Siesta Key All inclusive Vacations

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Top All inclusive vacation packages in Siesta Key

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
$619
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
This property is only 3 years old so everything is clean and new. The room was all tile floor with tile showers. Nicely decorated and had updated furniture. I thought the beds were comfortable ( my son and his wife thought they were too firm ) There’s a full size washer and dryer. The kitchen had adequate dishes, pot and pans and utensils. There were TVs is each bedroom and a large wall mounted in the living room. They had Roku which made it easy to use. The pool area had enough lounge chairs and umbrellas. The bar area had nice couches and a long bar to sit at. Mixed drinks were $14 - which is usual for a resort. The only downside was the parking. We needed two spots which they said the they couldn’t accommodate due to being full. We saw a few empty spots each night and morning. The last day, the desk did call me to offer a spot ( for my son) at $25 per night. That night there were a lot of spots available. Also to note, that the resort is located on the beach but the walk to the beach is pretty far and may be difficult for someone with mobility issues. The resort does not supply beach chairs and umbrellas but there is a vendor on the beach that offers rentals ($$$). Overall, we had a great stay. I recommend this resort.

Reviewed on Oct 6, 2026

CW Resort

CW Resort

Save 100% on your flight
$979
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
Incredible place to stay.highly recommended.

Reviewed on Oct 6, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa
Save 100% on your flight
$847
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (943 reviews)
Nice enough place, but the location didn't really support the pricing of this location, plus the bums asking for money etc. Outside the establishments main doors. With that comes with the three guys heckling our beautiful wives, just because we were not with them. Then the walls are thin enough you can hear the lady next door getting railed by her man. Real Classy! Thanks for nothing.

Reviewed on Oct 5, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

Save 100% on your flight
$1,118
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (3,946 reviews)
The Avalon Club

The Avalon Club

Save 100% on your flight
$1,386
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (608 reviews)
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5* All inclusive vacations in Siesta Key

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

The Adaline

Hyde Park
$943
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (75 reviews)
Fantastic property. The area was quiet and it felt very safe and private. Friendly owners and staff.

Reviewed on Sep 21, 2026

The Gemma by Brightwild

The Gemma by Brightwild

Save 100% on your flight
$2,144
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Indian Rocks Escape

Indian Rocks Escape

$2,296
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
No reviews
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3 Night All inclusive vacations in Siesta Key

Price found within the past 48 hours. Click for updated prices.
CW Resort

CW Resort

$597
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
Incredible place to stay.highly recommended.

Reviewed on Oct 6, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
$619
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
This property is only 3 years old so everything is clean and new. The room was all tile floor with tile showers. Nicely decorated and had updated furniture. I thought the beds were comfortable ( my son and his wife thought they were too firm ) There’s a full size washer and dryer. The kitchen had adequate dishes, pot and pans and utensils. There were TVs is each bedroom and a large wall mounted in the living room. They had Roku which made it easy to use. The pool area had enough lounge chairs and umbrellas. The bar area had nice couches and a long bar to sit at. Mixed drinks were $14 - which is usual for a resort. The only downside was the parking. We needed two spots which they said the they couldn’t accommodate due to being full. We saw a few empty spots each night and morning. The last day, the desk did call me to offer a spot ( for my son) at $25 per night. That night there were a lot of spots available. Also to note, that the resort is located on the beach but the walk to the beach is pretty far and may be difficult for someone with mobility issues. The resort does not supply beach chairs and umbrellas but there is a vendor on the beach that offers rentals ($$$). Overall, we had a great stay. I recommend this resort.

Reviewed on Oct 6, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa
Save 100% on your flight
$847
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (943 reviews)
Nice enough place, but the location didn't really support the pricing of this location, plus the bums asking for money etc. Outside the establishments main doors. With that comes with the three guys heckling our beautiful wives, just because we were not with them. Then the walls are thin enough you can hear the lady next door getting railed by her man. Real Classy! Thanks for nothing.

