Paradise Key Holidays

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Where to stay in Paradise Key

Find the best Paradise Key areas and neighborhoods for the activities you enjoy most. Learn more about Paradise Key
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

Downtown St. Petersburg is beloved for its fantastic nightlife. Take some time to explore sights in the area like Tampa Bay and Palladium Theater.

Find hotels in Downtown St. Petersburg

Top hotels in Paradise Key

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is 6.378.548 ₫ per night from 16 Feb to 17 Feb
6.378.548 ₫
8.821.547 ₫ total
16 Feb - 17 Feb
includes taxes & fees
8.2/10 Very Good! (1,623 reviews)
Room spotless staff was great

Reviewed on 8 Feb 2026

RumFish Beach at TradeWinds
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
The price is 6.052.675 ₫ per night from 16 Feb to 17 Feb
6.052.675 ₫
7.573.064 ₫ total
16 Feb - 17 Feb
includes taxes & fees
9.4/10 Exceptional! (1,945 reviews)
Shower water never hot enough

Reviewed on 12 Feb 2026

Compass Hotel by Margaritaville Anna Maria Sound
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
5500 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is 5.716.415 ₫ per night from 23 Feb to 24 Feb
5.716.415 ₫
8.073.349 ₫ total
23 Feb - 24 Feb
includes taxes & fees
7.4/10 Good! (1,005 reviews)
Restaurant & bar staff, service staff & Cabana beach service is outstanding ! Beach access is unmatched ! White flour soft sand ! However the Parking lot access to hotel was obstructed by several large service delivery trucks ! This is unacceptable & a very bad look ! This needs to be resolved! A ...

Reviewed on 6 Feb 2026

Island Grand at TradeWinds
See all 16,797 properties in Paradise Key
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.

Popular places to visit

Florida. Madeira Beach Florida. Gulf of Mexico or ocean beach, Hotels and Resorts. John's Pass Village and Boardwalk. Turquoise color of salt water. American shore. Summer or Autumn vacation.

John's Pass Village & Boardwalk

4/5(33 reviews)

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 visit its top-notch restaurants.

John's Pass Village & Boardwalk
Fort De Soto Park featuring a beach

Fort De Soto Park

4.5/5(25 reviews)

Enjoy the beautiful sunsets and explore Fort De Soto Park, a lovely green space in Tierra Verde. Discover the top-notch restaurants and great live music in this family-friendly area.

Fort De Soto Park
Salvador Dali Museum featuring night scenes and modern architecture

Salvador Dali Museum

5/5(20 reviews)

You can spend time browsing the exhibits at Salvador Dali Museum during your trip to St. Petersburg. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Salvador Dali Museum