Activities and Interests
  Beach
  Biking
  Boating
  Canoeing
  Casino
  Corporate and Executive
  Disney
  Family Vacations
  Fishing
  Deep Sea Fishing
  Fly Fishing
  For Sale
  Golfing
  Group and Reunion
  Hang Gliding
  Hiking
  Honeymoon
  Horseback Riding
  Hunting
  Kayaking
  Lake
  LegoLand
  Mountain Biking
  Nightclub and Disco
  Over 55 Community
  Rental Exchange
  Sailing
  Scuba Diving
  Skiing
  State National Parks
  Cross Country Skiing
  Snowmobiling
  Spa
  Specials
  Surfing
  Theatre
  Ultra Luxury
  Wedding
  White Water Rafting
  Wind Surfing
  Wineries and Vineyards

SARASOTA AREA DESTINATIONS

Map of Siesta Key

TRENDING IN SIESTA KEY

The Crystal Classic

The Crystal Classic
by Anthony Vaarwerk

The Vacation Rentals listed below are represented by Professional Property Management Companies who know the Siesta Key area and have access to several properties.

These property managers provide local hospitality, additional services, and the very best in rates and availability while managing properties that are safe for you and your family. They will assist you in finding the right vacation rental for your vacation.

BOOK FROM THE SOURCE

Book Direct with a Vacation Rental Management Company & Enjoy the Best Rates and Services.


Huge Private Back Yard
$129/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Tropical Breeze Resort

The Hummingbird Siesta Key Florida
Resort in Siesta Key Florida
Studio • 1 Full Bath • Sleeps 2

Quaint Cottage. Sleeps 6. Private Heated Pool
$229/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Tropical Breeze Resort

Penthouse rental in Siesta Key Florida 4 bedrooms with pool and 1 block to beach and village
$350/night
Penthouse in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Amazing game room!
$189/night
Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Tropical Breeze Resort

Lanai View
$142/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Crystal Sands on Siesta Key

3 Bed. 3 Bath. Sleeps 9 in Beds. 1 Block to Village & Beach
$199/night
Bungalow in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties

Private Heated Pool and Spa with SunShelf and Swim Up Bar
$500/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Lido Key Vacations

Roof Top Deck - Amazing Sunset, Beach, and Gulf Views
$550/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Lido Key Vacations

Large home rental close Beach and Siesta Village with pool and 8 bedrooms sleeps 22 pet friendly
$500/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties

Plenty of space for 4 or more vehicles, Access to Left side
$500/night
Townhouse in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 17
Lido Key Vacations

Tower 0305 Siesta Key Florida  Crystal Sands on Siesta Key
$229/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Crystal Sands on Siesta Key

Exterior of the home from the Street
$249/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 12
Tropical Breeze Resort

Sea Shell 207 Siesta Key Florida Sea Shell Condos
$265/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Sea Shell Condos

What a Backyard!
$500/night
Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Tropical Breeze Resort

Pool Area and Balcony Area
$199/night
Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Tropical Breeze Resort

Living space
$129/night
Townhouse in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 9
Lido Key Vacations

Front of Home. Fence to Pool Area
$159/night
Condo in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Tropical Breeze Resort

Pull up your boat and dock right at the house
$500/night
Townhouse in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 17
Tropical Breeze Resort

What a Backyard!
$500/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Lido Key Vacations

8 Bedrooms - Sleeps 25 - Steps to Beach - Private Pool
$500/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Lido Key Vacations

Siesta Key Vacation home with 3 bedrooms close to the village and beach
$169/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Stunning 4 Bed with Large Loft. Huge Back Yard Pool Area
$450/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Lido Key Vacations

Florida Gulf Coast beachfront vacation rental with 2 bedrooms in Siesta Key
$214/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Crystal Sands on Siesta Key

Tower 0304 Siesta Key Florida  Crystal Sands on Siesta Key
$315/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Crystal Sands on Siesta Key

Beautiful Furnishings and Large Open Floorplan
$249/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Tropical Breeze Resort

4 Bedroom 2.5 Bathroom Townhome - Walk to Beach
$229/night
Siesta Key Florida
4 Beds • 2 Full Baths • Sleeps 12
Tropical Breeze Resort


IDEA DRIVEN VACATIONS

Where to stay around Siesta Key Florida

Our October 2020 property listings offer a selection of 181 vacation rentals near Siesta Key. Find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Siesta Key for a holiday or a weekend are on Find Rentals.


Where are the best places to stay in Siesta Key?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Siesta Key:

  • Florida Gulf Coast: 2,258 vacation rentals
  • Florida Emerald Coast & Destin Area: 1,512 vacation rentals
  • Florida Keys: 618 vacation rentals

For nearby neighborhoods, please use our search to access the selection of vacation rentals available in and around Siesta Key.


What are some fun things to do in Siesta Key?

Find Rentals offers a selection of vacation rentals near parks and other areas of interest in Siesta Key. Some of the most popular places to visit while you're traveling in Siesta Key while on vacation are South Lido County Park, Nora Patterson Bay Island Park, Boyd Park, Highland Park, Ted Sperling Nature Park at South Lido and a few more.

There are many other points of interest around Siesta Key listed on Find Rentals where you can find a great place to stay. Try out the search to find a large selection of vacation rentals available near the city or region you're traveling to.


Which vacation rental managers have properties for rent in Siesta Key Florida?

  • Tropical Sands Accommodations: 0 vacation rental properties
  • Tropical Beach Resorts: 14 vacation rental properties
  • Siesta 4 Rent: 0 vacation rental properties

Can I rent condos in Siesta Key?

Yes. Find Rentals has 103 condos available for rent in Siesta Key. Our other popular types of vacation rentals in Siesta Key include:

  • Houses : 49 rentals available
  • Villas : 34 rentals available
  • Cottages : 24 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including duplexes and more.


Can I rent fishing rentals in Siesta Key?

Absolutely, Find Rentals has 231 fishing rentals in Siesta Key. You have also many other possibilities in Siesta Key area, including:

Please use our search bar to access the selection of vacation rentals.


How can I find a vacation rental manager in Siesta Key?

Find Rentals is the premiere guide for Vacation Rental Managers. We work with management companies from all over the world to provide you with the most robust selection of professionally managed rentals. Use the search to access the selection of management companies and rentals available.





  • luxury vacation rentals sarasota area
  • siesta key vacation rentals
  • vacation rentals by owner in siesta key
  • pet friendly vacation rentals sarasota area
  • cheap vacation rentals in siesta key