Siesta Key Vacations from $451

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Your Siesta Key Vacation

Its laid-back lifestyle, laid-back lifestyle and beaches are just the start of the reasons to book a vacation package to Siesta Key. No matter your reason for coming to this Gulf of Mexico city, you're sure to have a fantastic experience. If taking in sights is part of the program during your trip to Siesta Key, visit top attractions like Siesta Key Beach, St. Armands Circle and Mote Marine Laboratory & Aquarium. Don't delay your visit to this destination any longer. Your perfect Siesta Key vacation is only a few clicks away with Expedia.

The Latest Siesta Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $792, price is now $451 per person
$451
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Excellent customer service

Reviewed on Dec 14, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Price was $3,501, price is now $1,911 per person
$1,911
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (294 reviews)
The property has everything you need and right on the beach. The 2 bedroom villa was exceptionally clean and large with nice balcony. The service and staff were great. We will definitely come back again!

Reviewed on Jan 4, 2026

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was $933, price is now $519 per person
$519
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended

Reviewed on Jan 1, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was $2,845, price is now $1,629 per person
$1,629
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Staff was very accommodating and the Jr. Suite pleasant to come back to after my little adventures.

Reviewed on Jan 10, 2026

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,930, price is now $1,113 per person
$1,113
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
7/10 Good! (1,744 reviews)
Staff was wonderful! Food was good and everything else met my expectations 😊

Reviewed on Jan 9, 2026

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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
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South Village

1 out of top 10 points of interest in this area

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

Find hotels in South Village

Discover the most popular places to visit in Siesta Key

Southwest Florida featuring general coastal views and a beach as well as a large group of people

Siesta Key Beach

4.5/5(1,425 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.

Siesta Key Beach
Crescent Beach

Crescent Beach

4.5/5(146 reviews)

Why not spend a carefree afternoon at Crescent Beach during your travels in Siesta Key? Stroll along the seaside or discover the sunsets in this relaxing area.

Crescent Beach

Point of Rocks

4.5/5(31 reviews)

Enjoy the beautiful sunsets and explore Point of Rocks, a lovely green space in Siesta Key. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Point of Rocks

What to do in Siesta Key

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$59
per adult
92% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

$65
per adult
74% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

$65
per adult
84% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
See all activities in Siesta Key

Siesta Key Hotel Deals

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $185 total per night from Jan 12 to Jan 13
$185 total
Jan 12 - Jan 13
Total with taxes and fees
9.2/10 Wonderful! (5,196 reviews)
This is the third time I've stated Tropical Beach Resorts, and it has been amazing every time. The rooms are great, the grounds are so lovely and well maintained, the new pool is fantastic, and the beach is gorgeous. Can't wait to go back again someday!

Reviewed on Jan 4, 2026

Tropical Beach Resorts
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
6772 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $270 total per night from Jan 12 to Jan 13
$270 total
Jan 12 - Jan 13
Total with taxes and fees
9/10 Wonderful! (1,185 reviews)
This hotel was great! We had a two bedroom suite for a very reasonable rate. Well stocked kitchen, clean, close to the beach, easy parking, nice front desk staff. I would recommend this hotel very much.

Reviewed on Jan 2, 2026

Captiva Beach Resort
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd Siesta Key FL
$237 nightly
The price is $268 total per night from Jan 12 to Jan 13
$268 total
Jan 12 - Jan 13
Total with taxes and fees
8.8/10 Excellent! (1,044 reviews)
Everything was great except the Mattress was terrible needs to be replaced..........

Reviewed on Jan 6, 2026

Siesta Key Beach Resort and Suites
See all 3,912 properties in Siesta Key
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.

Find the Best Siesta Key Vacation Packages

Things to do in and around Siesta Key

Siesta Key is perfect for family vacations, offering stunning beaches and outdoor activities. Popular attractions include recreational areas, resorts, and shopping centers. For an unforgettable experience, consider exploring the best vacation packages, joining a kayak tour, or playing on the tennis courts. Don’t miss the sightseeing opportunities and the chance to discover hidden beaches that make Siesta Key a unique destination.

