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A small island with Spanish moss-covered trees surrounded by calm water.

Shady Hills Vacations from $660

Book a Hotel + Flight or Car together to unlock savings

The Latest Shady Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • 2 outdoor pools, cabanas (surcharge), pool umbrellas
    Oct 4 - Oct 10

    Saddlebrook Resort + Flight

    Wesley Chapel South
    6 nights
    4.0 star property
    8.0/10 - Very Good (143 reviews)
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • 1 stop
    Save 100% on your flight
    $982
    $660
    per traveler
    found 1 day ago
    Saddlebrook Resort
  • 2 bedrooms, memory foam beds, in-room safe, blackout drapes
    Oct 14 - Oct 19

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,111 reviews)
    "The two bedroom unit is large. I thought it was clean but my niece and kids said the entrance smelled like mildew. So I held the door open for fresh air to circulate. The master bedroom mattress was uneven/worn out. Everything else was nice. I enjoyed the patio area. I love how spacious the unit and patio area. I enjoyed my beach front stay."
    Reviewed July 27, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • 1 stop
    Save 100% on your flight
    $1,430
    $873
    per traveler
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • Exterior
    Sep 14 - Sep 17

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    3 nights
    3.0 star property
    9.2/10 - Wonderful (563 reviews)
    "Everything was amazing from the moment I walked in to the office for check in, the staff was friendly, helpful and informative! This was a home away from home! I will definitely be back next year!"
    Reviewed July 26, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - SRQ • 1 stop SRQ - BOS • 1 stop
    Save 100% on your flight
    $1,030
    $663
    per traveler
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Living area
    Oct 14 - Oct 19

    CW Hotel + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.6/10 - Exceptional (29 reviews)
    "** Caution to EXPENSIVE servce CHARGE ** Nice place, big appartment. New hotel. Room was not clening well, lot of hair in the bath and towel from last renter in the washer machine. I was surprise to be charge a 500$$$ extra services fee, not advertising on Hotel.com. Oven and cook top is RV size, not apropriate for a family. Big living room but only a small love seats and a chair. Not appropriate for a family maybe need more furniture. The elevator is very slow and the staff use it in the..."
    Reviewed July 26, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • 1 stop
    Save 100% on your flight
    $1,231
    $794
    per traveler
    found 1 day ago
    CW Hotel
  • Property amenity
    Oct 19 - Oct 25

    The Westin Sarasota + Flight

    Central Sarasota
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,162 reviews)
    "I prefer to use a hotel that has housekeepers who can speak English and NOT ask me of I can speak Spanish after I've posed a question they can't comprehend."
    Reviewed July 26, 2026
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    Save 100% on your flight
    $1,391
    $950
    per traveler
    found 1 day ago
    The Westin Sarasota
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.