Siesta Key Vacation Rentals

Welcome to Siesta Key. Scroll down this page to find your favorite travel destination in Siesta Key and browse our extensve inventory of accommodations in Siesta Key. Leisure travelers planning their family vacations can get offers directly from owners of Siesta Key vacation homes or houses in Siesta Key. Sometimes these single rental units are referred to as Siesta Key cabins or Siesta Key villas. Other popular lodging options include vacation rentals in Siesta Key, Siesta Key apartments and condos in Siesta Key. For business travelers we offer several convenient hotels in Siesta Key or small boutique hotels in Siesta Key area, many with the ability to book online. If you are planning a romantic getaway in Siesta Key, we highy recommend our unique inventory of bed and breakfasts in Siesta Key. B&Bs can also referred as small country inns in Siesta Key.

Finding the perfect vacation rental property can be very time consuming. Unlike many other sites out there that demand travelers (like you) to invest countless hours browsing though each vacation rental listing, at we make it easy for travelers to find best Siesta Key vacation rentals using our free inquiry service or Siesta Key lodging locator service. Save time searching for Siesta Key rental vacations and Siesta Key accommodations! Simply click the "Inquire Now" button, complete a short inquiry form, and within minutes you will start receiving multiple offers from Siesta Key vacation home rentals owners as well as from Siesta Key resorts, Siesta Key cabin rentals, and Siesta Key vacation homes.

Let Rentalo help you find the perfect place to stay for your next family vacation in Florida area. Our engine will match your specific inquiry criteria with each Siesta Key vacation rental listing, Siesta Key vacation house or Siesta Key villa in our Siesta Key rental vacations inventory. Finding Siesta Key vacation rentals by owner is easy with our free inquiry service. However, you can also browse our inventory of Siesta Key accommodation listings (as listed below) or use the SmartSearch tool to narrow down your search for Siesta Key lodging in Florida.

Enter your travel dates and number of people traveling (sleeps) and use one of the following search options:

  1. Inquire on ALL Vacation Rentals in Siesta Key. Click "Inquire Now" (Fastest Option - Receive the most Offers)
  2. Inquire on Selected Vacation Rentals in Siesta Key. Click "Check to inquire", then click "Inquire Now" (Time-Saving Option - Receive Offers from Selected Properties)
  3. Inquire only on a Specific Siesta Key Vacation Rental (Take the time to review each property - Receive an offer on the Property you like)
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.

