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A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

Siesta Key Vacation Packages

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The Latest Siesta Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 9 - Oct 13

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    4 nights
    3.0 star property
    9.2/10 - Wonderful (557 reviews)
    "Loved this property. Perfect place for a quiet vacation. Sits right on the beach and the views were amazing. The owner and staff were very nice. Booked through Expedia and it was a little expensive but would stay there again."
    Reviewed July 17, 2026
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,759
    CA $1,090
    per traveller
    found 17 hours ago
    Cedar Cove Resort and Cottages
  • 2 bedrooms, memory foam beds, in-room safe, blackout drapes
    Sept 17 - Sept 22

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,090 reviews)
    "Wonderful place to stay. Only wish there was a more comfortable chair in the living room area. Clean, excellent space to relax and enjoy your time at the beach. Would be nice to have a fan on the balcony for those very hot nights."
    Reviewed July 17, 2026
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,812
    CA $1,203
    per traveller
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • Living area
    Sept 3 - Sept 8

    CW Hotel + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    10/10 - Exceptional (6 reviews)
    "We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!"
    Reviewed July 8, 2026
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,756
    CA $1,220
    per traveller
    found 21 hours ago
    CW Hotel
  • Grand Suite, 3 Bedrooms, Ocean View | Terrace/patio
    Sept 27 - Oct 2

    The Avalon Club + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (572 reviews)
    "Just the parking fee is expensive I paid like almost 300 for two cars in 2 days"
    Reviewed July 17, 2026
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,688
    CA $1,174
    per traveller
    found 1 day ago
    The Avalon Club
  • Outdoor pool, pool umbrellas, sun loungers
    Sept 17 - Sept 22

    Wyndham Grand Clearwater Beach + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (3,542 reviews)
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,952
    CA $1,388
    per traveller
    found 10 hours ago
    Wyndham Grand Clearwater Beach

Where to stay in Siesta Key

Find the best Siesta Key areas and neighborhoods 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

While visiting South Village, you might make a stop by sights like Siesta Key Marina and Crescent Beach.

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 vacation 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

When in Bailey Hall, you can plan a visit to Siesta Key Beach and Lido Beach, some noteworthy sights in the nearby area.

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)
The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.

What to do in Siesta Key

Mangroves, Manatees & a Hidden Beach Kayak Tour (Siesta Key)

Mangrove Tunnel & Manatee Kayak Eco-Tour

CA $84
per adult
94% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-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, (5,670 reviews)
The price is CA $213
CA $278 total
includes taxes & fees
Aug 9 - Aug 10
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 vacation package cost?

You'll find cheap prices from CA $1,090 on Expedia for your Siesta Key break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Siesta Key costs.

What are the cheapest months to go to Siesta Key?

You can usually find lower rates and better availability in September, October and November. Check out our cheap Siesta Key vacation packages and you could get some great off-season deals.

How many days is enough for Siesta Key?

Siesta Key vacations come in all shapes and sizes, but to really sink your teeth into this destination, we'd say 4 days is about right. This will mean you can visit top sights like Lido Beach and St. Armands Circle along with hidden gems. Don't forget to visit neighbourhoods such as Central Sarasota and Siesta Key Village either. If you're smart with your time, you can even allow for a day trip or two from Siesta Key too.

Is it worth booking a vacation package to Siesta Key?

Well known for its coastal beaches and home to leading attractions like Bay Island, a Siesta Key vacation is sure to impress. Another top sight to visit? Don't miss Siesta Key Beach.

How to find the best Siesta Key package deals?

Begin your search for a Siesta Key package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Siesta Key package deal right away, just switch up 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 getaway 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 getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Siesta Key?

If you have your Siesta Key travel dates locked in, book early to bag some terrific deals. With Expedia, you can often reserve some flights up to one 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. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Siesta Key.
  2. Budget wisely: In addition to the price of your stay, you should factor in other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Siesta Key.
  3. Decide your trip length: Consider how long you'd like to spend exploring Siesta Key. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Siesta Key vacation package that brings all your bookings together.

Book with confidence

Things to do in and around Siesta Key

Siesta Key, Florida, is perfect for family vacations, offering stunning beaches and outdoor activities. Visitors can enjoy a variety of adventure activities, explore area attractions, and indulge in golf vacations. The destination features recreational areas, resorts, and shopping mall centres, ensuring there's something for everyone. Whether you're seeking relaxation or adventure, Siesta Key has a range of activities and trips to make your visit memorable.

Shopping

The Siesta Key Farmers Market offers a charming local vibe and is perfect for fresh produce and unique gifts. For more shopping, Gulf Gate Mall is only 4.8km away, boasting various family-friendly shops and entertainment. If you're up for a drive, Artisans' World Marketplace is 6.4km away, featuring unique artisan goods.

Recreation

Experience the vibrant arts at Van Wezel Performing Arts Hall, just 8.0km from Siesta Key, where culture meets entertainment. For sports enthusiasts, Ed Smith Stadium, 9.7km away, buzzes with energy, while Stoneybrook Golf & Country Club, 11.3km distant, offers a serene outdoor golfing experience.

Adventure

Sarasota BayWalk offers a scenic hiking trail that immerses you in the natural beauty of the area, located 6.4km from Siesta Key. For some energetic fun, visit Payne Park Tennis Center, 8.0km away, where you can engage in thrilling tennis matches amidst adventure vibes.

If you're looking for family-friendly excitement, head to Astro Skate and Fun Center, 20.9km from Siesta Key. This arcade adventure zone promises hours of fun with various games and activities, making it a perfect spot for both kids and adults seeking adventure.

Nightlife

Siesta Key offers a vibrant nightlife with beach bars like the Siesta Key Oyster Bar, perfect for live music and fresh seafood. For a lively atmosphere, visit The Beach Club, where you can dance the night away. Enjoy a laid-back evening at Daiquiri Deck with refreshing cocktails.

Find the best attractions in and around Siesta Key

Siesta Key, Florida, is perfect for beach lovers and families seeking outdoor adventures. With a variety of attractions, including Siesta Key Village, Siesta Key Beach, and local marinas, visitors can enjoy a delightful mix of relaxation and urban experiences. Whether you're lounging on the sand or exploring nearby parks, Siesta Key offers something for everyone looking to unwind in a beautiful setting.

  • Siesta Key Beach: Renowned for its powdery white sands and stunning turquoise waters, Siesta Key Beach offers a quintessential beach experience. Relax under the sun, enjoy beach volleyball, or take a leisurely stroll along the shore while soaking in the vibrant atmosphere.
  • St. Armands Circle: A charming shopping and dining destination located 4.8km from Siesta Key, St. Armands Circle features a mix of upscale boutiques, cafes, and art galleries. Experience the lively city vibes while indulging in gourmet dining and unique shopping.
  • Marie Selby Botanical Gardens: Situated 6.4km from Siesta Key, these gardens provide a romantic and tranquil escape. Wander through lush tropical landscapes, enjoy the stunning orchid collection, and create lasting memories with family amidst the beauty of nature.

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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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.