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.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 31
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,040 reviews)
Wonderful reception

Reviewed on Jul. 14, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 31
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (518 reviews)
We totally shocked how elegant the room was. It was large and well stocked. The beach was a longer walk than normal but beautiful view. Best place we have stayed in a while. We loved it and will be back!

Reviewed on Jul. 16, 2025

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 31
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Sarasota (SRQ)
9.2/10 Wonderful! (445 reviews)
My family and I had a wondeful stay here, beds were comfortable, ac worked well, friendly and attentive staff, etc. Definitely recommend staying here and will be back soon.

Reviewed on Jun. 20, 2025

The Pointe Condos by Barsala

The Pointe Condos by Barsala

4.5 out of 5
Port Tampa City
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9/10 Wonderful! (151 reviews)
The insulation was awful. We could hear everything going on above us. It sounded like they were stomping and moving furniture. When the air conditioner kicked on you had to turn the tv up quite a bit to hear it

Reviewed on Jun. 10, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.8/10 Exceptional! (269 reviews)
Everything was wonderful from start to finish!! We love the location on Siesta key beach! We stayed in a spacious 3 bedroom, 3 bath villa with a nice terrace. The villas are absolutely beautiful with everything you can imagine. Top of the line everything in the kitchen and baths. Nespresso machine, blender... added to the enjoyment. Shampoo, cond & body wash in each shower, and small tubes of lotions available; basic kitchen supplies and laundry detergent. The property is small with only about 44 units, which we enjoyed and it didn't seem crowded. Easy beach access with plenty of chairs and umbrellas for your use at no charge. A lot of pool side loungers and cabanas also free of charge and first come basis. Also available a small fitness club, 2nd floor terrace with pool and ping pong tables, an owners lounge and breakfast spot. Breakfast every day is included and had pastries, oatmeal, cereal, yogurt, fruits, and hard boiled eggs, coffee, tea, milk & juice. These are high end timeshare ownership type villas and it was definitely a step above your typical villa. Service was wonderful and helpful. We were able to use the property after check out as we had a late flight and there are showers in the fitness center with towels etc. There is a small bar poolside; drinks are expensive, but potent!! :) They do offer a small menu, but we did not order any food. Short walk to restaurants, convenience store, sandwich shop, ice cream.Highly recommend!

Reviewed on Jul. 5, 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
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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?

 

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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 CA $197 per night from Aug 3 to Aug 4
CA $197
CA $253 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (4,766 reviews)
"Great location. Close to private beach and walking distance to awesome restaurants and nightlife. Very friendly staff."

Reviewed on Jul. 13, 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 $221 per night from Aug 10 to Aug 11
CA $221
CA $325 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,019 reviews)
Location location location!!
"My son and I stayed in a pool side room. Air conditioning was key. We walked everywhere and the free bikes were awesome. Siesta Key Village is right out your door. Food is good at the restaurant. Music is loud so I would avoid "bar" side rooms. Hotel manager is awesome. Short stroll to the beach ..."

Reviewed on Jul. 14, 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 $275 per night from Aug 14 to Aug 15
CA $275
CA $348 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Whole stay was great"

Reviewed on Jul. 13, 2025

Tropical Breeze Resort
See all 3,862 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

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 $75
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Private Luxury Boat Charter

Private Luxury Boat Charter

CA $513
per traveller
100% of travellers recommend
Private Luxury Boat Charter
Siesta Key Guided Eco Tour

Siesta Key Guided Eco Tour

CA $81
per adult
100% of travellers recommend
Siesta Key Guided Eco Tour
See all activities in Siesta Key

Frequently asked questions

How much does a Siesta Key vacation package cost?
You'll find cheap prices from CA $1,091 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.