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Siesta Key Holidays

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Where to stay in Siesta Key

Find the best Siesta Key areas for the activities you enjoy most. Learn more about Siesta Key
Learn more about Siesta Key
A vibrant building with a purple facade, a sign reading "Siesta," and a staircase leading to the entrance.

Siesta Key Village

This lively beach hub sits adjacent to Siesta Beach, one of America's top-rated shorelines. The compact village streets are lined with open-air restaurants, tiki bars, and colourful beach boutiques. Palm trees sway above outdoor dining patios where sunset cocktails flow freely. Travellers can easily explore the area on foot, enjoying live music that drifts from waterfront venues. The sugar-white sands and crystal-clear Gulf waters are just steps away. Shop for local crafts at the Siesta Key Farmers Market or simply relax in this quintessential beach paradise.

A sunset over a body of water with a dock and palm trees.

Bay Island

Bay Island offers a secluded paradise within Siesta Key with direct access to award-winning beaches. This exclusive waterfront community features luxury homes with private docks and stunning views of Sarasota Bay and the Gulf of Mexico. Pristine waters surround this affluent enclave where privacy comes standard. The island serves as a perfect base for exploring nearby attractions. Shell Beach and Lido Beach lie just minutes away by car. Travellers can easily visit Marie Selby Botanical Gardens or browse upscale shops at St. Armands Circle in neighbouring Sarasota.

A large, beige colonial-style building with columns, surrounded by palm trees and dense vegetation.
Photo by Michael Serrao
Open Photo by Michael Serrao

South Village

If you're spending some time in South Village, Safe Harbor Siesta Key and Crescent Beach are top sights worth seeing.

Aloha Kai

Aloha Kai offers a peaceful retreat on Siesta Key with direct access to world-renowned white sand beaches. This residential haven features luxury holiday rentals and condominiums set against the stunning backdrop of the Gulf of Mexico. The neighborhood's contemporary coastal architecture blends perfectly with manicured tropical landscapes. Walk along waterfront paths with views of both the Gulf and intracoastal waterways. The crystal-clear waters are ideal for swimming year-round. While quiet within its boundaries, Siesta Key Beach, Crescent Beach, and Siesta Key Village are just minutes away.

Bailey Hall

Bailey Hall might not have many top sights, but Siesta Key Beach and Lido Beach are two attractions nearby that you can check out.

Discover the most popular places to visit in Siesta Key

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 reviews)
Siesta Beach captivates with its unique quartz sand that stays cool even on hot days. Sink your toes into the powdery white shoreline while gazing at the clear turquoise waters that make this beach a favourite.

What to do in Siesta Key

HydroCats - 2 Hour CraigCat Sightseeing Tour

HydroCats - 2 Hour CraigCat Sightseeing Tour

S$188
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
See all activities in Siesta Key

Siesta Key Hotel Deals

Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
4.3 km from Siesta Key
9.4 out of 10, Exceptional, (5,702 reviews)
"Not a bad stay, but not great. The AC broke on check in day. So we were moved to a different room as nobody could fix it that day. But we couldn't stay in that room for more than a night, so we were moved again the next day. 3 moves in 2 days with 2 small kids isn't ideal. Also, although rooms are advertised as 1 bedroom, they are more accurately studios, with no actual separate bedroom, just an open room. The newer pool was nice, check-in and parking was easy."
The price is S$256
includes taxes & fees
23 Aug - 24 Aug
Tropical Beach Resorts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Siesta Key

Frequently Asked Questions

How much does a Siesta Key holiday package cost?

Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Siesta Key costs! Our packages make travel planning easier and save you more.

What are the cheapest months to go to Siesta Key?

September, October and November are the best times to look for cheap Siesta Key holiday packages. Travelling in less busy periods means you can typically find reduced prices on accommodation and flights.

How many days is enough for Siesta Key?

Dedicate around 4 days for your Siesta Key holiday to really take in all that makes this destination unique. Stroll around key neighbourhoods, including Central Sarasota and Siesta Key Village. Then head to the major sights like Shell Beach and Irma Beach. With a good itinerary, you can keep busy with room for some rest time too. Want to venture beyond Siesta Key? Consider an excursion or two.

