Search Deals onSiesta Key Vacation Packages
Siesta Key Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Tampa Westshore - Airport Area by IHG
Price was $555, price is now $343 per person
$343
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.
Clean room
Reviewed on Nov 8, 2026
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $1,146, price is now $684 per person
$684
per person
Jan 11 - Jan 16
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.
CW Resort
Price was $1,482, price is now $903 per person
$903
per person
Jan 26 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Super clean, very helpful. Room was amazing and large. Onsite cafe had a very good brunch right on the intercoastal side. Well worth it. Short walk to beach (2-blocks) and restaurants.
Reviewed on Nov 9, 2026
Crystal Palms Beach Resort
Price was $1,207, price is now $751 per person
$751
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy a 24-hour front desk, dry cleaning or laundry services, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
It was amazing I felt like I got a whole apartment In one . It’s literally across the street from the beach 2-5 min walk you can see the water from hotel. It has a pool and hot tub .Everything was clean, the check in to get the keys in a lock box was different but I didn’t mind it . It felt like top secret underground location lol. 15/10 rating
Reviewed on Nov 7, 2026
Pescador Pool and Spa Home
Price was $1,563, price is now $978 per person
$978
per person
Jan 26 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this vacation home in Seminole. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions St. Petersburg - Clearwater Beaches and John's Pass Village & Boardwalk are located nearby.
Hibiscus Suites - Gateway to Siesta Key
Price was $1,656, price is now $1,040 per person
$1,040
per person
Jan 29 - Feb 6
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The place is so relaxed and everything looks good and clean. The pool is so nice. I like how the rooms have some kitchen tools we can use if don’t feel like dining outside. Will come back soon!
Reviewed on Nov 9, 2026
The Avalon Club
Price was $1,376, price is now $865 per person
$865
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Sailport Waterfront Suites
Price was $692, price is now $435 per person
$435
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Tampa. Enjoy breakfast (surcharge), a fitness center, and a 24-hour front desk. Our guests praise the pool and the restaurant in our reviews. Popular attractions Raymond James Stadium and George M. Steinbrenner Field 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 - Wed, Feb 3
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Tue, Jan 19 - Tue, Feb 2
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Tue, Jan 5 - Sat, Jan 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Tue, Dec 29 - Tue, Jan 5
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$289 Roundtrip, just found
$289
Roundtrip
just found
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