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.
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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
Special Offer Apr 28 - Oct 1 20% Septermber rentals excluding Labor Day - enter ...
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: DIRECT GULF FRONT!! 2 Bedrooms, 2 bathrooms at Island House Beach Resort.4th Floor unit. The unit is 1300 sq. ft. King, 2 twins, sleeper. This bea... Learn More
Location: Siesta Key, Florida, United States
Description: DIRECT GULF FRONT!! 2 Bedrooms, 2 bathrooms at Island House Beach Resort.4th Floor unit. The unit is 1300 sq. ft. King, 2 twins, sleeper. This bea... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 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
Special Offer Apr 27 - Oct 1 20% off September rentals excluding Labor Day - en ...
Condo:
1 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
$187 - $281 night
$1309 - $1967 week
$187 - $281 night
$1309 - $1967 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 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 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, Crescent Beach! Professionally decorated in October 2011. This large 2 bedrooms, 2 bath unit is approx 1000 ... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort, Siesta key, Crescent Beach! Professionally decorated in October 2011. This large 2 bedrooms, 2 bath unit is approx 1000 ... Learn More
Rates
$160 - $241 night
$1120 - $1687 week
$160 - $241 night
$1120 - $1687 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
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 26 - Oct 1 20% September rentals excluding Labor Day - enter ...
Condo:
1 Bedroom, 2 Bathroom, Sleeps 4
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida - Southwest building, 3rd floor, One bed, 2 bath, King, 2 twins in den area. This unit is 1300 sq. f... Learn More
Location: Siesta Key, Florida, United States
Description: Island House Beach Resort - Siesta Key Florida - Southwest building, 3rd floor, One bed, 2 bath, King, 2 twins in den area. This unit is 1300 sq. f... Learn More
Rates
$187 - $281 night
$1309 - $1967 week
$187 - $281 night
$1309 - $1967 week
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
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
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 Feb 14 - 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 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 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
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 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 Mar 17 - 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 - Siesta Key Florida - Crescent Beach. This beautifully maintained complex is located on the widest part of one of the be... 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 the widest part of one of the be... Learn More
Rates
$206 - $314 night
$1442 - $2198 week
$206 - $314 night
$1442 - $2198 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
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Roll into the lap of luxury and enjoy a unit that?s still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in... Learn More
Location: Siesta Key, Florida, United States
Description: Roll into the lap of luxury and enjoy a unit that?s still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in... Learn More
Rates
$564 - $1750 week
$564 - $1750 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
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Featuring new living room furniture, and tile floors - life at this condo is luxe. Sleeping 6 people in 2 bedrooms, Jamaica Royale 91 is a great fa... Learn More
Location: Siesta Key, Florida, United States
Description: Featuring new living room furniture, and tile floors - life at this condo is luxe. Sleeping 6 people in 2 bedrooms, Jamaica Royale 91 is a great fa... Learn More
Rates
$119 - $350 night
$575 - $1595 week
$119 - $350 night
$575 - $1595 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 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
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: A large and comfortable condo, Siesta Key Gulf and Bay 207 rentals boasts 1,525 square feet of Mediterranean style. Enjoy gorgeous gulf views from ... Learn More
Location: Siesta Key, Florida, United States
Description: A large and comfortable condo, Siesta Key Gulf and Bay 207 rentals boasts 1,525 square feet of Mediterranean style. Enjoy gorgeous gulf views from ... Learn More
Rates
$564 - $1750 week
$564 - $1750 week
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