Is it worth booking a holiday package to Siesta Key?

Boasting a host of highlights starting with its amazing coastal beaches, Siesta Key is a good holiday destination. Whether you'd like to discover attractions like Bay Island and Siesta Key Beach or take the road less traveled, you'll have plenty to see and do on your Siesta Key holiday.

How to find the best Siesta Key package deals?

Start your search for a Siesta Key package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Siesta Key package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Siesta Key escape off to a flying start.

Is it cheaper to book a Siesta Key holiday as a package?

You can enjoy significant savings on your next Siesta Key escape by booking a tailored holiday package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a holiday package to Siesta Key?

If you have your Siesta Key travel dates finalized, book as soon as you can to score some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.

How to plan a trip to Siesta Key?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favourite time of year and the available activities will also help you decide when to escape to Siesta Key.
  2. Calculate your budget: Make sure you have enough money to pay for everything from meals and transportation to airfares and activities. Your accommodation will likely be the largest expense during your trip to Siesta Key.
  3. Determine how many days away: Start by making a list of all the activities and attractions you want to experience in Siesta Key. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customised Siesta Key holiday package.

Book with confidence

Things to do in and around Siesta Key

Siesta Key is a delightful destination for beach and outdoor family vacations, offering a variety of activities. Enjoy a relaxing spa day, explore the stunning surroundings on a Siesta Key guided eco tour, or partake in fun tours that highlight the area's natural beauty. Additionally, the area features recreational spaces, resorts, and shopping centres, ensuring there's something for everyone to enjoy during their stay.

Shopping

In Siesta Key, visit the Siesta Key Farmers Market for local produce and crafts. Just 4.8km away, Gulf Gate Mall offers a variety of shops and entertainment. For a unique experience, Artisans' World Marketplace is 6.4km away, featuring local artisans' creations. If you're up for a drive, explore more nearby options.

Recreation

Experience the vibrant arts at Van Wezel Performing Arts Hall, where romance and culture intertwine. Enjoy the thrilling atmosphere at Ed Smith Stadium, perfect for sports enthusiasts. Unwind amidst nature at Stoneybrook Golf & Country Club, where outdoor activities and relaxation await in a serene environment.

Adventure

Explore the scenic trails at Sarasota BayWalk, a perfect spot for hiking only 6.4km from Siesta Key. For a thrilling tennis experience, visit Payne Park Tennis Center, located 8.0km away. Families can enjoy a fun-filled day at Astro Skate and Fun Center, situated 20.9km from Siesta Key.

Nightlife

In Siesta Key, Florida, the nightlife is vibrant and relaxed. Visit the lively bars and beach clubs along Ocean Boulevard, where you’ll find live music, dance floors, and beachfront cocktails. The atmosphere is friendly, making it perfect for socialising and enjoying the tropical evenings.

Find the best attractions in and around Siesta Key

Siesta Key offers a delightful destination for beach lovers and families alike, with attractions such as Siesta Beach and Siesta Key Public Beach. Visitors can enjoy outdoor activities and the vibrant atmosphere of urban parks and marinas. Whether you're seeking relaxation by the shore or engaging in city experiences, Siesta Key has something for everyone to enjoy amidst its stunning coastal scenery.

  • St. Armands Circle: A vibrant street just 4.8km from Siesta Key, St. Armands Circle is a delightful blend of boutique shops, fine dining, and lively atmosphere, perfect for leisurely strolls and people-watching.
  • Sarasota Opera House: Located 6.4km from Siesta Key, this historic opera house offers a rich cultural experience with its stunning architecture and captivating performances, embodying an enchanting mix of city charm and romantic ambience.
  • Siesta Key Beach: Situated within Siesta Key, this renowned beach is famous for its powdery white sand and crystal-clear waters, providing a quintessential beach vibe ideal for sunbathing, swimming, and relaxation.

Best time to go to Siesta Key

The best time to visit Siesta Key is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain.

Tips to save on your trip to Siesta Key

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Siesta Key.
  • Consider traveling to Siesta Key during the low season (August to September and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.