Search Deals onParadise Key Vacation Packages
Paradise Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $754, price is now $499 per person
$499
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop 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.
Saddlebrook Resort
Wesley Chapel South
Save 100% on your flight
Price was $1,849, price is now $994 per person
$994
per person
Feb 14 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this spa resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $1,226, price is now $768 per person
$768
per person
Jan 30 - Feb 3
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 Lido Beach and Siesta Key Beach are located nearby.
Kompose Boutique Hotel
Save 100% on your flight
Price was $851, price is now $566 per person
$566
per person
Jan 30 - Feb 4
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 free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.
Pier House 60 Clearwater Beach Marina Hotel
Save 100% on your flight
Price was $999, price is now $671 per person
$671
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a rooftop terrace, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Clearwater Beach and Sand Key Park are located nearby.
Pelican Pointe Clearwater Beach Hotel
Save 100% on your flight
Price was $751, price is now $517 per person
$517
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, laundry facilities, and cable TV channels. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sand Key Park and Clearwater Beach are located nearby.
Hampton Inn Sarasota - I-75 Bee Ridge
Save 100% on your flight
Price was $767, price is now $539 per person
$539
per person
Feb 10 - Feb 14
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Sarasota. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Mall at University Town Center and Bent Tree Country Club are located nearby.
The Avalon Club
Save 100% on your flight
Price was $2,982, price is now $2,130 per person
$2,130
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Sand Key Park 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
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 ...
Island Grand at TradeWinds
5500 Gulf Blvd St. Pete Beach FL
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Hilton St. Petersburg Bayfront
333 1st St S St. Petersburg FL
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful ...
Sirata St. Pete Beach
5300 Gulf Blvd St. Pete Beach FL
Book a stay at this beach resort in St. Pete Beach. Enjoy 2 outdoor pools, 3 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
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 ...
The Don CeSar
3400 Gulf Boulevard St. Pete Beach FL
Book a stay at this beach hotel in St. Pete Beach. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Sunset Vistas Two Bedroom Beachfront Suites
12000 Gulf Blvd Treasure Island FL
Book a stay at this beach condo in Treasure Island. Enjoy 2 outdoor pools, a beach locale, and 2 hot tubs. Our guests praise the pool and the helpful staff in ...
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.
Sun, Jan 18 - Sat, Jan 24
ORD
O'Hare Intl.
TPA
Tampa Intl.
$68 Roundtrip, found 4 hours ago
$68
Roundtrip
found 4 hours ago
Mon, Jan 19 - Fri, Jan 23
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$69 Roundtrip, found 3 hours ago
$69
Roundtrip
found 3 hours ago
Tue, Feb 10 - Thu, Feb 12
CLE
Hopkins Intl.
TPA
Tampa Intl.
$70 Roundtrip, found 3 days ago
$70
Roundtrip
found 3 days ago
Wed, Jan 14 - Fri, Jan 16
JFK
John F. Kennedy Intl.
TPA
Tampa Intl.
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
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