ID: 386848
Palm Bay Club G46 Siesta Key FL, Heated Pool, Gulf - Vacation Rental in Siesta Key
1 Bedrooms
Sleeps 4
The accolades keep pouring in. Guests and media alike rate the palm bay club as a perfect destination for romantic getaways and family vacations. treat yourself to an idyllic holiday on florida's gulf ...Read Full Description
ID: 386848
Siesta Key Our House at the Beach 222, with Heated - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 4
There's plenty of room for everyone here at our house. We have a split-level living/dining area, with a large living room made for a crowd! the huge sectional sofa faces our new hdtv with dvd player, ...Read Full Description
ID: 386848
Crystal Sand 406, 4th floor, Gulf View, 2 heated P - Vacation Rental in Siesta Key
1 Bedrooms
Sleeps 4
Every sunset is a memorable experience at our condo at crystal sands 406 in siesta key. Overlooking the placid gulf of mexico, our 4th-floor condo on the shores of crescent beach is a great venue for ...Read Full Description
Check to Inquire *
ID: 388816
Sun n Sea - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 4
2 bedroom 1 bath condo on siesta key beach side duplex located in south village enjoy the relaxed siesta key lifestyle at this comfortable 2 bedroom duplex on the beach side, just steps to award winni ...Read Full Description
ID: 385207
Siesta Key Townhouse - Vacation Rental in Siesta Key
Sleeps 4
Lovely two bedroom, two and a half bath townhouse on the intercoastal waters of siesta key. Has three lanai's, one enclosed off the living... ...Read Full Description
Check to Inquire *
ID: 385217
Private villa - Vacation Rental in Siesta Key
Sleeps 4
A private 2 bedroom, 1 1/ bath villa located on the gulfside of siesta key. The villa is just a short walk from the beautiful, white beach and complex pool.... ...Read Full Description
ID: 385216
Sun, Sand & Save 20% to 35% at Midnight Cove - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 4
Sun, sand & *save 20% to 35% per week* at midnight cove in siesta key, fl direct-with-owner all-in price discounted rental rates from $658 to $1,389 /wk (variable season rates) & savings from ...Read Full Description
ID: 26753
Midnight Cove II Bayside 2 BR Condo #734 - Vacation Rental in Siesta Key
From USD999 wk
2 Bedrooms
Sleeps 5
Siesta key condo with boat dock available. Very clean 2 bedroom, 1 1/2 bath fully furnished top floor siesta key vacation rental condo with private entrance in beautiful complex. privately owned/manag ...Read Full Description
ID: 61870
Banyan Tree Beach Resort - Siesta Key, Florida - Vacation Rental in Siesta Key
From USD220 nt
2 Bedrooms
Sleeps 6
Siesta key vacation rental accommodations with the cozy feeling of home. Owner/managers have provided all the creature comforts to make your stay on siesta key truly a memorable vacation. upon arrivin ...Read Full Description
ID: 26680
 Casa Blanca Beach Rental  Siesta Key 1 & 2BR Apar - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 6
Your ideal choice for sarasota beach front condominium accommodations, the casa blanca on siesta key provides lodging directly on siesta key beach. Choose between magnificent gulf of mexico beach view ...Read Full Description
ID: 391955
CA704N- Fantastic Gulf Front View Condo - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 6
Ca704n beautifully appointed, fantastic gulf front view condo. Entire condo was refurbished in 2003 and repainted in 2012. light, bright kitchen with corian counters makes meal prep a breeze. if this ...Read Full Description
ID: 26753
Siesta Key Private Pool Home - Vacation Rental in Siesta Key
From USD6400 mo
3 Bedrooms
Sleeps 6
Siesta key beach house with electric heated pool. This pool is on sunny side of home. across street from siesta key public beach a 2 minute walk. private, immaculate, beautiful 2100 square foot single ...Read Full Description
ID: 385140
Ground Level Condo  - Vacation Rental in Siesta Key
From USD625 wk
2 Bedrooms
Sleeps 6
Ground level, 2br/2ba condo, located across from siesta key beach. This very nice unit is completely furnished for you to have a great vacation, including beach chairs and a small cooler. fully equipp ...Read Full Description
ID: 21353
From USD135 nt
2 Bedrooms
Sleeps 6
Aaa 2-diamond rated & trip advisor recommended located at crescent royale condominiums - one of the finest gated communities on siesta key - this 2 bedroom/2 bath privately owned vacation condo is ...Read Full Description
Check to Inquire *
ID: 383104
Sandy Toes - Vacation Rental in Siesta Key
From USD1800 wk
2 Bedrooms
Sleeps 6
Siesta key vacation home - townhouse - beachside - heated pool - voted #1 beach ! walk to shopping, restaurants, and boat rentals. 2 bedroom 2 bath with vaulted ceiling and a fireplace - garage - wash ...Read Full Description
Inquire on multiple properties - Save time! Inquire, Compare offers, and Book.

Smart Search

Sleeps: 1 Remove 1

remove all
*Traveling Dates:

Flexible Dates
(vacation rentals only)
Studio (1)
1 (8)
2 (31)
3 (2)
4+ (1)

Vacation Rental Types:
Apartment (35)
Cottage (1)
Home (2)
Townhouse (1)
Villa (2)

Lodging Types:
Hotels (1)
Vacation Rentals (44)

Location Attributes:
Beachfront (21)
Near water (9)
Waterfront (5)

Air Conditioning (41)
Full Kitchen (39)
Cable/Satellite TV (28)
Microwave (41)
Utensils (40)
Coffee Maker (39)

Things To Do:
Shopping (41)
Restaurants (27)
Swimming (39)
Boating (38)
Golf (34)
Jet Skiing (37)

Special Features:
Children Welcome (46)
Smoking Permitted (9)
Pet friendly (25)
Handicap accesibility (36)

Add these vicinities to my search:
Note: Use Search Destination box (above) to browse listings in these vicinities.
Longboat Key (12)
Sarasota (33)
Osprey (2)
Nokomis (2)
Bradenton (18)
Venice Fl (47)
Bradenton Beach (2)
Anna Maria Island (16)

Max Budget per Night: