Siesta Key Holiday Rentals
81 Siesta Key Holiday Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Siesta Key, SW Gulf Coast, Florida, United States.
>> Florida
>> Siesta Key
SW Gulf Coast Top Cities
Condo:
1 Bedroom, 1 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: The Palm Bay Club offers all of the amenities of the finest resort hotels in a unique condo environment. Enjoy great comfort and value in this gul... Learn More
Location: Siesta Key, Florida, United States
Description: The Palm Bay Club offers all of the amenities of the finest resort hotels in a unique condo environment. Enjoy great comfort and value in this gul... Learn More
Rates
$125 - $400 night
$575 - $1795 week
$125 - $400 night
$575 - $1795 week
Special Offer Apr 17 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 1 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida - Crescent Beach. The 2 bedroom, 1 bath villa is 1000 sq. ft. It has a large living area, dining area... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida - Crescent Beach. The 2 bedroom, 1 bath villa is 1000 sq. ft. It has a large living area, dining area... Learn More
Rates
$146 - $218 night
$1022 - $1526 week
$146 - $218 night
$1022 - $1526 week
Condo:
1 Bedroom, 1 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: The Palm Bay Club offers all of the amenities of the finest resort hotels in a unique condo environment. Enjoy great comfort and value in this gul... Learn More
Location: Siesta Key, Florida, United States
Description: The Palm Bay Club offers all of the amenities of the finest resort hotels in a unique condo environment. Enjoy great comfort and value in this gul... Learn More
Rates
$125 - $400 night
$695 - $1995 week
$125 - $400 night
$695 - $1995 week
Condo:
1 Bedroom, 1 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: 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 ... Learn More
Location: Siesta Key, Florida, United States
Description: 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 ... Learn More
Rates
$518 - $1249 week
$518 - $1249 week
Special Offer May 18 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 1 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida, Crescent Beach - This lovely 2 bedroom, 1 bath villa is located on the widest part of Crescent bea... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida, Crescent Beach - This lovely 2 bedroom, 1 bath villa is located on the widest part of Crescent bea... Learn More
Rates
$146 - $218 night
$1022 - $1526 week
$146 - $218 night
$1022 - $1526 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in an oceanfront complex, it will pamper you with b... Learn More
Location: Siesta Key, Florida, United States
Description: Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in an oceanfront complex, it will pamper you with b... Learn More
Rates
$518 - $1249 week
$518 - $1249 week
Featured
Special Offer Feb 2 - Oct 1 20% Septermber rentals excluding Labor Day - enter ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida - Crescent Beach. This luxury apartment is part of Island House Beach Resort, which is located on 280... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida - Crescent Beach. This luxury apartment is part of Island House Beach Resort, which is located on 280... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Featured
Special Offer Feb 5 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 1 1/2 bath villa is approx. 1000 sq. ft. It has a large livi... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 1 1/2 bath villa is approx. 1000 sq. ft. It has a large livi... Learn More
Rates
$152 - $232 night
$1064 - $1624 week
$152 - $232 night
$1064 - $1624 week
Featured
Special Offer Mar 7 - Oct 1 20% Septermber rentals excluding Labor Day, enter ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the widest part of Crescent Beach. It is approx. 100... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the widest part of Crescent Beach. It is approx. 100... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer Feb 10 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - The large 2 bedrooms, 2 bath unit is appox. 1000 sq. ft. It has a large living room... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - The large 2 bedrooms, 2 bath unit is appox. 1000 sq. ft. It has a large living room... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer Mar 23 - Oct 1 20% September rentals excluding Labor Day - enter ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Crescent Beach, Siesta Key. Gulf Front Unit, 3rd Floor, Panoramic Views. This luxury apartment is 1300 sq. ft. and is 2... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Crescent Beach, Siesta Key. Gulf Front Unit, 3rd Floor, Panoramic Views. This luxury apartment is 1300 sq. ft. and is 2... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer Feb 5 - Oct 1 20% September rentals excluding Labor Day - enter ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida - Crescent Beach - This 2 bedroom, 2 bath villa is 1000 sq. ft and is just steps to the white sandy ... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida - Crescent Beach - This 2 bedroom, 2 bath villa is 1000 sq. ft and is just steps to the white sandy ... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer Mar 30 - Oct 1 20% September rentals excluding Labor Day - enter ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort!! Siesta Key Florida. This 2 bedrooms, 2 bath unit is 1300 sq. ft. and is located on one the finest beaches in Florida. I... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort!! Siesta Key Florida. This 2 bedrooms, 2 bath unit is 1300 sq. ft. and is located on one the finest beaches in Florida. I... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer Apr 7 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta key florida, Crescent Beach - This large villa is appox. 1000 sq. ft. It is 2 bedrooms, 11/2 bath. It has a larg... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta key florida, Crescent Beach - This large villa is appox. 1000 sq. ft. It is 2 bedrooms, 11/2 bath. It has a larg... Learn More
