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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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: Aloha Kai is a 5 acre Oceanside (Gulfside) vacation retreat tucked away on the powder sand shores of Siesta Key. Featuring the largest heated outdo... Learn More
Location: Siesta Key, Florida, United States
Description: Aloha Kai is a 5 acre Oceanside (Gulfside) vacation retreat tucked away on the powder sand shores of Siesta Key. Featuring the largest heated outdo... 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: Just steps from a private walkway to the beach, our townhouse overlooking the beach Siesta Key is the ideal beach retreat for a family, group of fr... Learn More
Location: Siesta Key, Florida, United States
Description: Just steps from a private walkway to the beach, our townhouse overlooking the beach Siesta Key is the ideal beach retreat for a family, group of fr... Learn More
Rates
$114 - $166 night
$529 - $1249 week
$114 - $166 night
$529 - $1249 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
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
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
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
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime ho... Learn More
Location: Siesta Key, Florida, United States
Description: Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime ho... Learn More
Rates
$119 - $350 night
$575 - $1595 week
$119 - $350 night
$575 - $1595 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
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
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:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Siesta Key, Florida, United States
Description: Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated and has sensational sunset and Gulf views. Any q... Learn More
Location: Siesta Key, Florida, United States
Description: Siesta Key Florida House of Sun 307 rentals condos is very family-friendly, was recently renovated and has sensational sunset and Gulf views. Any q... Learn More
Rates
$146 - $450 night
$750 - $2095 week
$146 - $450 night
$750 - $2095 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
Special Offer May 23 - 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
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 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, 1 1/2 bath villa is appox. 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 appox. 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 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 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 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
Featured
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 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
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
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
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