Siesta Key Vacation Rentals
81 Siesta Key Vacation 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.
SW Gulf Coast Top Cities
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: Island House Beach Resort - Siesta Key - Crescent Beach. This beautifully maintained complex is located on the widest part of one of the best beach... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key - Crescent Beach. This beautifully maintained complex is located on the widest part of one of the best beach... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Featured
Special Offer Mar 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 bright spacious villa is approx. 1000 sq. ft. and has all the comforts and lux... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida, Crescent Beach. This bright spacious villa is approx. 1000 sq. ft. and has all the comforts and lux... Learn More
Rates
$152 - $232 night
$1064 - $1624 week
$152 - $232 night
$1064 - $1624 week
Featured
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 Mar 12 - Oct 1 20% Septermber rentals excluding Labor Day - ente ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Crescent Beach on the Gulf of Mexico. This beautifully maintained complex is located on the widest part of one of the best beaches on the west coas... Learn More
Location: Siesta Key, Florida, United States
Description: Crescent Beach on the Gulf of Mexico. This beautifully maintained complex is located on the widest part of one of the best beaches on the west coas... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer Mar 12 - Oct 1 20% September rentals excluding Labor Day - enter ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Crescent Beach, Siesta Key Florida. 2nd Floor unit, 2 bedrooms, 2 baths. This beautifully maintained complex is located... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Crescent Beach, Siesta Key Florida. 2nd Floor unit, 2 bedrooms, 2 baths. This beautifully maintained complex is located... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer Mar 12 - Oct 1 20% off September rentals excluding Labor Day - en ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
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 best beaches in Florida.... 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 best beaches in Florida.... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer Mar 19 - 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 villa is approx. 1000 sq. ft. It has a large living a... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft. It has a large living a... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 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 Mar 14 - 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 large 2 bedroom, 2 bath villa is 1000 sq. ft. It has a large living area, din... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida - Crescent Beach. This large 2 bedroom, 2 bath villa is 1000 sq. ft. It has a large living area, din... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer May 9 - 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. Newly remodeled 2 bedrooms, 2 baths villa located on the finest beach in Florida. This unit is 2 bed... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta Key Florida. Newly remodeled 2 bedrooms, 2 baths villa located on the finest beach in Florida. This unit is 2 bed... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer Mar 30 - Oct 1 20% Septermber 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 large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft. It has a large living ... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft. It has a large living ... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer Feb 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 2 bedrooms, 2 bath villa is appox. 1000 sq. ft. It has a large living a... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is appox. 1000 sq. ft. It has a large living a... 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 excluding Labor Day - en ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key, Crescent Beach. This luxury apartment is located on 280 ft. of beautiful Crescent Beach. Island House has a... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key, Crescent Beach. This luxury apartment is located on 280 ft. of beautiful Crescent Beach. Island House has a... 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 Mar 12 - 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. Completly remodeled January 2011!! This 1000 sq. ft villa is 2 bedrooms, 2 baths an... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key Florida - Crescent Beach. Completly remodeled January 2011!! This 1000 sq. ft villa is 2 bedrooms, 2 baths an... 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 6
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort- Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft. It has 2 bedrooms, 2 baths, large living a... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort- Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft. It has 2 bedrooms, 2 baths, large living a... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 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 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!! Crescent Beach, Siesta Key Florida! Direct Gulf Front - Panoramic Views. This beautifully mainained complex is located ... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort!! Crescent Beach, Siesta Key Florida! Direct Gulf Front - Panoramic Views. This beautifully mainained complex is located ... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 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 May 18 - 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 1000 sq. ft. It has a large living area, ful... 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 1000 sq. ft. It has a large living area, ful... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 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 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
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf & Bay Club #409 is guaranteed bliss. Confirmed ... Learn More
Location: Siesta Key, Florida, United States
Description: Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf & Bay Club #409 is guaranteed bliss. Confirmed ... Learn More
Rates
$451 - $1750 week
$451 - $1750 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:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: An idyllic ocean side condo perfect for energetic kids or families seeking added privacy, Siesta Dunes Beach 38A is your perfect vacation rentals c... Learn More
Location: Siesta Key, Florida, United States
Description: An idyllic ocean side condo perfect for energetic kids or families seeking added privacy, Siesta Dunes Beach 38A is your perfect vacation rentals c... Learn More
Rates
$119 - $350 night
$575 - $1595 week
$119 - $350 night
$575 - $1595 week
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