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Siesta Key

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Vacation Rentals in Siesta Key, FL

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Siesta Key Vacation Rentals

Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

Lions, Tigers & Circuses

When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

Gardens & Aquariums

Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

Locomotives & Science

Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theater, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

History & Baseball

From your money-saving Siesta Bay vacation rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.

 
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
United States, Florida, Siesta Key Holiday Rentals
Steps away FROM the Gulf's crystal clear waters - Villa 34
Slideshow
4 of 5 stars 2 reviews
  • Villa
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
152 AUD - 238 AUD
Week:
1,063 AUD - 1,667 AUD
Minimum rental - 3 nights
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United States, Florida, Siesta Key Holiday Rentals
Updated villa w/ free wifi & full amenities - Villa 33
Slideshow
4 of 5 stars 2 reviews
  • Villa
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
159 AUD - 247 AUD
Week:
1,114 AUD - 1,731 AUD
Minimum rental - 3 nights
Check availability
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United States, Florida, Siesta Key Holiday Rentals
Beachfront Penthouse on Siesta Key! - 2 Month Min.
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
1,539 AUD - 2,053 AUD
Month:
2,566 AUD - 6,158 AUD
Minimum rental - 30 nights
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Also consider
Bay Views...
184 AUD - 241 AUD / night
3 Bedrooms, sleeps 6
2 Bathrooms
2/2 most...
919 AUD - 1,842 AUD / week
2 Bedrooms, sleeps 6
2 Bathrooms
Fabulous Condo...
115 AUD / night
2 Bedrooms, sleeps 6
1 Bathroom
Luxury...
175 AUD / night
2 Bedrooms, sleeps 6
2 Bathrooms
Amazing Gulf...
204 AUD / night
2 Bedrooms, sleeps 4
2 Bathrooms
United States, Florida, Siesta Key Holiday Rentals
Siesta Key private beach access
Slideshow
4 of 5 stars 1 review
  • Villa
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
154 AUD
Week:
1,078 AUD - 1,899 AUD
Month:
3,464 AUD - 6,055 AUD
Minimum rental - 1 week
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United States, Florida, Siesta Key Holiday Rentals
Siesta Key 2/1 Updated Modern/Contemporary Decor
Slideshow
4 of 5 stars 3 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Special offer details »
Night:
128 AUD - 231 AUD
Week:
770 AUD - 1,334 AUD
Month:
2,360 AUD - 3,900 AUD
Minimum rental - 5 nights
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United States, Florida, Siesta Key Holiday Rentals
Enjoy Quiet Turtle Beach & View Sunsets From Lanai
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
164 AUD
Week:
1,149 AUD - 1,791 AUD
Month:
3,908 AUD - 6,804 AUD
Minimum rental - 1 week
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United States, Florida, Siesta Key Holiday Rentals
1 Min. #1 Siesta beach Gulf Views-Luxury Home
Slideshow
4.5 of 5 stars 9 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
359 AUD - 462 AUD
Week:
2,771 AUD - 3,181 AUD
Month:
9,750 AUD - 11,289 AUD
Minimum rental - 3 nights
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United States, Florida, Siesta Key Holiday Rentals
BAY TREE GETAWAY ON SIESTA KEY
Slideshow
4.5 of 5 stars 4 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
924 AUD - 1,026 AUD
Minimum rental - 2 weeks
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United States, Florida, Siesta Key Holiday Rentals
Beachfront Condo Siesta Key : Fall Specials!!!
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
1,040 AUD - 1,473 AUD
Minimum rental - 1 week
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United States, Florida, Siesta Key Holiday Rentals
Enjoy your Siesta
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
103 AUD - 133 AUD
Week:
667 AUD - 790 AUD
Month:
1,847 AUD - 2,258 AUD
Minimum rental - 6 nights
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United States, Florida, Siesta Key Holiday Rentals
*Sun, Sand & SAVE 25% to 55%* Siesta Breakers #603
Slideshow
4.5 of 5 stars 13 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
889 AUD - 1,647 AUD
Month:
3,109 AUD - 5,931 AUD
Minimum rental - 1 week
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United States, Florida, Siesta Key Holiday Rentals
Palm Bay Club  Private Beach 3 min. - Pool, jacuzi
Slideshow
4.5 of 5 stars 6 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
169 AUD - 257 AUD
Week:
872 AUD - 1,642 AUD
Month:
3,489 AUD - 5,337 AUD
Minimum rental - 3 nights
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United States, Florida, Siesta Key Holiday Rentals
*Enjoy #1 BEACH in USA, Superb Sunsets, WiFi, Pool
Slideshow
4.5 of 5 stars 22 reviews
  • Villa
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Owner
EMAIL OWNER
Special offer details »
Night:
120 AUD - 164 AUD
Week:
842 AUD - 1,149 AUD
Minimum rental - 5 nights
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United States, Florida, Siesta Key Holiday Rentals
Spacious villa a stroll from Florida Gulf beaches - Villa 32
Slideshow
4 of 5 stars 2 reviews
  • Villa
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
159 AUD - 247 AUD
Week:
1,114 AUD - 1,731 AUD
Minimum rental - 3 nights
Check availability
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United States, Florida, Siesta Key Holiday Rentals
2-Bedroom- Upscale- Gulf Front Retreat- Siesta Key
Slideshow
4.5 of 5 stars 11 reviews
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Special offer details »
Week:
1,175 AUD - 1,688 AUD
Minimum rental - 1 night
Check availability
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United States, Florida, Siesta Key Holiday Rentals
Attract 2BR condo w/ free wifi & beach access - Villa 15
Slideshow
4 of 5 stars 1 review
  • Villa
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
159 AUD - 247 AUD
Week:
1,114 AUD - 1,731 AUD
Minimum rental - 3 nights
Check availability
Show on map

