Siesta Key Vacation Rentals in Florida
Our Siesta Key vacation rentals section includes the villa, home, cottage and condo rentals listed below.
Please click on the description to view more information about any of the vacation rentals in Siesta Key, Florida.
Our inventory of Siesta Key condo rentals changes frequently, so please bookmark this page and check back often. You may also be interested in Osprey (6 miles), Sarasota (6 miles), North Venice (10 miles), Nokomis (12 miles), and Longboat Key (12 miles) for additional vacation rental options.
| Results 1 - 25 of 28 | 1 2 Next |
Description
Type
Beds
Baths
Sleeps
Avg. Rate
Deluxe Townhouse(1- 4 Bedrooms)
This deluxe 3+ 1 bedroom townhouse is located in the heart of Siesta Village... Just a few steps to all the shops and restauran...
This deluxe 3+ 1 bedroom townhouse is located in the heart of Siesta Village... Just a few steps to all the shops and restauran...
Villa
4
3.5
12
$1,193/wk
Siesta Key 2 Bedroom Water View
Excelsior 307 is located in Siesta Key, Florida, and features vaulted ceilings and partial views of the bay. This is a Gulf...
Excelsior 307 is located in Siesta Key, Florida, and features vaulted ceilings and partial views of the bay. This is a Gulf...
Condo
2
2
6
$709/wk
$2,292/mth
$2,292/mth
Luxury Siesta Key Beachfront Condo
One of Siesta Keys newest complexes, (Spring 2006), Crescent Siesta Key offers luxury living at its best. This spacious...
One of Siesta Keys newest complexes, (Spring 2006), Crescent Siesta Key offers luxury living at its best. This spacious...
Condo
3
3
6
$3,130/wk
$11,145/mth
$11,145/mth
*sun, Sand & Save 25% To 50%*
*Sun, Sand & SAVE 25% to 50%* at Siesta Breakers #603, an Updated, Gulf Side, Beach Condo at Siesta Breakers Resort Condom...
*Sun, Sand & SAVE 25% to 50%* at Siesta Breakers #603, an Updated, Gulf Side, Beach Condo at Siesta Breakers Resort Condom...
Condo
2
2
6
$1,090/wk
$3,798/mth
$3,798/mth
*sun, Sand & Save 25% To 50%*
*Sun, Sand & SAVE 25% to 50%* at Midnight Cove #532, an Updated, Bayside Condo with all Gulf Side Beach Amenities Access...
*Sun, Sand & SAVE 25% to 50%* at Midnight Cove #532, an Updated, Bayside Condo with all Gulf Side Beach Amenities Access...
Condo
2
1.5
6
$689/wk
$2,483/mth
$2,483/mth
Tropical Paradise Home on Siesta Key
Nestled in a tropical paradise, this contemporary 3/2 home with private lanai and pool on a quiet street is a true island...
Nestled in a tropical paradise, this contemporary 3/2 home with private lanai and pool on a quiet street is a true island...
Home
3
2
6
$1,429/wk
Luxury Siesta Key Beachfront Home
Luxury Siesta Key Beachfront Home is currently booked from February 1, 2009 through April 11, 2009. This charming 2 Bedroom,...
Luxury Siesta Key Beachfront Home is currently booked from February 1, 2009 through April 11, 2009. This charming 2 Bedroom,...
Home
2
2.5
6
$2,624/wk
$8,248/mth
$8,248/mth
Siesta Key 1st floor, Resort Condo
“Palm Bay Club” is a resort community stretching across the Island from the Bay to the Gulf. The Complex’s amenities...
“Palm Bay Club” is a resort community stretching across the Island from the Bay to the Gulf. The Complex’s amenities...
Condo
2
2
6
$193/nt
$1,286/wk
$4,630/mth
$1,286/wk
$4,630/mth
Siesta Key Vacation Luxury Private
Siesta key beach, great gulf views from your private 3000 s.f. house just steps away on private access to the world famous...
Siesta key beach, great gulf views from your private 3000 s.f. house just steps away on private access to the world famous...
Home
3
3.5
6
$1,661/wk
$5,215/mth
$5,215/mth
Crescent Beach Luxury Condo directly
Luxury 2 bedroom 2 bathroom private condominium, Unit 204 at the El Presidente in Siesta Key is directly on the world's most...
Luxury 2 bedroom 2 bathroom private condominium, Unit 204 at the El Presidente in Siesta Key is directly on the world's most...
Condo
2
2
6
$1,375/wk
Bay Tree Club - Heaven on the Bay!
2Bed/2Bath Condo Just renovated/modernized with the latest & best kitchen appliances, furniture, pictures and other...
2Bed/2Bath Condo Just renovated/modernized with the latest & best kitchen appliances, furniture, pictures and other...
