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:

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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
ID: 5536
Ground Floor Condo at MidnightCove 11 - Vacation Rental in Siesta Key
From USD825 wk
2 Bedrooms
Sleeps 4
Come and spend time in ground floor siesta key vacation condo at midnightcove 11, the perfect vacation spot! the waterfront condo can sleep up to four guests comfortably and it features 2 bedrooms and ...Read Full Description
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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
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ID: 25942
Turtle Beach - Vacation Rental in Siesta Key
From USD1150 wk
2 Bedrooms
Sleeps 6
This recently remodeled condominium is clean and beautiful! the lanai (screened porch) is directly on the gulf, perfect for those romantic dinners and sunsets! this unit has two separate and private b ...Read Full Description
ID: 392315
Siesta Key Florida Island Condo with Pool - Vacation Rental in Siesta Key
From USD1000 wk
2 Bedrooms
Sleeps 4
Our new unit are truly a site to see. 2 br / 2 bath completely remodeled, newly furnished unit with fully equipped kitchen, cable tv, wifi, and washer/dryer. enjoy a resort style pool area beautifully ...Read Full Description
ID: 26552
Endless Summer, Ocean View - Siesta Key, Florida - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 6
For rent by owner, this luxurious 1540 sq ft two-bedroom/two bath siesta key vacation condo near to sarasota and the beach. This siesta key condo rental is newly remodeled, furnished and it has a priv ...Read Full Description
ID: 26701
Sunset Beach Resort Siesta Key - Vacation Rental in Siesta Key
3 Bedrooms
Sleeps 8
Two story, 3 bedroom, 2 bath unit, designer decorated, with amazing views of the gulf from every room! look no further. This unit has everything imaginable and you literally step out of your unit and ...Read Full Description
ID: 390070
Siesta Key Beach House - Vacation Rental in Siesta Key
Situated directly on the sand, our home is located less than half a mile south of the public beach on siesta key. The village on siesta is just a five minute electric car ride with jerry's free rides, ...Read Full Description
ID: 311641
Tropical Sun Condo - Vacation Rental in Siesta Key
Sleeps 2
Thank you for your interest in our resort! unfortunatley, none of our rooms are beach front. We are on the beach side of the road, but there are no beach views....welcome to the friendliest unit on si ...Read Full Description
ID: 111609
Casa Blanca - Gulf Side Private 2 BDR 2 BATH Villa - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 6
This 2 bedroom 2 bath free standing villa is located on the gulf side of midnight pass road, just steps away from the beautiful crescent beach. There is a king size bed in the master bedroom and two t ...Read Full Description
ID: 131717
Bay Oaks Condo,Florida > Siesta Key - Vacation Rental in Siesta Key
Sleeps 4
Bay oaks, a siesta key resort, is set amidst lush, tropical foliage on the intercoastal waterway, across from the gulf of mexico and world famous crescent beach with soft, sugar-white sand. Enjoy shel ...Read Full Description
ID: 143299
Paradise Cove Condo - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 4
Siesta key condo vacation rental - fore rent by owner - for sale by owner fully furnished, remodeled and updated in modern style, paradise cove is one of the best siesta key vacation condo rentals in ...Read Full Description
ID: 33925
Bungalows by the Sea - Vacation Rental in Siesta Key
From USD95 nt
2 Bedrooms
Sleeps 4
We are a cozy and comfortable. Privately owned 2 unit beach vacation rental house in siesta key. our vacation rental home is just a few steps to the powder white sands of crescent beach. our accommoda ...Read Full Description
ID: 386848
Siesta Key Gulf and Bay 204G Beach Front, 3 pools, - Vacation Rental in Siesta Key
2 Bedrooms
Sleeps 6
Nicest and most beautiful property on the siesta key beach. So writes a happy guest - and who are we to disagree? and, now the condo was just upgraded in 2010 with stainless steel kitchen appliances, ...Read Full Description
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Smart Search

*Traveling Dates:

Flexible Dates
1+ (46)
3+ (44)
6+ (23)
11+ (1)

(vacation rentals only)
Studio (1)
1 (9)
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 (45)

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 (49)
Smoking Permitted (12)
Pet friendly (28)
Handicap accesibility (38)

Add these vicinities to my search:
Note: Use Search Destination box (above) to browse listings in these vicinities.
Longboat Key (14)
Sarasota (46)
Osprey (4)
Nokomis (3)
Bradenton (21)
Venice Fl (48)
Bradenton Beach (6)
Ellenton (4)
Anna Maria Island (16)

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