Rates
$152 - $232 night
$1064 - $1624 week
$152 - $232 night
$1064 - $1624 week
Special Offer Feb 21 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath unit is approx. 1000 sq. ft. It has a large living ar... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath unit is approx. 1000 sq. ft. It has a large living ar... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer May 18 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - The large 2 bedroom, 2 bath villa is appox. 1000 sq. ft. It has a large living area... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - The large 2 bedroom, 2 bath villa is appox. 1000 sq. ft. It has a large living area... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Decked in tropical style, Siesta Dunes 104 is an ideal choice for families to spend their daytime hours at the pool or the gorgeous on-site beach. ... Learn More
Location: Siesta Key, Florida, United States
Description: Decked in tropical style, Siesta Dunes 104 is an ideal choice for families to spend their daytime hours at the pool or the gorgeous on-site beach. ... Learn More
Rates
$119 - $350 night
$575 - $1595 week
$119 - $350 night
$575 - $1595 week
Special Offer Mar 21 - Oct 1 20% off Septermber rentals excluding Labor Day - e ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort!! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the bes... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort!! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the bes... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer May 7 - Oct 1 20% Septermber rentals excluding Labor Day - ente ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 bath condo is 1300 sq. ft. It has a large livin... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 bath condo is 1300 sq. ft. It has a large livin... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Just steps from a private walkway to the beach, our townhouse overlooking the lake at Siesta Key is the ideal beach retreat for a family, group of ... Learn More
Location: Siesta Key, Florida, United States
Description: Just steps from a private walkway to the beach, our townhouse overlooking the lake at Siesta Key is the ideal beach retreat for a family, group of ... Learn More
Rates
$114 - $166 night
$529 - $1249 week
$114 - $166 night
$529 - $1249 week
Special Offer Mar 19 - Oct 1 20% off September rentals excluding Labor Day - en ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Enjoy the view of the white sand of Crescent Beach and the azure waters of the Gulf of Mexico from this lovely third floor 2 bedrooms, 2 baths gulf... Learn More
Location: Siesta Key, Florida, United States
Description: Enjoy the view of the white sand of Crescent Beach and the azure waters of the Gulf of Mexico from this lovely third floor 2 bedrooms, 2 baths gulf... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer Apr 27 - Oct 1 20% September rentals excluding Labor Day, enter p ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Crescent Beach, Siesta Key Florida! Newly renovated 2 bedroom, 2 bath unit. The unit is approx. 1000 sq. ft. has a large... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Crescent Beach, Siesta Key Florida! Newly renovated 2 bedroom, 2 bath unit. The unit is approx. 1000 sq. ft. has a large... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer Mar 12 - Oct 1 20% off September rentals exluding Labor Day- ente ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta key, Florida, United States
Description: DIRECT GULF FRONT, GROUND FLOOR! Siesta Key, Crescent Beach This unit is located in our southwest building. It is 1300 square feet. The unit is 2 b... Learn More
Location: Siesta key, Florida, United States
Description: DIRECT GULF FRONT, GROUND FLOOR! Siesta Key, Crescent Beach This unit is located in our southwest building. It is 1300 square feet. The unit is 2 b... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer May 21 - Oct 1 20% September rentals excluding Labor Day - enter ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida - Crescent Beach. This beautifully maintained complex is located on one of the finest beaches in cent... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida - Crescent Beach. This beautifully maintained complex is located on one of the finest beaches in cent... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer Feb 2 - Oct 1 20% September rentals excluding Labor Day - enter ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida, Crescent Beach - This NEWLY REMODELED, 2 bedrooms, 2 bath unit is appox. 1000 sq. ft. It has a larg... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida, Crescent Beach - This NEWLY REMODELED, 2 bedrooms, 2 bath unit is appox. 1000 sq. ft. It has a larg... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Find additional Vacation Rentals:
