Search Deals onSiesta Key Vacation Packages
Siesta Key Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach
Save 100% on your flight
Price was $975, price is now $661 per person
$661
per person
Dec 31 - Jan 5
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
Staff was outstanding. Room was clean. It just wasn’t that wow factor of the room considering the price. But the view was amazing
Reviewed on Oct 24, 2026
CW Resort
Save 100% on your flight
Price was $1,755, price is now $1,051 per person
$1,051
per person
Dec 31 - Jan 5
found 16 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.
Beautiful place to stay
Reviewed on Oct 23, 2026
The Avalon Club
Save 100% on your flight
Price was $1,714, price is now $1,026 per person
$1,026
per person
Dec 31 - Jan 5
found 16 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.
Much more spacious than we expected. Very clean, entire staff were very friendly and knowledgeable. A nice scent was all over the hotel, a nice touch. Definitely would recommend this hotel.
Reviewed on Oct 23, 2026
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $2,403, price is now $1,553 per person
$1,553
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $1,482, price is now $988 per person
$988
per person
Dec 3 - Dec 7
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.
Awesome resort, highly recommend if visiting AMI. Great location and can use free island trolley to go anywhere you want.
Reviewed on Oct 24, 2026
Captiva Beach Resort
Save 100% on your flight
Price was $1,355, price is now $913 per person
$913
per person
Jan 15 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
La Tortuga Historic Downtown Pass A Grille
Save 100% on your flight
Price was $1,348, price is now $950 per person
$950
per person
Jan 14 - Jan 19
found 24 hours ago
Roundtrip flight included
Indianapolis (IND) 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.
Such a beautiful place!!! My only recommendation is they need to lock the gates at the pool! We left at 3:30 am and there were 3 people swimming in the pool… they took off running away when they saw us, so definitely not guests!!!
The property is so beautiful and well cared for that I’d hate to see someone destroy something!
Reviewed on Oct 18, 2026
voco Sarasota by IHG
Price was $2,297, price is now $1,633 per person
$1,633
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 St. Armands Circle and Lido Beach are located nearby.
Siesta Key Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Siesta Key Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Jan 19 - Tue, Feb 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Tue, Jan 5 - Sat, Jan 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Tue, Dec 1 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$200 Roundtrip, found 18 hours ago
$200
Roundtrip
found 18 hours ago
Sat, Jan 23 - Tue, Jan 26
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, found 22 hours ago
$219
Roundtrip
found 22 hours ago
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