Condo
2
2
6
$953/wk
$3,333/mth
$3,333/mth
Siesta Key, Florida Crescent Beach
Turn key Ground floor corner apartment with windows on three sides gives the apartment a wonderful open feeling. The unit...
Turn key Ground floor corner apartment with windows on three sides gives the apartment a wonderful open feeling. The unit...
Condo
2
2
4
$3,084/mth
Siesta Best Villa and Sunset
If you are looking for a perfect get away with a fiesta feeling, then this is the perfect place for you and your family....
If you are looking for a perfect get away with a fiesta feeling, then this is the perfect place for you and your family....
Villa
2
2
6
$1,032/wk
Beachfront Penthouse Condo at Siesta
Condo #408 is a spacious 1000 sq. ft., light and airy one- bedroom deluxe condo at Sunset Royale on Siesta Key and is special...
Condo #408 is a spacious 1000 sq. ft., light and airy one- bedroom deluxe condo at Sunset Royale on Siesta Key and is special...
Condo
1
1
4
$1,109/wk
All Rates Will Be Discounted By
Deb's Dream Villa d5 is gulfside at beautiful Siesta Key, a barrier island, in Sarasota, Florida. There are no streets...
Deb's Dream Villa d5 is gulfside at beautiful Siesta Key, a barrier island, in Sarasota, Florida. There are no streets...
Villa
2
2
6
$148/nt
$1,043/wk
$1,043/wk
Excelsior Beach to Bay Condo
Excelsior Beach To Bay unit 304 is located on the bay side of Siesta Key. With a beautiful garden / pond view this 2 bedroom...
Excelsior Beach To Bay unit 304 is located on the bay side of Siesta Key. With a beautiful garden / pond view this 2 bedroom...
Condo
2
2
6
$947/wk
** Private Villa~Famous Siesta
If you are looking for a vacation condo rental in Siesta Key, Florida for your Florida holidays and family beach vacation...
If you are looking for a vacation condo rental in Siesta Key, Florida for your Florida holidays and family beach vacation...
Villa
2
1
6
$942/wk
20% off: Beautiful condo in Siesta
Beautiful Condo on Siesta Key! Two Bedroom, Two Bath condo sleeps six - gorgeous garden view on the bayside of the property....
Beautiful Condo on Siesta Key! Two Bedroom, Two Bath condo sleeps six - gorgeous garden view on the bayside of the property....
Condo
2
2
6
$1,029/wk
Three bedroom house directly on
Our house is a one month minimum rental with no exceptions. Tiffany Sands is a group of 9 townhouses directly on Crescent...
Our house is a one month minimum rental with no exceptions. Tiffany Sands is a group of 9 townhouses directly on Crescent...
Home
3
3.5
7
$1,852/wk
$5,732/mth
$5,732/mth
4 BR Island Getaway
Island Home on beautiful Siesta Key. Its location is perfect for exploring the Sarasota Area. Minutes from beautiful downtown...
Island Home on beautiful Siesta Key. Its location is perfect for exploring the Sarasota Area. Minutes from beautiful downtown...
Home
4
2
6
$1,952/mth
Siesta Key, Crescent Beach,
Siesta Key beach- side, 2 bedroom 2 bath completly redone condo. Located 200 feet to "Worlds Famous Siesta Key Beach."...
Siesta Key beach- side, 2 bedroom 2 bath completly redone condo. Located 200 feet to "Worlds Famous Siesta Key Beach."...
Condo
2
2
6
$1,011/wk
Beach Rental Siesta Key 1 & 2br
#2 rated Beach in America! Your ideal choice for Sarasota beach- front condominium accommodations, the Casa Blanca on...
#2 rated Beach in America! Your ideal choice for Sarasota beach- front condominium accommodations, the Casa Blanca on...
Villa
2
1
6
$132/nt
$921/wk
$921/wk
Siesta Key Beach Cottages Sarasota
The Beach Place is a small resort of five tropical garden beach cottages located at Siesta Key Beach - 30 seconds...
The Beach Place is a small resort of five tropical garden beach cottages located at Siesta Key Beach - 30 seconds...
Cottage
1
1
6
$915/wk
Beachfront Siesta Key, Florida
Find your vacation getaway on the island paradise of Siesta Key, Florida! Our condo is located on beautiful Crescent Beach,...
Find your vacation getaway on the island paradise of Siesta Key, Florida! Our condo is located on beautiful Crescent Beach,...
Condo
2
2
6
$1,325/wk
Siesta Key Lakeside Villa near Beach
Surrounded by tropical garden our secluded Villa is situated in a quiet cul de sac edged on two sides by Lake Nancy. The...
Surrounded by tropical garden our secluded Villa is situated in a quiet cul de sac edged on two sides by Lake Nancy. The...
Villa
3
2
7
$1,250/wk
$4,125/mth
$4,125/mth