Siesta Key Vacation Rentals, Apartments, & More
Siesta Key (216) Filter Cancel

1-50 of 216 Siesta Key Rentals

Sort: Relevance
1  2  3  4  5 
1  2  3  4  5 
page 1 of 5

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 ...

Read more

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 ...

Read more

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 ...

Read more