Paradise Key Vacation Packages
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The Latest Paradise Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Mar Bay Motel &Suites
Jul 24 - Jul 29Mar Bay Motel &Suites + Flight
Safety Harbor5 nights8.6/10 - Excellent (79 reviews)"Great for older people who want an easily accessible room in a quiet setting. We will be back!"Reviewed May 7, 2026Roundtrip • Toronto (YYZ) - Tampa (TPA)YYZ - TPA • 1 stop TPA - YYZ • 1 stopCA $1,157CA $749found 1 day agoper traveller - Ocean Club Treasure Island Hotel
Aug 17 - Aug 24Ocean Club Treasure Island Hotel + Flight
Sunshine Beach7 nights9.6/10 - Exceptional (1,007 reviews)"The view from the balcony is spectacular."Reviewed June 9, 2026Roundtrip • Toronto (YYZ) - Tampa (TPA)YYZ - TPA • 1 stop TPA - YYZ • 1 stopCA $2,090CA $1,330found 21 hours agoper traveller - The Avalon Club
Aug 1 - Aug 8The Avalon Club + Flight
Clearwater Beach7 nights9.4/10 - Exceptional (554 reviews)"Great staff, everyone very pleasant, friendly and helpful. Super clean rooms and very comfy beds. Kitchen amenities perfect for cooking or preparing food. Laundry room a plus! Loved this place."Reviewed June 9, 2026Roundtrip • Montreal (YUL) - Tampa (TPA)YUL - TPA • Nonstop TPA - YUL • NonstopCA $4,734CA $3,242found 1 day agoper traveller - The Barrymore Hotel Tampa Riverwalk
Aug 14 - Aug 22The Barrymore Hotel Tampa Riverwalk + Flight
Downtown Tampa8 nights8.6/10 - Excellent (2,620 reviews)"Great downtown location near the Riverwalk. It was a short stay, but seemed to be a nice hotel"Reviewed June 9, 2026Roundtrip • Montreal (YUL) - Tampa (TPA)YUL - TPA • 1 stop TPA - YUL • 1 stopCA $2,159CA $1,486found 1 day agoper traveller
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
Pass-a-Grille
1 out of top 10 points of interest in this area
Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.
Paradise Key Hotel Deals
RumFish Beach at TradeWinds
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $262 per night from Jun 28 to Jun 29
CA $262
CA $383 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (2,023 reviews)
"Our only issue was that our room wasn’t cleaned until the second to the last day we were do to leave. I had spoken to a housekeeper during the middle of the week, who was at the room next door. I asked if she was stopping at our room next. She appeared to have said yes but no one showed. Later that ..."
Reviewed on Jun 9, 2026
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jun 16 to Jun 17
CA $212
CA $279 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (2,250 reviews)
"We enjoyed our stay, food and drinks were good. Only thing that could have been better is the pool service, serving food and drinks."
Reviewed on Jun 10, 2026
Island Grand at TradeWinds
5500 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $288 per night from Jun 28 to Jun 29
CA $288
CA $412 total
Jun 28 - Jun 29
includes taxes & fees
7.6/10 Good! (1,205 reviews)
"We loved this resort for our family vacation with our 5 year old son. The beach is huge & stunning & easy to walk in! He had a blast for hours on the slide. We also liked that we could have an umbrella and 2 beach chairs at no additional cost. We also ate way too many smores at nightly s’mores party! ..."
Reviewed on Jun 9, 2026
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 Key
John's Pass Village & Boardwalk
4.5/5(141 reviews)
When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its lively bars.
Clearwater Beach
4.5/5(5 reviews)
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.
Fort De Soto Park
4.5/5(28 reviews)
Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.
Things to do
Sunset Celebration Cruise on Tropics Boat Tours
CA $51
per adult
92% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
CA $51
per adult
90% of travellers recommend
Pirate Adventure Cruise - John's Pass
CA $62
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.