Siesta Key Holidays

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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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Siesta Key Village

1 out of top 10 points of interest in this area
5/5(1 area review)

Siesta Key Village is known for its stunning beaches, and with sights like Siesta Key Beach and Siesta Key Farmers Market, you won't get bored spending a day wandering around this part of Siesta Key.

Find hotels in Siesta Key Village

Top hotels in Siesta Key

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 5.086.399 ₫ per night from 24 Jun to 25 Jun
5.086.399 ₫
6.338.335 ₫ total
24 Jun - 25 Jun
includes taxes & fees
9.2/10 Wonderful! (4,712 reviews)
"Pleasant check-in experience. Well maintained property. Room was small but perfect for our stay. Clean with nice amenities. Convenient location on trolley route. Wish we could've stayed longer but we'll be back!"

Reviewed on 20 Jun 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 9.148.463 ₫ per night from 27 Jun to 28 Jun
9.148.463 ₫
11.784.819 ₫ total
27 Jun - 28 Jun
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
"What a great stay on Siesta key. Right down the street from stores and restaurants. Resort is so convenient to the beach and has great amenities like beach chairs, cooler and access to beach wagon. The only thing they don’t have is a beach umbrella so bring one or be prepared to purchase one at one ..."

Reviewed on 19 Jun 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 7.677.810 ₫ per night from 7 Jul to 8 Jul
7.677.810 ₫
9.717.036 ₫ total
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"We had a wonderful time last week and a Luxury 1 bedroom suite to die for . Staff was amazing and would definitely stay again. Beach chairs great and your literally a few block walk to the beach . Beach just absolutely beautiful and sunset 🌅 was a must . All restaurants and shops walking distance. ..."

Reviewed on 19 Jun 2025

Tropical Breeze Resort
See all 3,813 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 holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday 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 holiday packages. Travelling in less busy periods means you can typically find reduced prices on accommodation and flights.
How many days is enough for Siesta Key?
Dedicate around 4 days for your Siesta Key holiday to really take in all that makes this destination unique. Stroll around key neighbourhoods, including Central Sarasota and Siesta Key Village. Then head to the major sights like Shell Beach and Irma Beach. With a good itinerary, you can keep busy with room for some rest time too. Want to venture beyond Siesta Key? Consider an excursion or two.
Is it worth booking a holiday package to Siesta Key?
Boasting a host of highlights starting with its amazing coastal beaches, Siesta Key is a good holiday destination. Whether you'd like to discover attractions like Bay Island and Siesta Key Beach or take the road less traveled, you'll have plenty to see and do on your Siesta Key holiday.
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 holiday as a package?
You can enjoy significant savings on your next Siesta Key escape by booking a tailored holiday 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 holiday 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 favourite 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 accommodation 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 customised Siesta Key holiday package.

Popular places to visit

Siesta Key Beach

Siesta Key Beach

4.5/5(33 reviews)

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

Siesta Key Beach
Crescent Beach

Crescent Beach

4.5/5(3 reviews)

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

Crescent Beach

Jim Neville Marine Preserve

Explore the great outdoors at Jim Neville Marine Preserve and enjoy the beautiful sunsets during your trip to Siesta Key. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Jim Neville Marine Preserve