Search Deals onParadise Key Vacation Packages
Paradise Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG
Central Sarasota
Price was $881, price is now $689 per person
$689
per person
Jan 3 - Jan 7
just found
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 St. Armands Circle and Lido Beach are located nearby.
Crystal Palms Beach Resort
Sunshine Beach
Price was $1,223, price is now $922 per person
$922
per person
Dec 22 - Dec 27
found 8 hours ago
Roundtrip non-stop 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.
Hibiscus Suites - Gateway to Siesta Key
Price was $2,159, price is now $1,634 per person
$1,634
per person
Dec 26 - Jan 3
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.
Cedar Cove Resort and Cottages
Price was $1,810, price is now $1,371 per person
$1,371
per person
Dec 22 - Dec 27
found 15 hours ago
Roundtrip non-stop 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.
John's Pass Hotel
Price was $1,473, price is now $1,134 per person
$1,134
per person
Dec 22 - Dec 27
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this aparthotel in Madeira Beach. Enjoy free WiFi, a marina, and 4 beach bars. Our guests praise the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Hotel South Tampa & Suites
Virginia Park
Price was $1,016, price is now $805 per person
$805
per person
Dec 22 - Dec 27
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tampa Riverwalk and Benchmark International Arena are located nearby.
Spark by Hilton Sarasota Siesta Key Gateway
Price was $1,979, price is now $1,570 per person
$1,570
per person
Dec 26 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Resort Sixty-Six
Price was $2,451, price is now $1,965 per person
$1,965
per person
Dec 26 - Jan 2
found 9 hours 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 beach locale. Popular attractions Bradenton Beach and Anna Maria Beach are located nearby.
3-4 Night Vacations in Paradise Key
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Paradise Key
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Paradise Key
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
RumFish Beach at TradeWinds
6000 Gulf Blvd St. Pete Beach FL
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 4 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
GALAXY HOTEL
101 3rd Ave N St. Petersburg FL
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Popular attractions Tampa Bay ...
Save an average of 15% on thousands of hotels when you're signed in
Extended Stay America Suites Clearwater Carillon Park
2311 Ulmerton Rd Clearwater FL
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hollander Boutique Hotel
421 4th Ave N St. Petersburg FL
Book a stay at this spa hotel in St. Petersburg. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. ...
The Don CeSar
3400 Gulf Boulevard St. Pete Beach FL
Book a stay at this beach resort in St. Pete Beach. Enjoy a full-service spa, 2 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
Ponce De Leon Hotel
95 Central Ave St. Petersburg FL
Stay at this hotel in St. Petersburg. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms ...
The Beachcomber
6200 Gulf Blvd St. Pete Beach FL
Book a stay at this beach hotel in St. Pete Beach. Enjoy 2 outdoor pools, a beach locale, and a nightclub. Our guests praise the helpful staff and the clean ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Jan 11 - Fri, Jan 15
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$78 Roundtrip, found 5 hours ago
$78
Roundtrip
found 5 hours ago
Mon, Jan 11 - Fri, Jan 15
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Sun, Jan 10 - Thu, Jan 14
TTN
Mercer
PIE
St. Petersburg-Clearwater Intl.
$83 Roundtrip, found 2 hours ago
$83
Roundtrip
found 2 hours ago
Wed, Feb 3 - Thu, Feb 4
CLE
Hopkins Intl.
TPA
Tampa Intl.
$84 Roundtrip, found 21 hours ago
$84
Roundtrip
found 21 hours ago
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