Search Deals onParadise Key Vacation Packages
Paradise Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort
Wesley Chapel South
Price was $783, price is now $555 per person
$555
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Austin (AUS) to Tampa (TPA)
Book a stay at this golf resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $1,352, price is now $898 per person
$898
per person
Sep 9 - Sep 13
found 21 hours 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 Coquina Beach and Bean Point Beach are located nearby.
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,179, price is now $796 per person
$796
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop 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 Hotel
Save 100% on your flight
Price was $1,160, price is now $793 per person
$793
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop 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 Clearwater Beach and Pier 60 Park are located nearby.
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $927, price is now $646 per person
$646
per person
Aug 28 - Sep 3
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
The Hotel Zamora
Save 100% on your flight
Price was $1,160, price is now $824 per person
$824
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Fort De Soto Park and John's Pass Village & Boardwalk are located nearby.
The Fold Hotels Indian Shores
Save 100% on your flight
Price was $1,052, price is now $763 per person
$763
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
Book a stay at this beach aparthotel in Indian Shores. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Petersburg - Clearwater Beaches and John's Pass Village & Boardwalk are located nearby.
Twin Palms at Siesta
Save 100% on your flight
Price was $958, price is now $709 per person
$709
per person
Aug 30 - Sep 5
found 1 hour ago
Roundtrip flight included
Trenton (TTN) to Tampa (TPA)
Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and private pools. Our guests praise the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido 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
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 4 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 ...
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 ...
Sirata St. Pete Beach Resort, Tapestry Collection by Hilton
5300 Gulf Boulevard St. Pete Beach FL
Book a stay at this beach hotel in St. Pete Beach. Enjoy an outdoor pool, a beach locale, and breakfast (surcharge). Popular attractions John's Pass Village ...
Bilmar Beach Resort
10650 Gulf Blvd Treasure Island FL
Book a stay at this beach resort in Treasure Island. Enjoy free WiFi, free parking, and 2 outdoor pools. 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.
Wed, Sep 23 - Wed, Sep 30
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$68 Roundtrip, found 5 hours ago
$68
Roundtrip
found 5 hours ago
Thu, Oct 1 - Thu, Oct 15
TTN
Mercer
PIE
St. Petersburg-Clearwater Intl.
$78 Roundtrip, found 5 hours ago
$78
Roundtrip
found 5 hours ago
Fri, Oct 16 - Fri, Nov 6
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$78 Roundtrip, found 17 hours ago
$78
Roundtrip
found 17 hours ago
Sat, Aug 29 - Wed, Sep 2
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
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