Siesta Key All inclusive Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Flight and All inclusive hotel deals in Siesta Key

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

CA $1,075
per person
Dec 26 - Dec 30
found 14 hours ago
Roundtrip flight included
Buffalo (BUF) to Tampa (TPA)
9.4/10 Exceptional! (3,946 reviews)
Very clean and good service

Reviewed on Oct 14, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
CA $2,139
per person
Dec 26 - Dec 30
found 14 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
This property was amazing! On the beach and the rooms excellent!! Would absolutely stay here again!

Reviewed on Oct 15, 2026

CW Resort

CW Resort

Save 100% on your flight
CA $1,138
per person
Dec 16 - Dec 21
found 12 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
The Avalon Club

The Avalon Club

Save 100% on your flight
CA $2,285
per person
Dec 27 - Dec 31
just found
Roundtrip flight included
Hamilton (YHM) to Tampa (TPA)
9.4/10 Exceptional! (608 reviews)
Great place to stay with the family. Rooms were clean and spacious. Parking was easy. Walkable to many stores and restaurants. Very close to the beach, and the hotel has everything needed for your beach day: towels, chairs, umbrellas, floaties, and sand toys.

Reviewed on Oct 7, 2026

The Westin Sarasota

The Westin Sarasota

Central Sarasota
Save 100% on your flight
CA $2,088
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
9.2/10 Wonderful! (1,178 reviews)
All good thanks for a lovely stay

Reviewed on Oct 14, 2026

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5* All inclusive holidays in Siesta Key

Price found within the past 48 hours. Click for updated prices.
Indian Rocks Escape

Indian Rocks Escape

CA $1,479
per person
Dec 11 - Dec 13
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
No reviews
The Gemma by Brightwild

The Gemma by Brightwild

CA $3,113
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.8/10 Exceptional! (7 reviews)
The Jade House is in an excellent location only a block from the beach and short walk to restaurants, shops, and bars. Communication with the management company was difficult through Expedia. Even when I called directly, one of the three client service agents was not helpful whatsoever. However, once I was given the number to text, communication was much better. The pool/ hot tub area is perfect. The house is very comfortable. Only decks are narrow (only stand); ocean view is from one of theses.

Reviewed on Jul 30, 2026

The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

CA $11,625
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.8/10 Exceptional! (97 reviews)
Don't see what you're looking for?
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3 Night All inclusive holidays in Siesta Key

Price found within the past 48 hours. Click for updated prices.
The Avalon Club

The Avalon Club

Save 100% on your flight
CA $1,249
per person
Nov 23 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (608 reviews)
Great place to stay with the family. Rooms were clean and spacious. Parking was easy. Walkable to many stores and restaurants. Very close to the beach, and the hotel has everything needed for your beach day: towels, chairs, umbrellas, floaties, and sand toys.

Reviewed on Oct 7, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
CA $1,609
per person
Dec 27 - Dec 30
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
This property was amazing! On the beach and the rooms excellent!! Would absolutely stay here again!

Reviewed on Oct 15, 2026

CW Resort

CW Resort

Save 100% on your flight
CA $1,876
per person
Dec 31 - Jan 3
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
Don't see what you're looking for?
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4 Night All inclusive holidays in Siesta Key

Price found within the past 48 hours. Click for updated prices.
Siesta Palms By the Beach

Siesta Palms By the Beach

South Village
Save 100% on your flight
CA $1,603
per person
Nov 19 - Nov 23
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (178 reviews)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
CA $2,139
per person
Dec 26 - Dec 30
found 14 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
This property was amazing! On the beach and the rooms excellent!! Would absolutely stay here again!

Reviewed on Oct 15, 2026

CW Resort

CW Resort

Save 100% on your flight
CA $1,970
per person
Dec 27 - Dec 31
just found
Roundtrip flight included
Hamilton (YHM) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
Don't see what you're looking for?
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Embark on an unforgettable all-inclusive trip to Siesta Key including airfare with Expedia

What are some benefits of booking an all-inclusive vacation?

When you opt for an all-inclusive vacation to Siesta Key, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget.

Can I book all-inclusive packages with airfare and meals?

Yes, all-inclusive vacation packages are readily available for Siesta Key, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 24.

Why should I book Siesta Key vacations that are all inclusive and adults only?

Adults-only stays in Siesta Key are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find.

Can I book all-inclusive packages?

Yes, all-inclusive packages are fairly standard in Siesta Key. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive.

Can I book cheap all-inclusive trips to Siesta Key?

If you're looking to save, you'll find a wide range of prices available, ranging from CA $1,075. By booking your accommodations and flight together, you may be able to enjoy savings of up to 24. Be sure to sort your search results by price to list the cheapest options first.

What should I look for when booking a 5-star all-inclusive vacation in Siesta Key?

If you've implemented the 5-star filter when searching for your all-inclusive vacation in Siesta Key, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group.

What should I consider when booking Siesta Key vacation packages that are all inclusive for the family?

The most important thing to consider for all-inclusive family vacations to Siesta Key is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying Siesta Key's nightlife.

How can I find the best deals on all-inclusive vacations in Siesta Key?

You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters.

Can I book an all-inclusive package that is fully refundable?

Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify.

Why should I book an all-inclusive vacation with Expedia?

Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts.

Things to do

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

CA $91
per adult
86% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

CA $100
per adult
96% of travellers recommend
Siesta Key Electric Bike Sunset Tour
Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

CA $83
per adult
96% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
See all activities in Siesta Key

More vacations you might like

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