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Siesta Key Beach Rentals <span>& Vacation Rentals - 416 Rentals Available</span>
1 / 24

Siesta Key Condo
1 BR / 1 BA / Sleeps 4 1 4 Min stay varies
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"Thank you for a wonderful week! The room was beautiful and Mary Ann and staff were all so accommodating to anything that you may need! We would highly recommend Siesta Palms to everyone! We are looking forward to coming back as soon as possible, ..."
- Beth and Larry, Hilton Head, SC
(4) Excellent (4 reviews)
1 / 29

Siesta Key Estate
7 BR / 6 BA / Sleeps 18 7 18 Min stay varies
Estate / 7 Bedrooms / Sleeps 18
7 bedrooms 6 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
"Beautiful beach house. Everything was thought about when they built & furnished this home. Great for family get togethers."
- Lisa Pacheco, GA
(1) Excellent (1 review)
1 / 21

Siesta Key Home
4 BR / 4 BA / Sleeps 12 4 12 Min stay varies
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"We have recently had the pleasure of renting a home on Peaceable way. The home was amazing very clean, well organized and the decor was exceptional. We rented the house with 2 other families the house was spacious and very accommodating to our needs...."
- Cathy Strauss, Buffalo New York
(3) Excellent (3 reviews)
1 / 30

Siesta Key Condo
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"My husband & I chose this condo on- line. It was immaculate, very nicely renovated, had a wonderful view of the boat docks and pool, and an owner who could not have been nicer. Midnight Cove II community is a gem. People & staff are friendly, the ..."
- Denise Chandler, Virginia
(10) Excellent (10 reviews)
1 / 19

Siesta Key Home
5 BR / 4 BA / Sleeps 12 5 12 14 night min stay
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"Beautiful home with so many added features! We are definitely coming back and staying at The Grand Canal!"
- Sharilyn Wright DeCrastos, Fishers, Indiana
(3) Excellent (3 reviews)
1 / 40

Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 14 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Great place! Everything was wonderful, beach was a short walk away. Love all the new addition to public beach. Pool was heated, we went swimming every day. Unit was very clean and comfortable, couldn't ask for a better place. Took the free taxi to village..."
- Margot Robbins, Altmar ny
(4) Excellent (4 reviews)
1 / 27

Siesta Key Villa
2 BR / 2 BA / Sleeps 6 2 6 5 night min stay
Villa / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We enjoy our stay, the rooms was amazing! ! ! evrething u need for whole family u have in the unit :)I recomended this place and for sure we will comeback here:)"
- Aliona Gonza, Chicago,il
(42) Excellent (42 reviews)
1 / 15

Siesta Key Home
4 BR / 4.5 BA / Sleeps 14 4 14 Min stay varies
Home / 4 Bedrooms / Sleeps 14
4 bedrooms 4.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
"We used this house as a work retreat and a celebration! Overall, the house was perfect. Plenty of space, the views were awesome, the living room was great for a work meeting (5 people). The balconies were great. A good location...away from the town..."
- Caroline Morello Gregorovic, NJ
(7) Excellent (7 reviews)
1 / 14

Siesta Key Condo
1 BR / 1 BA / Sleeps 4 1 4 7 night min stay
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"This was a great rental property for me and my son! We stayed the whole week to celebrate my birthday. This condo is located right across the street from Siesta Key public beach and it was just a quick walk. I loved that they already had beach chairs..."
- Anjuli Velazquez, Atlanta, GA, USA
(11) Excellent (11 reviews)
1 / 24

Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Condo was bright, clean, and spacious. Kitchen was so well equiped! Had four guests for dinner one night and we were all very comfortable. Grill down by the pool was great. First floor was very handy for us. I had no idea we could be so close to the..."
- Frank Krone, Rock Island IL
(24) Excellent (24 reviews)
1 / 41

Siesta Key Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"Our stay at Siesta Palms was great. The condo was very clean and up to date. We enjoyed the beautiful pool and proximity to the beach. The owners couldn't have been kinder or more accommodating. I highly recommend this condo."
- Lori Wiederkehr, New Haven, Indiana
(2) Excellent (2 reviews)
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Top 10 Activities in Siesta Key

Top 10 Activities in Siesta Key
A beach lover’s paradise, Siesta Key is packed with stunning stretches of sand and natural beauty. When you’re planning your next vacation to Siesta Key, don’t miss out on these top 10 activities.

Siesta Beach

Siesta Beach, one of the most popular beaches in the area, has plenty of soft sand for sunbathing and sparkling water for swimming. The sand here is 99 percent quartz, which means it stays cool even on warm days. There’s lifeguard protection year-round and a playground for young kids. Visitors will find plenty of parking spots here.

