Siesta Key Vacations from $292

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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.
Weathered The Storm

Weathered The Storm

3 out of 5
per person
Jul 7 - Jul 11
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
2/10 (3 reviews)
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (3,649 reviews)
How easy and quick the whole process was.

Reviewed on Apr 28, 2025

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
North Trail
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (1,794 reviews)
Nice renovation on an iconic old Florida motel with lively tiki bar. Excellent front desk service.

Reviewed on Apr 27, 2025

Carlisle Inn

Carlisle Inn

3.5 out of 5
Pinecraft
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
10/10 Exceptional! (1,754 reviews)
The Carlisle is definitely a 10/10! It is a lovely surprise for my first visit to Sarasota. It is super clean and very well managed. People there are friendly and helpful. The room is spacious, simple and comfortable. The breakfast even have self-made waffles, my wife loves it. The hotel location is great, very easy to access to major places. We took a walk on the legacy trail (which literally pass the backyard of the hotel)in the early morning, turns out to be a highlight of our visit this time. We are going to Sarasota again in early June, will definitely stay there again.

Reviewed on Apr 27, 2025

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
Save 100% on your flight
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (1,081 reviews)

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
Siesta Key Village

Siesta Key Village

1 out of top 10 points of interest in this area
4.5/5(282 area reviews)

Tropical colored buildings, lots of sandy beaches and a compact shopping area make this village a good choice to visit and stay. Enjoy an on-going social life too.

Find hotels in Siesta Key Village

Find the Best Siesta Key Vacation Packages

Siesta Key Beach Vacation

It's time to slow things right down and enjoy a cocktail by the sea on a Siesta Key vacation. Beautiful coastal vistas are bountiful on a trip to Siesta Key — Siesta Key Public Beach (1 mile (1 km) away) is an excellent example. You'll love being able to walk there from your hotel. If you're looking for other options, many travelers also take advantage of Siesta Key vacation packages in the vicinity of Turtle Beach and Siesta Key Beach.

Things You Should Know About Siesta Key

  • Listening to the soothing sounds of lapping waves is one of life's small pleasures. See what you can find among our Siesta Key beach hotels and get ready to relax.
  • Condos are also popular with visitors to this area. Gulf Holiday by Beachside Management and Siesta Beach House #210 Beautiful Updated Unit 2 Bedroom Condo are good examples of what you can expect from this accommodation style.
  • Alternatively, let one of our All-Inclusive hotels in Siesta Key take care of all the finer details. That means more time for you to focus on the pressing task of relaxing.
  • Want to know what Siesta Key has to offer? It's hard to go past local knowledge. After you arrive, chat to one or two of the 6,600 people who call this place home. Check out our handy Siesta Key things to do page, too.
  • Save big bucks on unforgettable experiences with our Siesta Key vacation deals. Visit Siesta Key Public Beach, as well as other top attractions, with the extra dollars in your wallet.

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

Ready to book your vacation to Siesta Key?

 

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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
The price is $214 per night from May 19 to May 20
$214
includes taxes & fees
$189 per night
May 19 - May 20
9.2/10 Wonderful! (4,636 reviews)
"Stayed in the new section of rooms, very clean, no issues. will stay here again."

Reviewed on Apr 25, 2025

Tropical Beach Resorts
Siesta Key Beach Resort and Suites
Siesta Key Beach Resort and Suites
2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
The price is $337 per night from May 19 to May 20
$337
includes taxes & fees
$298 per night
May 19 - May 20
8.6/10 Excellent! (1,005 reviews)
"For me the most important thing was the cleanliness, I loved it, I will return"

Reviewed on Apr 26, 2025

Siesta Key Beach Resort and Suites
Tropical Breeze Resort
Tropical Breeze Resort
3 out of 5
140 Columbus Blvd., Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is $372 per night from Apr 29 to Apr 30
$372
includes taxes & fees
$329 per night
Apr 29 - Apr 30
8.8/10 Excellent! (1,003 reviews)
"Loved it. Would return."

Reviewed on Apr 25, 2025

Tropical Breeze Resort
See all 3,800 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Siesta Key vacation package cost?
Offering great value package deals from $292 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.

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

$55
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Private Luxury Boat Charter

Private Luxury Boat Charter

$375
per traveler
100% of travellers recommend
Private Luxury Boat Charter
Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

$71
per adult
98% of travellers recommend
Siesta Key Electric Bike Sunset Tour
See all activities in Siesta Key

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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.