Search Deals onParadise Key Vacation Packages
Paradise Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Golden Host Resort - Sarasota
North Trail
Price was $467, price is now $347 per person
$347
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lido Beach and Mote Marine Laboratory & Aquarium are located nearby.
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,938, price is now $1,224 per person
$1,224
per person
May 23 - May 30
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.
Mar Bay Motel &Suites
Save 100% on your flight
Price was $573, price is now $374 per person
$374
per person
May 17 - May 21
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Philippe Park and Safety Harbor Waterfront Park are located nearby.
Hotel South Tampa & Suites
Virginia Park
Save 100% on your flight
Price was $821, price is now $555 per person
$555
per person
May 18 - May 23
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Port of Tampa are located nearby.
The Avalon Club
Save 100% on your flight
Price was $2,125, price is now $1,535 per person
$1,535
per person
May 26 - May 31
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 Pier 60 are located nearby.
RumFish Beach at TradeWinds
Save 100% on your flight
Price was $1,190, price is now $868 per person
$868
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
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 our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.
Pelican Pointe Clearwater Beach Hotel
Save 100% on your flight
Price was $1,191, price is now $870 per person
$870
per person
May 23 - May 30
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 Pier 60 Park 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 ...
SkyBeach Resort
6800 Sunshine Skyway Lane St. Petersburg FL
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Salvador Dali Museum and Fort ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
SureStay Hotel by Best Western St. Pete Clearwater Airport
Clearwater FL
Book a stay at this business-friendly hotel in Clearwater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sirata Beach Resort St Pete Beach
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 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 ...
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, Apr 13 - Fri, May 1
TTN
Mercer
TPA
Tampa Intl.
$76 Roundtrip, found 4 hours ago
$76
Roundtrip
found 4 hours ago
Mon, Apr 13 - Fri, May 1
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$76 Roundtrip, found 4 hours ago
$76
Roundtrip
found 4 hours ago
Sat, Apr 18 - Fri, Apr 24
ORD
O'Hare Intl.
TPA
Tampa Intl.
$88 Roundtrip, just found
$88
Roundtrip
just found
Tue, Aug 11 - Tue, Aug 25
CLE
Hopkins Intl.
TPA
Tampa Intl.
$93 Roundtrip, just found
$93
Roundtrip
just found