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 $1,234, price is now $783 per person
$783
per person
Dec 1 - Dec 8
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.
Siesta Key Inn
South Village
Save 100% on your flight
Price was $1,517, price is now $904 per person
$904
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $1,646, price is now $999 per person
$999
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip 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.
Azul Resort
South Village
Save 100% on your flight
Price was $1,744, price is now $1,083 per person
$1,083
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Tropical Breeze Resort
Siesta Key Village
Save 100% on your flight
Price was $1,262, price is now $792 per person
$792
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Siesta Palms By the Beach
South Village
Save 100% on your flight
Price was $1,912, price is now $1,201 per person
$1,201
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,921, price is now $1,213 per person
$1,213
per person
Dec 1 - Dec 8
found 1 day 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 Lido Beach and Siesta Key Beach are located nearby.
Anna Maria Beach Resort
Save 100% on your flight
Price was $2,872, price is now $1,870 per person
$1,870
per person
Nov 18 - Nov 23
found 1 day 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 private beach. Our guests praise the pool and the helpful staff in our reviews. 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
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 ...
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 ...
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 valet parking (surcharge). Popular attractions Tampa ...
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 ...
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 ...
Barefoot Beach Club
13238 Gulf Blvd Madeira Beach FL
Book a stay at this beach hotel in Madeira Beach. Enjoy 2 outdoor pools, a beach locale, and a fitness center. 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 ...
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 ...
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, Nov 2 - Mon, Nov 16
PHL
Philadelphia Intl.
PIE
St. Petersburg-Clearwater Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Tue, Dec 1 - Fri, Dec 4
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$110 Roundtrip, found 1 hour ago
$110
Roundtrip
found 1 hour ago
Tue, Nov 17 - Wed, Dec 2
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$116 Roundtrip, found 3 hours ago
$116
Roundtrip
found 3 hours ago
Sat, Oct 31 - Thu, Nov 5
CLE
Hopkins Intl.
TPA
Tampa Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
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