Search Deals on
Siesta Key Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

A coastal city with a long sandy beach, a marina, and several high-rise buildings.

Siesta Key
Florida
United States of America
North America
Hotwire.com

Siesta Key Flight + Hotel Packages

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

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5

Save 100% on your flight

Price was $765, price is now $485 per person

$485

per person

Dec 23 - Dec 27

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Ocean Club Treasure Island Hotel

4 out of 5

Save 100% on your flight

Price was $1,491, price is now $894 per person

$894

per person

Dec 27 - Dec 30

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Very clean place, great staff but had bathroom issues which they will fix! But overall good.

Reviewed on Oct 16, 2026

Anna Maria Beach Resort

3.5 out of 5

Save 100% on your flight

Price was $2,872, price is now $1,870 per person

$1,870

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Book a stay at this beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.

We loved the Anna Maria Beach Resort and plan on returning for another vacation!

Reviewed on Oct 15, 2026

Siesta Key Inn

2 out of 5

Save 100% on your flight

Price was $1,571, price is now $1,031 per person

$1,031

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Great place to stay close to the beach. The apartment is fully equipped, very clean, new appliances. Excellent communication! I definitely recommend this place, you won’t be disappointed.

Reviewed on Oct 16, 2026

Siesta Palms By the Beach

3.5 out of 5

Save 100% on your flight

Price was $1,566, price is now $1,039 per person

$1,039

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

voco Sarasota by IHG

3.5 out of 5

Save 100% on your flight

Price was $824, price is now $553 per person

$553

per person

Dec 23 - Dec 27

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.

Cedar Cove Resort and Cottages

3 out of 5

Save 100% on your flight

Price was $2,401, price is now $1,641 per person

$1,641

per person

Jan 3 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.

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

Reviewed on Oct 13, 2026

Stylish Treasure Island Escape

3 out of 5

Save 100% on your flight

Price was $5,305, price is now $3,629 per person

$3,629

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Tampa (TPA)

Stay at this apartment in Treasure Island. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.