Reviewed on Oct 5, 2026

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4 Night All inclusive vacations in Siesta Key

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
$716
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
This property is only 3 years old so everything is clean and new. The room was all tile floor with tile showers. Nicely decorated and had updated furniture. I thought the beds were comfortable ( my son and his wife thought they were too firm ) There’s a full size washer and dryer. The kitchen had adequate dishes, pot and pans and utensils. There were TVs is each bedroom and a large wall mounted in the living room. They had Roku which made it easy to use. The pool area had enough lounge chairs and umbrellas. The bar area had nice couches and a long bar to sit at. Mixed drinks were $14 - which is usual for a resort. The only downside was the parking. We needed two spots which they said the they couldn’t accommodate due to being full. We saw a few empty spots each night and morning. The last day, the desk did call me to offer a spot ( for my son) at $25 per night. That night there were a lot of spots available. Also to note, that the resort is located on the beach but the walk to the beach is pretty far and may be difficult for someone with mobility issues. The resort does not supply beach chairs and umbrellas but there is a vendor on the beach that offers rentals ($$$). Overall, we had a great stay. I recommend this resort.

Reviewed on Oct 6, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
$947
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (604 reviews)
So clean and anything at all that we needed the staff was more than willing to do great experience

Reviewed on Oct 4, 2026

The Avalon Club

The Avalon Club

Save 100% on your flight
$2,222
per person
Dec 27 - Dec 31
found 10 hours ago
Roundtrip flight included
Minneapolis (MSP) to Tampa (TPA)
9.4/10 Exceptional! (608 reviews)
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All-inclusive Siesta Key vacations: everything you need to know

Can I book a Siesta Key vacation with airfare and meals?

On an all-inclusive vacation, your mind and body can wander far from your wallet. Pay one simple price when you bundle your accommodation and airfare, and you avoid all those yucky bills after conversation-starting cocktails or decadent dinners.

How can I find Siesta Key all-inclusive vacations that are adults only?

All the best all-inclusive, all-adult vacations are a click of a filter or two away. Choose from great grown-up features. Say, a spa for a couple’s massage, a hot tub to soak away the stresses of the day, or a swim-up bar to get the party started.

How much is an all-inclusive trip to Siesta Key?

Affordable all-inclusive is yours, whatever your budget. Packages start tempting you from just $597. Prices and availability are subject to change. Additional terms may apply.

How can I book cheap all-inclusive trips to Siesta Key?

Whenever you book your travel, sorting by price and filtering by budget shows you what’s out there in your price range.

What are the benefits of all-inclusive Siesta Key vacations with airfare?

Create your dream getaway by bundling your flight and hotel and you get delightful deals and discounts. Add your car rental, too, and you save on all three.

What should I think about when I book an all-inclusive Siesta Key family vacation package?

With little tummies taken care of, you just need to put smiles on their faces. Easy! Book an all-inclusive vacation with a full-on water park or epic pools—or book your stay near the world’s biggest theme parks and attractions.

Why should I book an all-inclusive honeymoon package in Siesta Key?

You can start your married life how you mean to go on with an all-inclusive honeymoon package. Eat and drink to your heart’s content, waltz around in happy harmony, and have your fill of delights. Together, you can book up adventure excursions and return to a pool-side cabana for cocktails at sunset.

Can I book an all-inclusive Siesta Key package with free cancellation and/or flexible dates?

When you’re searching for your all-inclusive getaway, filter your results by payment option to find free cancellation and buy now, pay later options. That way, you can rebook without worry, should your plans change.

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

Book amazing all-inclusive adventures, all in one place. Choose from a vast inventory of deals, adding every little extra to build your brilliant break in minutes.

Things to do

Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

$71
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

$59
per adult
94% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
HydroCats - 2 Hour CraigCat Sightseeing Tour

HydroCats - 2 Hour CraigCat Sightseeing Tour

$146
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
See all activities in Siesta Key

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