We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Siesta Key Cottages

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
Payment
Select
Go to map view
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
loading...
Sort by
From
$127
/ Night
View Details
1 / 13
2 Bedrooms / 1 Bathroom / Sleeps 6
Overview Make Enquiry
From
$1,161
/ Night
View Details
1 / 23
7 Bedrooms / 5 Bathrooms / Sleeps 16
Overview Make Enquiry
From
$232
/ Night
View Details
1 / 9
4 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Enquiry
From
$459
/ Night
View Details
1 / 10
4 Bedrooms / 4 Bathrooms / Sleeps 10
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is one of the nicest rental properties that you will find on Siesta Key! It has views that are to die for of the bay looking east, south and north to Downtown skyline plus it has some Gulf of Mexico views looking west. All rooms in the house have something special to admire and enjoy. There... View all property information
Make Enquiry
From
$299
/ Night
View Details
1 / 12
4 Bedrooms / 3 Bathrooms / Sleeps 10
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Welcome to “Casa De Suenos”, one of the most fabulous vacation homes in Siesta Key. Newly constructed in 2013! The magic begins as you enter the foyer of this beautiful casa and gaze across the expansive living area, and deck area. You know already you made the right choice for your family and... View all property information
Make Enquiry
From
$160
/ Night
View Details
1 / 10
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is in a complex located on the GULFSIDE (or Beach side) of the island. It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and a bath and a half.... View all property information
Make Enquiry
From
$138
/ Night
View Details
1 / 4
1 Bedroom / 1 Bathroom / Sleeps 2
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Pygmy Palm is a comfortable Florida keys cottage on Siesta Key between Siesta Village and the #1 beach in the world. Shopping and dining are a few steps from your front door. The beach is a few steps in the other direction. Coffee first or beach first? These are your problems at Siesta Pearl.... View all property information
Make Enquiry
From
$124
/ Night
View Details
1 / 11
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Location, Location, Location! Siesta Key #1 Beach in USA Our condo is only a 3 minute walk to Crescent Beach on beautiful Siesta Key FL. Siesta Key Beach rated #1 beach in the USA. We rent by the month or for the season. Our two bedroom, two bath has a screened in lanai, large great room with all... View all property information
Make Enquiry
From
$494
/ Night
Payment Protection
View Details
1 / 17
3 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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 the crystal white sands of Siesta Keys number one beach are under your feet. We are located at the... View all property information
Make Enquiry
From
$266
/ Night
View Details
1 / 17
4 Bedrooms / 4 Bathrooms / Sleeps 12
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Villa Brisa Marina or 'Sea Breeze' at 1119-1121 Crescent Street is an exciting new 4BR/4BA/2Kit home just added to our boutique collection of fine vacation homes and it's sure to be a standout. This home features a brand new heated pool and a three minute walk to the Nation’s finest beach [no major... View all property information
Make Enquiry
Get the List
From
$232
/ Night
View Details
1 / 23
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Sea Wave Casita - 1119 *****During the fall season, enjoy the freedom of booking your travels with no worries over weather! We offer FREE travel insurance in September - mid November. Inquire with our reservationists! The Sea Wave and Sea Shell are two separate units which can be uniquely... View all property information
Make Enquiry
From
$232
/ Night
View Details
1 / 29
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Casita Sonrisa - 1117 *****During the fall season, enjoy the freedom of booking your travels with no worries over weather! We offer FREE travel insurance in September - mid November. Inquire with our reservationists! Welcome to Casita Sonrisa of Villa Fiesta! Enjoy an master bedroom featuring a... View all property information
Make Enquiry
From
$465
/ Night
View Details
1 / 26
4 Bedrooms / 4 Bathrooms / Sleeps 12
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Villa Cascada *****During the fall season, enjoy the freedom of booking your travels with no worries over weather! We offer FREE travel insurance in September- mid November. Inquire with our reservationists! Point of Rocks, located just south of the Stickney Point Bridge, the most notable location... View all property information
Make Enquiry
From
$407
/ Night
View Details
1 / 27
4 Bedrooms / 2 Bathrooms / Sleeps 12
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
La Casa Verde *****During the fall season, enjoy the freedom of booking your travels with no worries over weather! We offer FREE travel insurance in September- mid November. Inquire with our reservationists! The waterfront cottage, 'La Casa Verde' is a very luxurious and large four [4] bedroom... View all property information
Make Enquiry
Enquire for rates
1 / 25
4 of 5 stars (1) Very good
3 Bedrooms / 2 Bathrooms / Sleeps 10
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
3 bed on Beach Rd. with some Gulf view. This remodeled townhouse is a one of a kind property. Three bedroom with king, queen, 2double beds and living room sleeper sofa. This is a step out to the sand property just north of Siesta Key Beach. Walk to Siesta Village. Views of the Gulf from almost... View all property information
Make Enquiry
From
$256
/ Night
View Details
1 / 32
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
You could throw a tennis ball into the gulf from these Siesta Key beachfront condos at Fisherman's Cove! Located at Turtle Beach on the island of Siesta Key off Sarasota, Florida, these vacation homes have the best of both worlds - the beach in front and the intercoastal and boat docks in back.... View all property information
Make Enquiry
From
$465
/ Night
View Details
1 / 26
5 Bedrooms / 3 Bathrooms / Sleeps 14
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Pura Vida Oasis *****During the fall season, enjoy the freedom of booking your travels with no worries over weather! We offer FREE travel insurance in September- mid November. Inquire with our reservationists! This spectacular bright cheerful, canal front cottage with heated pool & spa has 5... View all property information
Make Enquiry
From
$465
/ Night
View Details
1 / 43
4 Bedrooms / 4 Bathrooms / Sleeps 12
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Villa Brisa Marina *****During the fall season, enjoy the freedom of booking your travels with no worries over weather! We offer FREE travel insurance in September- mid November. Inquire with our reservationists! Villa Brisa Marina or 'Sea Breeze' at 1119-1121 Crescent Street is an exciting new... View all property information
Make Enquiry
From
$174
/ Night
View Details
1 / 24
2 Bedrooms / 1 Bathroom / Sleeps 6
Overview Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located near the South Village of Siesta Key. This newly updated 2 bedroom duplex has it all. A new dipping pool to cool off the hot summer days, along with a BBQ and fire pit for the winter. Lots of space, all new furnishings throughout the home, the large eat in kitchen has plenty of room for... View all property information
Make Enquiry
From
$290
/ Night
View Details
1 / 12
3 Bedrooms / 3 Bathrooms / Sleeps 6
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Private Outdoor...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Island Bliss is one of the most elegant and comfortable houses that Siesta Key has to offer. This is one of the rare houses that is conveniently located behind The Village of Siesta Key and still has its own private dock on a canal. Ride your bike or walk to the beach and all the great shops and... View all property information
Make Enquiry
From
$215
/ Night
View Details
1 / 1
Studio / 1 Bathroom / Sleeps 2
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Newly remodeled -Queen Murphy Bed -Convenience Kitchen -Laundry Facilities on site -Patio / Grill -VCR/DVD -WiFi -Microwave NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do NOT always keep this calendar current. Thanks. Visit our site to see more photos and descriptions:... View all property information
Make Enquiry
Enquire for rates
1 / 16
4 of 5 stars (3) Very good
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
PLEASE NOTE: The Price displayed here is NOT ACCURATE! (It does not take the "Seasonal Rate" into consideration) - Sorry - this is Flipkey's stupid policy, not mine! This luxury third floor condo is bright and airy with its extra long Lanai! The Lanai (screened porch) overlooks the Gulf, Crescent... View all property information
Make Enquiry