Ken Thompson Park

This waterfront park features boardwalks, boat access, and fishing areas. Cast your line from the pier, wander along the elevated boardwalk, or canoe through the mangrove forest at Ken Thompson Park. There’s no admission fee, and parking is available.

Ringling Museum of Art

For a dose of culture, look no further than the Ringling Museum of Art in Sarasota. With beautiful ...

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Three Day Itinerary: Siesta Key, FL

Three Day Itinerary: Siesta Key, FL
Siesta Key is a barrier island just off the coast of Sarasota, Florida. Famous for its soft white sand, Siesta Key is the ideal destination for vacationers who want to rest, relax, and enjoy a slower pace of life. From water rentals to fresh seafood, everything at Siesta Key revolves around the ocean.

Day 1: Treat Yourself at Siesta Key Village
A Siesta Key vacation is all about sun and sand, but don't hit the beaches ill-equipped. Head to Siesta Key Village for an indulgent day of shopping and dining. With 6,000 square feet of retail space, the Beach Bazaar has everything you could need for swimming, surfing, snorkeling, sunbathing, and otherwise enjoying your beach escape. Other shops in the village, such as Siesta Key Outfitters and Siesta Key University, offer other gear as well as beach-themed souvenirs for you to take home.

Stop at The Lobster Pot for a casual lunch with New England flair. Try a lobster roll or lobster bisque made with lobsters from Bar Harbor and ...

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About Siesta Key

If you're planning a vacation to this island paradise, you may want to consider Siesta Key vacation rentals. This beautiful barrier island spans eight miles just off the coast of Sarasota in the Gulf of Mexico. Resorts can be overcrowded and overpriced, but Siesta Key vacation home rentals are always private and generally quite affordable. This destination is known as a great romantic getaway, and there are plenty of cozy little cottages for two that will set the perfect mood for your honeymoon or other romantic rendezvous. Regardless of your lifestyle and budget, there is something here to meet your needs.

Things to do

If staying on dry land sounds like a bore, you'll find almost 50 miles of waterways and canals inside the island, not to mention the surrounding Gulf of Mexico and Sarasota and Roberts Bays. Many Siesta Key, FL vacation rentals provide boat docks, and boat rentals are available for you to get out and explore the waters. Other water sports are popular here as well, including fishing, snorkeling, parasailing, and sailboarding. If you'd rather not captain your own ship, plenty of local charter companies offer guided tours. Many of the local restaurants also offer temporary docking, so that you can go to dinner straight from your afternoon on the water. What better way to work up an appetite for some fresh seafood than a day spent in the sand, sun, and surf? We couldn't call it an "island paradise" if it didn't offer warm breezes, cool water, swaying palm trees, and some of the world's finest beaches, including Turtle Beach and Palmer Point Beach. Relaxing on the pure quartz beaches with family and friends is certainly a favorite pastime here, and visitors enjoy the charming beach hideaways and ample bird-watching opportunities. You might also spot some friendly dolphins and manatees dotting the surrounding gulf and bay waters.


As a top Florida vacation destination you can imagine that Siesta Key offers flawless weather all year round. With over 250 sunny days per year, and a July high of 91 degrees, you're pretty much guaranteed a vacation unspoiled by the elements no matter when you visit. Try booking your trip for the "shoulder season" away from peak times or school vacations to keep crowds at bay. Low humidity makes Siesta Key comfortable, as well as warm. 


If you visit the island during the beginning of May, the beach literally comes alive with figures made of sand during the island's unique sand sculpture contest that draws in world-class artists. Of course, anyone can try their hand at a sandcastle or sand sculpture any time of year. Take part in the Siesta Key drum circle on the Siesta Key public beach EVERY Sunday night. Beginning about an hour before sundown, instruments ranging from drums, flutes, guitars, shakers and cowbells create the circle. Be part of the audience, or participate with music and dance. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants. The Siesta Fiesta is in mid-April and celebrates local artisans while fostering a feeling of camraderie around the town. 


After a day out on the beach or screaming while parasailing you're likely to work up an appetite. A place like Senor Siesta. rated #1 on TripAdvisor for Siesta Key restaurants, could fit the bill. With delicious and affordable latin cuisine available such as the empanada appetizer, you will be happy you chose to eat there. If you're looking for a more European flavor, why not try out Bonjour French Cafe & Crepes? For dessert, you should grab a scoop or three at Ciao Gelato or Big Olaf Cremery. Lastly, for a more down home feel, eat at The Cottage Restaurant which has all types of classic American dishes made to perfection. You won't go hungry in Siesta Key, trust us.  

​All of this and more can be found within walking distance or a leisurely drive of Siesta Key vacation rentals, so start planning your trip today!