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A sunset over the ocean with waves and a fallen tree on the beach.

Manasota Key Vacations from $688

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The Latest Manasota Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Private beach, surfing, kayaking, rowing
    Sep 14 - Sep 17

    Manasota Key Resort + Flight

    Manasota Key
    3 nights
    2.5 star property
    9.4/10 - Exceptional (305 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop RSW - PSM • 1 stop
    $997
    $688
    per traveler
    found 1 day ago
    Manasota Key Resort
  • View from room
    Oct 9 - Oct 13

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,002 reviews)
    "We love laplaya and go there 1-2 x a year. Beach is always amazing w great beach and wait staff! Food at bakery is delicious!"
    Reviewed July 29, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    Save 100% on your flight
    $1,868
    $1,179
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • Luxury House, Pool View | Pool | Outdoor pool
    Sep 7 - Sep 12

    A Wave From it All + Flight

    Siesta Isle
    5 nights
    2.0 star property
    Roundtrip • Minneapolis (MSP) - Fort Myers (RSW)
    MSP - RSW • Nonstop RSW - MSP • 1 stop
    Save 100% on your flight
    $2,271
    $1,447
    per traveler
    found 1 day ago
    A Wave From it All
  • 2 outdoor pools, cabanas (surcharge), pool umbrellas
    Oct 9 - Oct 13

    The Perry Hotel Naples + Flight

    Naples
    4 nights
    4.5 star property
    9.6/10 - Exceptional (980 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    $1,155
    $781
    per traveler
    found 1 day ago
    The Perry Hotel Naples
  • Village Beach & Harbor Suite | Balcony view
    Sep 3 - Sep 8

    The Suites at Fishermen’s Village- 2 Bedroom Suites + Flight

    Punta Gorda Isles
    5 nights
    3.0 star property
    9.8/10 - Exceptional (1,277 reviews)
    "The property was very clean. Kitchen was stocked with dishes, pots and pans, utensils and everything we could want. The beds and pillows were comfortable. Ceiling fans were in every room. Couch and chair was clean and comfortable. TVs in every room. Centrally located. Easy to access."
    Reviewed July 30, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop RSW - BOS • 1 stop
    Save 100% on your flight
    $1,073
    $732
    per traveler
    found 1 day ago
    The Suites at Fishermen’s Village- 2 Bedroom Suites

Manasota Key Hotel Deals

Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key, 0.2 mi from Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Clean and nice place. The manager was super nice and attentive. And the beach is just across the street! We definitely enjoyed our stay."
$499 nightly
The price is $535
Aug 2 - Aug 3
Total with taxes and fees
Chadwick Cove Resort & Marina
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.
See all properties in Manasota Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.