A boat on calm waters during sunset with a clear sky.

Bay Harbor Estates Vacations from $690

Book a Hotel + Flight or Car together to unlock savings

Your Bay Harbor Estates Vacation

Make travel planning stress-free by creating a vacation package to Bay Harbor Estates. We'll take care of the minutiae, so you can focus on savoring everything this neighborhood can offer. Begin your trip to Bay Harbor Estates by heading to nearby attractions such as Englewood Beach, Stump Pass Beach State Park and Englewood Recreation Center. No matter your travel plans or budget, booking the ultimate Bay Harbor Estates vacation has never been easier with Expedia.

The Latest Bay Harbor Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern building entrance with glass doors, a dark exterior, and potted plants on the sides.
    Jan 21 - Jan 25

    Wiggins Pass Chalet + Flight

    Naples
    4 nights
    4.0 star property
    9.6/10 - Exceptional (301 reviews)
    "Staff were super helpful."
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $984
    $690
    per traveler
    found 1 day ago
    Wiggins Pass Chalet
  • A pool area with lounge chairs and umbrellas, surrounded by palm trees.
    Jan 21 - Jan 25

    The Perry Hotel Naples + Flight

    Naples
    4 nights
    4.5 star property
    9.6/10 - Exceptional (1,258 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $1,958
    $1,261
    per traveler
    found 1 day ago
    The Perry Hotel Naples
  • A balcony with a view of the beach, white railings, and a lounge chair with towels.
    Jan 21 - Jan 25

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

    Vanderbilt Beach
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Great resort. