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.

Barsala At The Wayland Condos

4 out of 5
Save 100% on your flight
per person
Jul. 1 - Jul. 8
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
No reviews
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Jul. 1 - Jul. 8
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (386 reviews)
Very nice place and facilities! Staff was very friendly and accommodating to our needs with our luggage and etc. Beds were very comfortable and place was very clean! We had a great time!

Reviewed on Apr. 28, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jun. 12 - Jun. 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (393 reviews)
My family enjoyed our time at the Avalon Club.

Reviewed on Apr. 21, 2025

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jul. 1 - Jul. 8
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9/10 Wonderful! (418 reviews)
Great cottages on the beach. Amenities galore. Just bring yourself and cloths.

Reviewed on Apr. 28, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Jul. 1 - Jul. 8
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,015 reviews)
We love this place. Best part is in the morning watching dolphins from the balcony.

Reviewed on Mar. 29, 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

Gold Coast Beach Vacation

Take a break from the stresses of everyday life and relax on your Gold Coast vacation. There's nothing more invigorating than the smell of salty sea air and the sound of waves crashing onto the shore. Organize your trip to Gold Coast the quick and easy way by locking in one of our Gold Coast packages. Many travelers decide to spend their nights close to Golden Beach, a must-see just 0.2 miles (0.3 km) from the city center.

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
The price is CA $219 per night from May 11 to May 12
CA $219
CA $279 total
includes taxes & fees
May 11 - May 12
"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 CA $395 per night from May 11 to May 12
CA $395
CA $522 total
includes taxes & fees
May 11 - May 12
8.6/10 Excellent! (1,000 reviews)
"Highly recommend"

Reviewed on Apr. 28, 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 CA $406 per night from May 11 to May 12
CA $406
CA $514 total
includes taxes & fees
May 11 - May 12
8.8/10 Excellent! (1,004 reviews)
"Steps to shopping area and just a 5 min walk to the beach…."

Reviewed on Apr. 26, 2025

Tropical Breeze Resort
See all 3,808 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 $1,531 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 $519
per traveller
100% of travellers recommend
Private Luxury Boat Charter
Siesta Key Guided Eco Tour

Siesta Key Guided Eco Tour

CA $82
per adult
100% of travellers recommend
Siesta Key Guided Eco Tour
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.