Siesta Key Vacation Packages

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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.

Top Siesta Key Vacation Deals

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

Mar Bay Motel &Suites

2 out of 5
per person
Aug 26 - Aug 31
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (499 reviews)
Staff was very friendly. Property was clean and well taken care . Right on the beach, volleyball court and a nice bar near pool.

Reviewed on Jul. 2, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.2/10 Wonderful! (1,034 reviews)
The property was quiet, clean and comfortable. The customer service was professional and above average. I would not hesitate to book again. Two bedrooms and two bathrooms, living room and full kitchen was plenty room for husband and I. Only stayed one night but wished it was longer.

Reviewed on Jun. 26, 2025

Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
9.6/10 Exceptional! (544 reviews)
Property was very nice, room was beautifully decorated and very clean and comfortable. Nice kitchenette. The pool and pool area very nice. The location is great. Close to the beach and some restaurants and bars. Each room was provided a wagon, cooler, chairs and umbrella to use for the beach which was so nice. I would definitely stay there again!

Reviewed on Jun. 29, 2025

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.2/10 Very Good! (1,001 reviews)
We asked for late check-out twice, and received no response.

Reviewed on Jun. 30, 2025

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(12 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

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 (2 kilometres 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 16,764 cm 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.

Ready to book your vacation to Siesta Key?

 

Choose your dates

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 CA $241 per night from Jul 9 to Jul 10
CA $241
CA $303 total
Jul 9 - Jul 10
includes taxes & fees
9.2/10 Wonderful! (4,738 reviews)
"Staff was so friendly and helpful. There were plenty of transportation options as well as walkable sites for entertainment and food. Beach and pool very close by."

Reviewed on Jul. 2, 2025

Tropical Beach Resorts
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 CA $332 per night from Jul 24 to Jul 25
CA $332
CA $420 total
Jul 24 - Jul 25
includes taxes & fees
8.8/10 Excellent! (1,023 reviews)
"Best hotel"

Reviewed on Jul. 1, 2025

Tropical Breeze Resort
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 CA $255 per night from Jul 14 to Jul 15
CA $255
CA $364 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (1,025 reviews)
"Great stay, I have one issue. They need to put up curtains, they have new shades the light comes straight through. Hard sleeping as the light was on all night. Need black out curtains. Stayed in room 115."

Reviewed on Jun. 29, 2025

Siesta Key Beach Resort and Suites
See all 3,821 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Siesta Key vacation package cost?
You'll find cheap prices from CA $798 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.

Discover the most popular places to visit in Siesta Key

Siesta Key Beach

Siesta Key Beach

4.5/5(75 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

5/5(5 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

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

What to do in Siesta Key

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

CA $76
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Private Luxury Boat Charter

Private Luxury Boat Charter

CA $515
per traveller
100% of travellers recommend
Private Luxury Boat Charter
4 Hour Inshore Fishing Charter Sarasota Siesta Key Bradenton

#1 Top Rated - Calm Water Inshore Fishing Charter In Your Area

CA $822
per traveller
#1 Top Rated - Calm Water Inshore Fishing Charter In Your Area
See all activities in Siesta Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.