Siesta Key All inclusive Vacations 2026

Top All inclusive vacation packages in Siesta Key

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

Ocean Club Treasure Island Hotel

Sunshine Beach

$737

per person

Nov 20 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The property was amazing. Very well maintained and the staff was great. Everyone was very friendly and helpful. We have no complaints and will be staying again soon.

Reviewed on Oct 12, 2026

Landing St. Petersburg Near South Branch Potomac River

Save 100% on your flight

$798

per person

Dec 4 - Dec 11

found 17 hours ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

No reviews

Legacy Hotel at IMG Academy

$925

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

The Avalon Club

$1,223

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

Landing Palmetto Apartments

$1,124

per person

Dec 30 - Jan 4

found 7 hours ago

Roundtrip non-stop flight included

New York (JFK) to Sarasota (SRQ)

9/10 Wonderful! (71 reviews)

The apartment had everything we needed. The bathroom vanity was a pedestal sink with no counter space for toiletries.

Reviewed on Oct 12, 2026

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5* All inclusive vacations in Siesta Key

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

Indian Rocks Escape

$1,390

per person

Dec 17 - Dec 20

found 9 hours ago

Roundtrip flight included

New York (NYC) to Tampa (TPA)

No reviews

The Gemma by Brightwild

Save 100% on your flight

$2,225

per person

Nov 28 - Dec 1

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

The St. Regis Longboat Key Resort

$8,247

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (97 reviews)

Beach view and staff

Reviewed on Oct 9, 2026

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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

Save 100% on your flight

$1,041

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Nice hotel.

Reviewed on Oct 12, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

$1,432

per person

Dec 26 - Dec 29

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The property was amazing. Very well maintained and the staff was great. Everyone was very friendly and helpful. We have no complaints and will be staying again soon.

Reviewed on Oct 12, 2026

The Avalon Club

$1,223

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

Reviewed on Oct 7, 2026

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4 Night All inclusive vacations in Siesta Key

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

Hibiscus Suites - Gateway to Siesta Key

$752

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (2,455 reviews)

Clean rooms and staff was perfect very friendly

Reviewed on Oct 11, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$944

per person

Nov 13 - Nov 17

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

Property was great. Loved the location. On the quieter side but close to everything

Reviewed on Oct 13, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$791

per person

Nov 18 - Nov 22

found 12 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The property was amazing. Very well maintained and the staff was great. Everyone was very friendly and helpful. We have no complaints and will be staying again soon.

Reviewed on Oct 12, 2026

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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 $737. 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.