A coastal scene with a lighthouse, beach, and ocean.

Tradewinds Vacations from $1,088

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Your Tradewinds Vacation

Booking a tailor-made Tradewinds vacation package is a great way to become familiar with this unique neighborhood. From its hot spots to its little-known gems, there's plenty to discover. Kick start your trip to Tradewinds by heading to nearby attractions such as Sanibel Island Southern Beach, Bowmans Beach and J. N. Ding Darling National Wildlife Refuge. Whatever your travel plans or the size of your budget, booking your perfect Tradewinds vacation is easy with Expedia.

The Latest Tradewinds Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A cozy outdoor seating area with a white bench and potted plants, a sign for 'Bijoux' gelateria, and a brick pathway.
    Jan 11 - Jan 17

    Olde Marco Island Inn and Suites + Flight

    Olde Marco
    6 nights
    3.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Very nice place to stay when visiting Marco Island . 2nd time staying at old Marco inn and suites Nice place, fair price, completely satisfied and will certainly go back again in the future"
    Reviewed October 27, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop RSW - BOS • 1 stop
    Save 100% on your flight
    $1,537
    $1,088
    per traveler
    found 1 day ago
    Olde Marco Island Inn and Suites
  • A balcony with a view of the beach, white railings, and a lounge chair with towels.
    Jan 23 - Jan 29

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

    Vanderbilt Beach
    6 nights
    4.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Wonderful resort. Every staff member was pleasant and helpful. The property was very clean and there are plenty of on site amenities within a short walk. Would highly recommend."
    Reviewed November 3, 2026
    Roundtrip • New York (EWR) - Fort Myers (RSW)
    EWR - RSW • Nonstop RSW - EWR • Nonstop
    $4,920
    $3,133
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • A pool area with lounge chairs and umbrellas, surrounded by palm trees.
    Jan 23 - Jan 29

    The Perry Hotel Naples + Flight

    Naples
    6 nights
    4.5 star property
    9.6/10 - Exceptional (1,249 reviews)
    Roundtrip • New York (EWR) - Fort Myers (RSW)
    EWR - RSW • Nonstop RSW - EWR • Nonstop
    $2,296
    $1,473
    per traveler
    found 1 day ago
    The Perry Hotel Naples
  • A poolside area with a sofa, lounge chairs, a fire pit, and a view of a tropical garden.
    Jan 11 - Jan 17

    A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave + Flight

    Naples
    6 nights
    3.0 star property
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop RSW - BOS • 1 stop
    Save 100% on your flight
    $2,933
    $2,076
    per traveler
    found 1 day ago
    A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave
  • A modern kitchen with granite countertops, a central island with fruit, and a view of a swimming pool.
    Jan 17 - Jan 22

    Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples + Flight

    Bonita Springs
    5 nights
    3.0 star property
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop RSW - BOS • Nonstop
    Save 100% on your flight
    $2,424
    $1,717
    per traveler
    found 1 day ago
    Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Where to stay in Tradewinds

Find the best Tradewinds areas and neighborhoods for the activities you enjoy most.
A coastal scene with a lighthouse, beach, and ocean.

Mid Island

While visiting Mid Island, you might make a stop by sights like Periwinkle Way and Sanibel Island Southern Beach.

A coastal scene with a lighthouse, beach, and ocean.

West End

While visiting West End, you might make a stop by sights like J. N. Ding Darling National Wildlife Refuge and Bowman's Beach.

A coastal scene with a lighthouse, beach, and ocean.

East End

While visiting East End, you might make a stop by sights like Sanibel Island Northern Beach and Sanibel Island Lighthouse.

A street lined with palm trees and a sign for Periwinkle Place Shops.

Beachview Country Club Estates

If you're spending some time in Beachview Country Club Estates, Periwinkle Way and Sanibel Island Golf Club are top sights worth seeing.

Sanctuary

While Sanctuary might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Blind Pass Beach and Turner Beach.

Tradewinds Hotel Deals

A beach with a variety of seashells and pebbles.

Sanibel Island Beach Resort

Sanibel Island Beach Resort
3.0 star property
Mid Island, 6 mi from Tradewinds
9.2 out of 10, Wonderful, (2,401 reviews)
$224 nightly
The price is $250
Nov 5 - Nov 6
Total with taxes and fees
Sanibel Island Beach Resort
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 Tradewinds
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.