Siesta Key Vacations

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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
Siesta Key Village

Siesta Key Village

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

Travelers to Siesta Key Village praise its stunning beaches. If you've got some more time to explore, be sure to make a stop by Siesta Key Beach and Siesta Key Farmers Market.

Find hotels in Siesta Key Village

Find the Best Siesta Key Vacation Packages

Siesta Key Hotel Deals

Tropical Beach Resorts
Tropical Beach Resorts
3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
The price is SAR 1,103 per night from Mar 10 to Mar 11
SAR 1,103
SAR 1,332 total
includes taxes & fees
10 Mar - 11 Mar
9.2/10 Wonderful! (4,567 reviews)
"A little solo trip down to Siesta key with no plans. Stumbled on this beautiful place and couldn’t be more please. In a place where everything is so expensive this was a reasonable gem. Highly recommend this place 10 out of 10."

Reviewed on 7 March 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 SAR 1,779 per night from Mar 10 to Mar 11
SAR 1,779
SAR 2,218 total
includes taxes & fees
10 Mar - 11 Mar
8.6/10 Excellent! (1,009 reviews)
"Very clean great staff everyone was so helpful and happy! Cozy room! Only thing that we had a hard time with was the lights outside stay on all night and illuminate the room even with the wood blinds closed! I did speak to someone at the office and they said the lights were new and that they appreciated ..."

Reviewed on 5 March 2025

Siesta Key Beach Resort and Suites
Siesta Key Beachside Villas
Siesta Key Beachside Villas
2.5 out of 5
124 Columbus Blvd, Siesta Key, FL
The price is SAR 1,564 per night from Mar 13 to Mar 14
SAR 1,564
SAR 1,974 total
includes taxes & fees
13 Mar - 14 Mar
8.8/10 Excellent! (778 reviews)
"A gem in Siesta Key - very laid back vibe."

Reviewed on 4 March 2025

Siesta Key Beachside Villas
See all 3,832 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.

Frequently asked questions

How much does a Siesta Key vacation package cost?
Offering great value package deals 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?
September, October and November are the best times to look for cheap Siesta Key vacation packages. Traveling in less busy periods means you can typically find reduced prices on accommodations and flights.
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 when to get away: Check your calendar and get your bags packed. Your favorite 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 accommodations 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 customized Siesta Key vacation package.

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)

Nothing says vacation like spending a lazy day at Siesta Key Beach, a popular beach in Siesta Key. Amble around this relaxing area's seaside or experience its live music.

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