Paradise Island Vacations from $673
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The Latest Paradise Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $1,045, price is now $673 per person
$673
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
Great area and transportation from hotel
Reviewed on Sep 29, 2025
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,192, price is now $686 per person
$686
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
Great location, great staff, it was a little noisy in the morning. You can hear the house keeping moving things around, but besides that the place was great. Newly renovated, right in the beach, nice pool area and the bartender was very nice and provided us information on everything we needed!
Reviewed on Sep 29, 2025
Embassy Suites by Hilton Sarasota, FL
Central Sarasota
Save 100% on your flight
Price was $1,327, price is now $844 per person
$844
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (1,613 reviews)
Pros: Property is clean and great rooms and breakfast! Check in employees are great. The $40 parking fee daily is a bit ridiculous and with the $28 destination fee....they really hike up the pirce of this place :( also the pool closing at sundown sucks am
nd if your traveling with big group hard to find a place you can all sit together other than resatraunt and they kick you out afer they close
Reviewed on Sep 29, 2025
Plaza Beach Hotel Beachfront Resort
Save 100% on your flight
Price was $1,156, price is now $748 per person
$748
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (1,010 reviews)
It was great with great help from the staff!
Reviewed on Sep 28, 2025
Where to stay in Paradise Island
Find the best Paradise Island areas and neighborhoods for the activities you enjoy most. Learn more about Paradise Island
Downtown St. Petersburg
1 out of top 10 points of interest in this area
Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.
Paradise Island Hotel Deals
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $231 total per night from Oct 7 to Oct 8
$231 total
Oct 7 - Oct 8
Total with taxes and fees
8/10 Very Good! (2,232 reviews)
"All"
Reviewed on Sep 29, 2025
Hilton St. Petersburg Bayfront
333 1st St S, St. Petersburg, FL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $133 total per night from Oct 12 to Oct 13
$133 total
Oct 12 - Oct 13
Total with taxes and fees
7.6/10 Good! (1,027 reviews)
"The vallet parking is pricy at $45 a day. The hotel doesn’t have any self parking area or options."
Reviewed on Sep 27, 2025
Wyndham Grand Clearwater Beach
100 Coronado Drive, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$340 nightly
The price is $384 total per night from Oct 20 to Oct 21
$384 total
Oct 20 - Oct 21
Total with taxes and fees
9.2/10 Wonderful! (2,699 reviews)
"Everyone was amazing"
Reviewed on Sep 23, 2025
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.
Discover the most popular places to visit in Paradise Island
John's Pass Village & Boardwalk
When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the marina in this family-friendly area, or check out its top-notch restaurants.
Clearwater Beach
Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.
St. Petersburg - Clearwater Beaches
Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?
Things to do
Sunset Celebration Cruise on Tropics Boat Tours
$32
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
$32
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
$35
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.