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.
  • Jul 24 - Jul 29

    Mar Bay Motel &Suites + Flight

    Safety Harbor
    5 nights
    2.0 star property
    8.6/10 - Excellent (79 reviews)
    "Great for older people who want an easily accessible room in a quiet setting. We will be back!"
    Reviewed May 7, 2026
    Roundtrip Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA1 stop TPA - YYZ1 stop
    CA $1,157
    CA $749
    per traveller
    found 1 day ago
    Mar Bay Motel &Suites
  • Aug 1 - Aug 8

    CW Hotel + Flight

    Clearwater Beach
    7 nights
    2.0 star property
    Roundtrip Montreal (YUL) - Tampa (TPA)
    YUL - TPANonstop TPA - YULNonstop
    CA $3,434
    CA $2,049
    per traveller
    found 1 day ago
    CW Hotel
  • Aug 17 - Aug 24

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    7 nights
    4.0 star property
    9.6/10 - Exceptional (1,007 reviews)
    "The view from the balcony is spectacular."
    Reviewed June 9, 2026
    Roundtrip Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA1 stop TPA - YYZ1 stop
    CA $2,090
    CA $1,330
    per traveller
    found 21 hours ago
    Ocean Club Treasure Island Hotel
  • Aug 1 - Aug 8

    The Avalon Club + Flight

    Clearwater Beach
    7 nights
    4.0 star property
    9.4/10 - 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, 2026
    Roundtrip Montreal (YUL) - Tampa (TPA)
    YUL - TPANonstop TPA - YULNonstop
    CA $4,734
    CA $3,242
    per traveller
    found 1 day ago
    The Avalon Club
  • Aug 14 - Aug 22

    The Barrymore Hotel Tampa Riverwalk + Flight

    Downtown Tampa
    8 nights
    3.0 star property
    8.6/10 - 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, 2026
    Roundtrip Montreal (YUL) - Tampa (TPA)
    YUL - TPA1 stop TPA - YUL1 stop
    CA $2,159
    CA $1,486
    per traveller
    found 1 day ago
    The Barrymore Hotel Tampa Riverwalk

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

Paradise Key Hotel Deals

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 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

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 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

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 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

Island Grand at TradeWinds
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

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.