Paradise Key Vacation Packages for 2026

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Top Hotel Deals

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
6.39 km from Paradise Key
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

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
20.59 km from Paradise Key
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 ...
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
5500 Gulf Blvd St. Pete Beach FL
6.02 km from Paradise Key
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 ...
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
333 1st St S St. Petersburg FL
13.06 km from Paradise Key
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 Beach Resort St Pete Beach

Sirata Beach Resort St Pete Beach

3.5 out of 5
5300 Gulf Boulevard St. Pete Beach FL
5.71 km from Paradise Key
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 ...
The Don CeSar

The Don CeSar

4 out of 5
3400 Gulf Boulevard St. Pete Beach FL
3.69 km from Paradise Key
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 ...
SkyBeach Resort

SkyBeach Resort

4 out of 5
6800 Sunshine Skyway Lane St. Petersburg FL
5.11 km from Paradise Key
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Pass-a-Grille Beach and Upham ...
Bilmar Beach Resort

Bilmar Beach Resort

4 out of 5
10650 Gulf Blvd Treasure Island FL
10.97 km from Paradise Key
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 Beachcomber

The Beachcomber

2.5 out of 5
6200 Gulf Blvd St. Pete Beach FL
6.53 km from Paradise Key
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 ...
Hyatt Place St. Petersburg / Downtown

Hyatt Place St. Petersburg / Downtown

3.5 out of 5
25 2nd Street North St. Petersburg FL
13.32 km from Paradise Key
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast ...
Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa

4 out of 5
77 11th St N St. Petersburg FL
12.46 km from Paradise Key
Book a stay at this business-friendly aparthotel in St. Petersburg. Enjoy free WiFi, valet parking (surcharge), and a picnic area. Our guests praise the helpful ...
Moxy St. Petersburg Downtown

Moxy St. Petersburg Downtown

3 out of 5
1234 Central Avenue St. Petersburg FL
12.28 km from Paradise Key
Stay at this hotel in St. Petersburg. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Popular attractions Salvador Dali Museum and Vinoy Park are located ...
Treasure Island Hotel and Marina

Treasure Island Hotel and Marina

3 out of 5
11125 Gulf Blvd Treasure Island FL
11.38 km from Paradise Key
Book a stay at this business-friendly hotel in Treasure Island. Enjoy free WiFi, a marina, and a rooftop terrace. Our guests praise the helpful staff and the ...
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
5450 Bollettieri Blvd. Bradenton FL
28.32 km from Paradise Key
Book a stay at this golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Hollander Boutique Hotel

Hollander Boutique Hotel

3 out of 5
421 4th Ave N St. Petersburg FL
13.49 km from Paradise Key
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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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

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.

Frontier Airlines
Sat, Sep 26 - Thu, Oct 1
PHL
Philadelphia Intl.
TPA
Tampa Intl.
$96 Roundtrip, found 5 days ago
$96
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Philadelphia Intl. to Tampa Intl., returning Thu, Oct 1, priced at $96 found 5 days ago
Delta
Tue, Aug 18 - Tue, Sep 1
JFK
John F. Kennedy Intl.
TPA
Tampa Intl.
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 18 from John F. Kennedy Intl. to Tampa Intl., returning Tue, Sep 1, priced at $157 found 1 hour ago
United
Wed, Sep 9 - Sat, Sep 19
EWR
Newark Liberty Intl. Airport
TPA
Tampa Intl.
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Sep 9 from Newark Liberty Intl. Airport to Tampa Intl., returning Sat, Sep 19, priced at $157 found 1 hour ago
American Airlines
Tue, Sep 22 - Wed, Sep 23
ORD
O'Hare Intl.
TPA
Tampa Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 22 from O'Hare Intl. to Tampa Intl., returning Wed, Sep 23, priced at $193 found 1 day ago
Southwest Airlines
Tue, Jul 28 - Mon, Aug 10
MDW
Midway Intl.
TPA
Tampa Intl.
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Jul 28 from Midway Intl. to Tampa Intl., returning Mon, Aug 10, priced at $200 found 5 days ago