Siesta Key Holiday Rental Advice

condo walking distance from village and beach
Posted by Beachtime, 26 Feb 2012
... where travelers must rely on vacation rentals for their accommodations and most that I know understand customer service and understand that accommodating is an important part of accommodations. I have private messaged you on a suggestion for an ideal vacation rental that is very close to Siesta Village and directly ... more
Wheelchair Accessible Condo/House
Posted by landroverOntario, 24 Apr 2012
... 1/2 bathroom, wheelchair accessible vacation rental in Siesta Key area for Apr/May 2013. Bathroom must be large enough to accommodate the turning radius of a wheelchair, must have a roll-in shower, sufficient room for wheelchair to pull up beside toilet and no cupboards under sink so wheelchair ... more
Hotels in Siesta Key
Posted by baglab1, 16 Apr 2012
SRQgirl knows her stuff!!! We stayed @Midnight Cove... there are gulfside and bayside units. Some units are available on the vacation rental websites and @www.midnightcove.com. Looks like some would fit your budget. We really enjoyed this complex. Everything was also close whether walking or driving. Have fun! ... more
Siesta key last minute rental
Posted by Bluenose2010, 29 Mar 2012
Looking for a one bedroom on the ocean or intercoastal from April 4- April 10th 2012. Close to Palm Bay Club or Aloha Kai. Prefer not to be on ground floor. Two non smoking mid aged Canadians looking for a last minute vacation rental. ... more
Anything like Crescent Towers ...
Posted by siestales51, 7 Mar 2012
... want to browse through the vacation rental section of trip advisor called Flip Key, verified reviews and there are a number of step out to the sand condos on there. Island House has a couple that have good reviews, 1N or 1S in the towers are both ground floor beachfront ... more
Condo Contracts - substitution of a different condo
Posted by siestales51, 3 Feb 2012
I would also recommend Siesta Sunset Royale, very close beach and to village, but not right in the village. Lovely rooms, completely remodeled, family friendly. Nice skydeck with views. You can find reviews for them under specialty lodging on trip advisor or under Flip Keys vacation rental section of TA. ... more
What condo complex to stay at?
Posted by Beachtime, 3 Feb 2012
There are many options for vacation rentals in 2013, but keep in mind that Easter falls on March 31 in 2013. Reserve your vacation rental ASAP and guarantee your rates. 2013 rentals will be at a premium. ... more
Please help narrow down our choices....
Posted by siestales51, 19 Jul 2011
... this year called Siesta Sunset Royale - you will find reviews under flip key the vacation rental section of trip advisor for this rental. Walking distance to Siesta Village, less than a minute to the beach, only 7 apartments, nice pool and the penthouse has lovely views of Siesta Key Beach ... more
Villa rental for 12+
Posted by siestales51, 30 Aug 2011
... bedrooms in each. I believe they are connected. I have not been inside but photos look great and I have been outside many times, nice. Information on both can be found in the vacation rental section of trip advisor for Siesta Key, just type the names in the search box ... more
siesta sunset royale rental
Posted by siestales51, 30 May 2011
... the details that make a vacation rental special ... ... all the way to downtown on the other. There are plenty of Flip Key verified reviews for Siesta Sunset Royale on the vacation rental section of Trip Advisor, if you type the name in the search box the reviews should come up ... more