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.

Saddlebrook Resort

Wesley Chapel South

$589

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

8/10 Very Good! (172 reviews)

The self parking lot and shuttles did not run frequently. The rooms were nice and clean.

Reviewed on Oct 20, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$2,313

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

CW Resort

$909

per person

Jan 14 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Beautiful place to stay

Reviewed on Oct 23, 2026

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

Save 100% on your flight

$1,025

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

8.6/10 Excellent! (943 reviews)

Nice place

Reviewed on Oct 18, 2026

Landing St. Petersburg Near South Branch Potomac River

Save 100% on your flight

$1,677

per person

Dec 23 - Dec 30

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

5* All inclusive vacations in Siesta Key

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

The Adaline

Hyde Park

$982

per person

Jan 7 - Jan 12

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

9.6/10 Exceptional! (75 reviews)

Clean and a great location. Very noisy as you can hear the guest conversations in the units next to you. Tons of Amazon packages at the front door can make it hard to access. Hangers in the closet would be nice. Bathroom was clean but so small the tp kept getting wet when you showered.

Reviewed on Oct 18, 2026

The Gemma by Brightwild

$2,303

per person

Dec 17 - Dec 20

found 15 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

$8,495

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9.8/10 Exceptional! (97 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

3 Night All inclusive vacations in Siesta Key

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

CW Resort

$547

per person

Dec 17 - Dec 20

found 15 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Beautiful place to stay

Reviewed on Oct 23, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

$969

per person

Jan 1 - Jan 4

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

$667

per person

Jan 7 - Jan 10

found 15 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

8.6/10 Excellent! (943 reviews)

Nice place

Reviewed on Oct 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

4 Night All inclusive vacations in Siesta Key

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

Landing Palmetto Apartments

$696

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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

CW Resort

$909

per person

Jan 14 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Beautiful place to stay

Reviewed on Oct 23, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,905

per person

Dec 29 - Jan 2

found 12 hours ago

Roundtrip flight included

Islip (ISP) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Siesta Key

View all trips

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 $547. 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.