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Siesta Key Vacation Packages

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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 1 day 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 1 day 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.

Cedar Cove Resort and Cottages

3 out of 5

Save 100% on your flight

Price was $1,995, price is now $1,217 per person

$1,217

per person

Nov 29 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

CW Resort

4 out of 5

Save 100% on your flight

Price was $908, price is now $566 per person

$566

per person

Nov 25 - Nov 28

found 8 hours ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

Siesta Key Inn

2 out of 5

Save 100% on your flight

Price was $1,415, price is now $917 per person

$917

per person

Nov 24 - Nov 27

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

La Tortuga Historic Downtown Pass A Grille

4 out of 5

Save 100% on your flight

Price was $1,599, price is now $1,055 per person

$1,055

per person

Jan 5 - Jan 11

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

Stay at this aparthotel in St. Pete Beach. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Fort De Soto Park and Merry Pier are located nearby.

A six page contract with a ton of strict rules can’t move furniture, can’t touch tv, can’t leave sand in any place, leave a/c at 78 degrees etc etc., all these subject to fines. My a/c was pouring water all night and was fixed next morning. There is nobody at the hotel you can reach, that’s why everything is virtual. I don’t recommend it if you are looking for a relax vacation.

Reviewed on Jun 18, 2026

The Avalon Club

4 out of 5

Save 100% on your flight

Price was $1,533, price is now $1,012 per person

$1,012

per person

Nov 25 - Nov 28

found 8 hours ago

Roundtrip flight included

Atlanta (ATL) to Tampa (TPA)

Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Anna Maria Beach Resort

3.5 out of 5

Save 100% on your flight

Price was $2,611, price is now $1,729 per person

$1,729

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