Shopping

The Siesta Key Farmers Market offers a charming local vibe, perfect for unique gifts. For a larger shopping experience, Gulf Gate Mall is just 3 miles away, featuring various stores and entertainment options. Bay Isles Shopping Center, located 4 miles from Siesta Key, also provides a variety of shopping choices.

Recreation

Experience the vibrant culture at Van Wezel Performing Arts Hall with captivating shows just 5 miles from Siesta Key. Enjoy a day of sports at Ed Smith Stadium, 6 miles away, or embrace the outdoors at Gulf Gate Golf Club, located 4 miles from the beach.

Adventure

Explore the scenic Sarasota BayWalk, a hiking trail 4 miles from Siesta Key, or enjoy family fun at Astro Skate and Fun Center, located 13 miles away. For tennis enthusiasts, Payne Park Tennis Center offers adventurous activities 5 miles from Siesta Key, perfect for a day of outdoor excitement.

Nightlife

Siesta Key's nightlife features vibrant beach bars and live music venues. Check out the Siesta Key Oyster Bar for great seafood and local bands. For a laid-back vibe, visit The Beach Club, where you can dance the night away with ocean views and refreshing cocktails.

*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 is perfect for family vacations, offering beautiful beaches and outdoor activities. Explore popular attractions like Siesta Key Beach, Siesta Key Palms, and local urban parks. Whether you’re interested in relaxing by the water or enjoying a vibrant city experience, there are plenty of options to ensure a memorable visit. Don't miss out on the marina for additional recreational opportunities.

  • Siesta Key Beach: Famous for its powdery white sands and crystal-clear waters, Siesta Key Beach offers a laid-back atmosphere perfect for sunbathing, swimming, and beach volleyball. The vibrant sunset views make it a must-visit for beach lovers.
  • St. Armands Circle: A charming shopping and dining district located 3 miles from Siesta Key, St. Armands Circle boasts a unique blend of upscale boutiques, art galleries, and diverse eateries. Enjoy the lively city vibes while exploring this picturesque area.
  • Marina Jack: Just 4 miles away, Marina Jack is a waterfront paradise offering boating, dining, and outdoor activities. Experience adventure on the water or relax at the marina while enjoying stunning views of Sarasota Bay.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately HighAverage
February65.1°F (18.4°C)No RainMostly SunnyAverageSlightly High
March68.0°F (20.0°C)No RainSunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately HighAverage
August83.3°F (28.5°C)Light RainMostly SunnyAverageSlightly Low
September81.5°F (27.5°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowAverage
November70.7°F (21.5°C)No RainMostly SunnyModerately LowSlightly Low
December66.6°F (19.2°C)No RainMostly SunnyModerately LowAverage

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.

Siesta Key Beach Vacation

Unwind on the shore while you gaze at the sunlight sparkling on the water during your Siesta Key vacation. If you're yearning for a complete beach experience, a trip to Siesta Key certainly delivers. There's a good chance you've heard of Siesta Key Beach (1 mile away). We suggest finding accommodations close by. However, plenty of visitors also opt for Siesta Key vacation packages that are closer to Crescent Beach or Shell Beach, two other superb nearby options.

Things You Should Know About Siesta Key

  • Spend your getaway by the water and let the stresses and strains of daily life drift away with the sea breeze. Check out our Siesta Key beach hotels and discover beachside bliss.
  • Our condos, like Hyatt Siesta Key Beach and Siesta Key Inn, are popular with visitors of all sorts. Consider the amenities and get ready for your stay in Siesta Key!
  • Be sure to visit our Siesta Key things to do page for some trip planning inspiration. With a population of 6,600 in Siesta Key, we're sure there'll be one or two locals who'll be happy to give you some extra advice!
  • Turtle Beach, Crescent Beach and Crescent Beach are just some of the attractions that should be on your travel schedule. With our Siesta Key vacation deals, you'll have more money in your pocket to explore.

Siesta Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sarasota-Bradenton Intl. Airport (SRQ)
Population
6,600
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Siesta Key Beach, Lido Beach and Turtle Beach

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Frequently asked questions

How much does a Siesta Key vacation package cost?
Offering great value package deals from $451 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?

  1. Choose your dates: The things you'd like to do in Siesta Key and your preferred season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

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