Paradise Island Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Paradise Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Clearwater Beach S-Harbourside by IHG
Price was $631, price is now $498 per person
$498
per person
Feb 8 - Feb 12
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this family-friendly hotel in Indian Rocks Beach. Enjoy free WiFi, a marina, and 3 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions St. Petersburg - Clearwater Beaches and Sand Key Park are located nearby.
The hotel is in an excellent location and staff were very friendly and helpful.
Reviewed on Nov 13, 2026
CW Resort
Price was $1,498, price is now $1,001 per person
$1,001
per person
Feb 8 - Feb 12
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.
New construction, clean everywhere. Great staff. Very happy have already rebooked
Reviewed on Nov 13, 2026
The Avalon Club
Price was $1,616, price is now $1,151 per person
$1,151
per person
Feb 8 - Feb 12
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Stay at this aparthotel in Clearwater Beach. Enjoy a fitness center, parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
Abode Beach House
Price was $930, price is now $692 per person
$692
per person
Feb 8 - Feb 12
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Pier 60 Park and Sand Key Park are located nearby.
Very nice rooms with a full small kitchenette. Everything was clean & the vibe was just perfect for my little 3 day getaway. Staff was friendly and helpful. Will visit again and will be recommending to my friends :-)
Reviewed on Nov 13, 2026
Oasis Palms
Sunshine Beach
Price was $752, price is now $592 per person
$592
per person
Feb 8 - Feb 12
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Stay at this hotel in Treasure Island. Enjoy free WiFi, free parking, and a picnic area. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
Island Grand at TradeWinds
Price was $999, price is now $788 per person
$788
per person
Feb 8 - Feb 12
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
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 in our reviews. Popular attractions John's Pass Village & Boardwalk and Tropicana Field are located nearby.
Amazing hotel for the family vacation
Reviewed on Nov 12, 2026
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See all available trips from Columbus to Paradise Island
View all tripsTop Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
24.21 km from Paradise Island
Book a stay at this beach hotel in Clearwater Beach. Enjoy a full-service spa, 3 restaurants, and a beach locale. Our guests praise the breakfast and the pool ...
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
24.06 km from Paradise Island
Book a stay at this beach resort in Clearwater Beach. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff ...
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
29.51 km from Paradise Island
Book a stay at this beach hotel in Tampa. Enjoy free WiFi, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
24.59 km from Paradise Island
Book a stay at this beach resort in Clearwater Beach. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Hotel South Tampa & Suites
3314 S Dale Mabry Hwy Tampa FL
30.03 km from Paradise Island
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 ...
The Westshore Grand, Tampa, A Tribute Portfolio Hotel
4860 West Kennedy Boulevard Tampa FL
30.4 km from Paradise Island
Book a stay at this business-friendly hotel in Tampa. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise the ...
RumFish Beach at TradeWinds
6000 Gulf Blvd St. Pete Beach FL
3.97 km from Paradise Island
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 ...
GALAXY HOTEL
101 3rd Ave N St. Petersburg FL
12.36 km from Paradise Island
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Popular attractions Tampa Bay ...
Shephard's Beach Resort
619 S Gulfview Blvd Clearwater Beach FL
23.33 km from Paradise Island
Book a stay at this beach hotel in Clearwater Beach. Enjoy free WiFi, free valet parking, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Fairfield Inn & Suites by Marriott Clearwater Beach
650 Bay Esplanade Clearwater Beach FL
25.5 km from Paradise Island
Book a stay at this business-friendly hotel in Clearwater Beach. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful ...
Grand Hyatt Tampa Bay
2900 Bayport Drive Tampa FL
30.31 km from Paradise Island
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean ...
Sailport Waterfront Suites
2506 N Rocky Point Dr Tampa FL
28.87 km from Paradise Island
Book a stay at this business-friendly aparthotel in Tampa. Enjoy breakfast (surcharge), a fitness center, and a 24-hour front desk. Our guests praise the pool ...
Hollander Boutique Hotel
421 4th Ave N St. Petersburg FL
11.97 km from Paradise Island
Book a stay at this spa hotel in St. Petersburg. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. ...
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See all available properties in Paradise Island
View all propertiesLowest 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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Jan 22 - Sat, Jan 30
DTW
Detroit Metropolitan Wayne County
TPA
Tampa Intl.
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Wed, Jan 13 - Sat, Jan 16
SWF
Stewart Intl.
TPA
Tampa Intl.
$178 Roundtrip, found 5 hours ago
$178
Roundtrip
found 5 hours ago
Sun, Dec 6 - Fri, Dec 18
MSP
Minneapolis - St. Paul Intl.
SRQ
Sarasota-Bradenton Intl.
$207 Roundtrip, found 6 hours ago
$207
Roundtrip
found 6 hours ago
Tue, Jan 19 - Sat, Jan 23
JFK
John F. Kennedy Intl.
TPA
Tampa Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Sat, Jan 9 - Sat, Jan 23
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago