How much does a Siesta Key vacation package cost?

Offering great value package deals from $448 on Expedia, you'll be surprised at how little a vacation to Siesta Key costs! Our packages make travel planning easier and save you more.

What are the cheapest months to go to Siesta Key?

You can typically find reduced prices and greater availability in September, October and December. Take a look at our cheap Siesta Key vacation packages and you could score some excellent off-season deals.

How many days is enough for Siesta Key?

With around 4 days, you'll have enough time to enjoy popular neighborhoods like Central Sarasota and Newtown during your Siesta Key vacation. Remember to also add Shell Beach and Irma Beach to your sightseeing list. Up for some more adventures? Consider exploring outside of Siesta Key on day trips and tours.

Is it worth booking a vacation package to Siesta Key?

Well known for its coastal beaches and home to popular attractions like Siesta Key Beach , a Siesta Key vacation is bound to impress. Another top sight worth exploring? Don't miss Crescent Beach .

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 vacation as a package?

You can enjoy significant savings on your next Siesta Key escape by booking a tailored vacation 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 vacation 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?

Choose your dates: The things you'd like to do in Siesta Key and your preferred season can help you decide when to travel. Plan your budget wisely: Besides the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Siesta Key. Organize your Siesta Key getaway with Expedia's trip planning tool : Look for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Siesta Key together. Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Siesta Key. Then, estimate how long you'll need for each, along with any travel time. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Siesta Key vacation package. Add on excursions and experiences: Take a look at our travel guide to find some awesome things to do in Siesta Key . Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Siesta Key vacation packages?

If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Siesta Key trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

Siesta Key Vacation Packages 2025/2026 from $355

Things to do in and around Siesta Key

Siesta Key offers a perfect blend of beach and outdoor activities for families. Visitors can enjoy kayaking tours, play tennis at local courts, and explore hidden beaches. Don't miss the chance to shop at popular mall centers or unwind at resorts. For a memorable experience, consider the best vacation packages and create a sightseeing list to discover the area’s natural beauty and attractions.

Shopping

For a delightful shopping experience in Siesta Key, visit the Siesta Key Farmers Market for local goods. Gulf Gate Mall, 3 miles away, offers a variety of shops and entertainment. If you're up for a drive, check out Artisans' World Marketplace, located 4 miles from Siesta Key.

Recreation

At Van Wezel Performing Arts Hall, immerse yourself in captivating performances that blend culture and romance, just 5 miles from Siesta Key. Ed Smith Stadium, 6 miles away, offers an energetic atmosphere for sports enthusiasts, while Gulf Gate Golf Club, 4 miles from Siesta Key, invites you to enjoy outdoor golfing adventures.

Adventure

Explore the scenic Sarasota BayWalk, a beautiful hiking trail 4 miles from Siesta Key, offering breathtaking views and outdoor adventure. For family fun, visit the Astro Skate and Fun Center, an arcade 13 miles away. Additionally, enjoy tennis at the Payne Park Tennis Center, located 5 miles from Siesta Key.

Nightlife

Siesta Key's nightlife offers a vibrant atmosphere with beachfront bars like the Siesta Key Oyster Bar and lively venues such as The Beach Club. Enjoy live music, dancing, and delicious cocktails while soaking in the laid-back charm of this beautiful coastal paradise.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Siesta Key

Siesta Key, Florida, is an ideal destination for beach lovers and families seeking outdoor adventures. Visitors can explore popular attractions like Siesta Key Beach, Siesta Key Palms, and the local marina, while enjoying the area's urban parks. Whether you're looking for a relaxing day by the water or a vibrant city experience, Siesta Key offers a variety of activities that cater to all types of travelers.

Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a relaxed atmosphere perfect for sunbathing, swimming, and beachcombing. The stunning sunsets provide a picturesque backdrop, making it an idyllic spot for relaxation and fun.
St. Armands Circle: A vibrant shopping and dining destination, St. Armands Circle is filled with unique boutiques, galleries, and restaurants. Enjoy a leisurely stroll around the circle, where you can savor delicious cuisine while soaking in the lively city vibes.
Marina Jack: This bustling marina provides opportunities for outdoor adventures, including boat rentals and fishing charters. With beautiful waterfront views, it's a great place to enjoy fresh seafood and experience the local beach culture.

Best time to go to Siesta Key

The best time to visit Siesta Key can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Siesta Key falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Siesta Key falls in January, visitor numbers are moderately high and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	62.6°F (17.0°C)	Light Rain	Mostly Sunny	Moderately High	Average
February	65.1°F (18.4°C)	No Rain	Mostly Sunny	Average	Slightly High
March	68.0°F (20.0°C)	No Rain	Sunny	Moderately High	Slightly High
April	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	77.7°F (25.4°C)	Light Rain	Mostly Sunny	Average	Average
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny	Average	Average
July	82.9°F (28.3°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
September	81.5°F (27.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	77.2°F (25.1°C)	Light Rain	Mostly Sunny	Moderately Low	Average
November	70.7°F (21.5°C)	No Rain	Mostly Sunny	Moderately Low	Slightly Low
December	66.6°F (19.2°C)	No Rain	Mostly Sunny	Moderately Low	Average

Tips to save on your trip to Siesta Key

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically August to September and November) for more affordable package holidays to Siesta Key.
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.