Search Deals onParadise Key Vacation Packages
Paradise Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
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.
Saddlebrook Resort
Wesley Chapel South
Save 100% on your flight
Price was $1,422, price is now $697 per person
$697
per person
Jan 29 - Feb 5
found 1 day ago
Roundtrip 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 $1,658, price is now $1,071 per person
$1,071
per person
Feb 13 - Feb 18
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.
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $1,151, price is now $755 per person
$755
per person
Feb 13 - Feb 18
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.
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,127, price is now $749 per person
$749
per person
Jan 25 - Jan 31
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.
The Beach Haven Resort
Save 100% on your flight
Price was $851, price is now $580 per person
$580
per person
Jan 25 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in St. Pete Beach. Enjoy free parking, a beach locale, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and Polynesian Putter are located nearby.
The Hotel Zamora
Save 100% on your flight
Price was $1,251, price is now $864 per person
$864
per person
Jan 25 - Jan 31
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 John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.
Residence Inn by Marriott Sarasota Bradenton
Bayou Oaks
Save 100% on your flight
Price was $1,048, price is now $727 per person
$727
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Lido Beach and St. Armands Circle 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.
Mon, Jan 19 - Fri, Jan 23
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$63 Roundtrip, found 14 hours ago
$63
Roundtrip
found 14 hours ago
Tue, Feb 10 - Tue, Feb 10
CLE
Hopkins Intl.
TPA
Tampa Intl.
$64 Roundtrip, found 2 days ago
$64
Roundtrip
found 2 days ago
Sun, Jan 18 - Sat, Jan 24
ORD
O'Hare Intl.
TPA
Tampa Intl.
$68 Roundtrip, found 17 hours ago
$68
Roundtrip
found 17 hours 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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