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 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
Featured
Special Offer Mar 28 - 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 best... 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 best... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 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% 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 23 - 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... 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 May 23 - 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
Special Offer Mar 16 - 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 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
Special Offer May 11 - 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! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best... 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 best... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer May 23 - 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 villa is approx. 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 - This large villa is approx. 1000 sq. ft. It has a large living area, dining area, ... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 week
Special Offer Mar 9 - 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. This attractive 2 bedroom, 2 bath villa is 1000 sq. ft. It has a large living room, ... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Crescent Beach, Siesta Key Florida. This attractive 2 bedroom, 2 bath villa is 1000 sq. ft. It has a large living room, ... 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: The moment you arrive at Gulf & Bay Bayside, you?ll appreciate the beauty, serenity, and charm of this ?old Key West? style village. Located on the... Learn More
Location: Siesta Key, Florida, United States
Description: The moment you arrive at Gulf & Bay Bayside, you?ll appreciate the beauty, serenity, and charm of this ?old Key West? style village. Located on the... Learn More
Rates
$119 - $350 night
$575 - $1595 week
$119 - $350 night
$575 - $1595 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 May 25 - 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 lovely unit 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 lovely unit 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 5
Location: Siesta Key, Florida, United States
Description: Overlooking Blind Pass Lagoon just a few blocks to Turtle Beach is our Siesta Key condo, Castaway Cove. Located in a small, friendly complex, it bo... Learn More
Location: Siesta Key, Florida, United States
Description: Overlooking Blind Pass Lagoon just a few blocks to Turtle Beach is our Siesta Key condo, Castaway Cove. Located in a small, friendly complex, it bo... Learn More
Rates
$95 - $250 night
$454 - $1395 week
$95 - $250 night
$454 - $1395 week
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
Special Offer Apr 17 - Oct 1 20% September rentals excluding Labor Day - enter ...
Villa:
2 Bedroom, 2 Bathroom, Sleeps 5
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Siesta Key, Florida, Crescent Beach. This large 2 bedrooms, 2 bath unit is appox. 1000 sq. ft. It has a large living are... 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 appox. 1000 sq. ft. It has a large living are... 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: Island House Beach Resort! Newly remodeled gulf view apartment. Brand new kitchen, bathrooms, wood and tile floors. The unit has a king, 2 twins, s... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Newly remodeled gulf view apartment. Brand new kitchen, bathrooms, wood and tile floors. The unit has a king, 2 twins, s... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 week
Special Offer May 16 - 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 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 - The 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
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 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
Special Offer Apr 27 - 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! Newly remodeled!! Crescent Beach, Siesta Key Florida! This attractive complex is located on the widest part of one of th... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort! Newly remodeled!! Crescent Beach, Siesta Key Florida! This attractive complex is located on the widest part of one of th... 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 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:
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
Special Offer Feb 2 - Oct 1 20% Septermber rentals excluding Labor Day - enter ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
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
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
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