
Vacation rentals in Siesta Key
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Top-rated vacation rentals in Siesta Key
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Other great vacation rentals in Siesta Key

Last minute May ,house 2 Mil beach .Pets welcome
Wojciech was a great host - let us drop groceries off and check in early! The house was a 10 min drive to everything we had planned. We appreciated all of the beach amenities!

Second home vacation rental
Our stay at Leroy's place was just great. It was a great location. Easy to find. Easy check in. The place was clean. Kitchen was clean with all the amenities you need. Lots of clean linens ans towels. Bed was very comfortable. The air-conditioning was always cool and big ceiling fans. The bathroom was very clean and good size. The washer and dryer was an awesome thing to have. We loved the screened in back porch and enjoyed our evenings out there. The neighborhood was nice and great. No sirens ans loud cars or cars going by with loud music. It felt very respectful of one another. Leroy's place was not close to our venue, but it was such a nice stay for a great place, we would DEFINITELY stay again and highly recommend to others!

Cottage by the Sea
Pam and Bailey were super helpful and responsive. The place was incredible and the extra touches made it feel like home! Super private backyard and friendly neighbors. Would definitely stay there again!

HOME HOME ON THE RANCH. SARASOTA FL.
this was a great location.

Blue Heron Cottage - Anna Maria Island
The cottage is clean and roomy. There is enough space the pull out the couch without the living room feeling cramped. Lots of linens and towels were included, as well as beach gear. The outdoor shower was nice plus too! Gustav and Jose had clear instructions on check-in and check-out and were very responsive to my questions.

Luxury ~ Heated Pool ~ Games ~ near AMI, IMG, SRQ
Beautiful home, very clean, and very nicely decorated with all the modern amenities. The neighbourhood was great too, close to shopping and restaurants. The host was really welcoming and responsive. Overall super happy with our stay! Thank you!

Vacation home by Shasta Rd
The house was comfortable, and the kitchen was well stocked with all the dishes and cookware we needed. The location overlooking the pond is a highlight. The many kinds of birds that come onto the lawn and right onto the patio are fun to watch. As are the turtles and alligators that swim by all the time! The water in the area isn’t great, so there is a reverse osmosis filter in the kitchen for drinking and cooking water. But the water in the rest of the house isn’t filtered, so the water in the tub and toilets and laundry is a little amber colored. It didn’t affect our clothes in the laundry, and we used bottled water to brush teeth, so it was fine. Overall, we really enjoyed our stay, and would come back again!

Roxy’s Village 1
March 16-20, 2025 My friend and I went to Bradenton for a spring training baseball trip and stayed at Roxy's Place. It was great! Alex and Roxy were great in responding ahead of time and after we arrived. They even left us a nice bottle of wine! Thanks for having us! I would highly recommend!
Quick stats about vacation rentals in Siesta Key
Total rentals
1.8K properties
Total number of reviews
32K reviews
Family-friendly rentals
1.5K properties are a good fit for families
Pet-friendly rentals
330 properties allow pets
Rentals with a pool
1.4K properties have a pool
Rentals with dedicated workspaces
820 properties have a dedicated workspace
Your guide to Siesta Key
All About Siesta Key
The beaches on this barrier island in Sarasota have a luxurious feel, thanks to the pure white sand along its 13 kilometers of pristine coastline. On each of the island’s three main beaches — Siesta Beach, Crescent Beach, and Turtle Beach — the sand is almost exclusively composed of tiny quartz crystals, believed to have originated in the Appalachian Mountains millions of years ago. Digging your toes into it, you’ll notice the soft sand stays cool, even under the hot Florida sun. The beaches here fade into aquamarine surf, and as you watch the sunset over the Gulf of Mexico, you’ll come to appreciate why Siesta Key Beach is such a popular destination.
This beach town has a lively vibe, especially around its main hub, Siesta Key Village. At the core of the village on Ocean Boulevard, you’ll find a variety of local shops and open-air bars and restaurants giving you plenty to do here both on and off the sand.
The best time to stay in a vacation rental in Siesta Key
Siesta Key condo rentals can fill up in the springtime when the weather is warm and dry. This is when the area has the most festivals, too, with the Children’s Easter Party and Egg Hunt kick-starting the season in late March and the Siesta Fiesta arts and crafts festival in late April. The Amateur Sand Sculpting Contest in May invites you to try your hand at sculpting Siesta Key’s renowned quartz sand. But if you want to see the masters at work, consider visiting in November for the International Sand Sculpting Festival.
The summer months are another popular time for exploring options for Siesta Key villas for rent. The afternoons are often hot and humid, and there are typically more rain showers during this time of year. However, the long days are the main draw for many vacationers. As summer gives way to autumn, rain falls more steadily on the region until wintertime, when snowbirds arrive in search of mild winter weather.
Top things to do in Siesta Key
Siesta Beach
No trip to Siesta Key would be complete without visiting Siesta Beach, the most popular of the region’s three beaches. The white sand and warm water invite lounging and swimming, while volleyball courts offer a fun activity for groups. Concession stands with food and drink make it possible to spend the entire day at the water’s edge. There’s a longstanding tradition here on Sundays of winding down the week with a drum circle during sunset.
Siesta Village
A short walk from Siesta Beach will get you to Siesta Village, where you’ll find beach-style restaurants and tropical-themed bars. The bright-coloured shops, thatched-roof huts, and towering palm trees give the small district a vibrant atmosphere, while extra-wide sidewalks accommodate window shoppers and cyclists alike.
Point of Rocks
Point of Rocks is a beginner-friendly snorkelling area with shallow, calm water. This rocky sea wall located south of Crescent Beach hosts a myriad of sea life, including gentle manatees in the summertime. High tide is the best time to explore with a snorkel and fins, while low tide offers opportunities to examine tidal pools on land.
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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Amalie Arena
- Raymond James Stadium
- North Beach
- Vinoy Park
- Coquina Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Myakka River State Park
- Tropicana Field
- Van Wezel Performing Arts Hall
- Lakewood National Golf Club
- Splash Harbour Water Park
- Jannus Live
- Sunken Gardens
- Englewood Beach
- River Strand Golf and Country Club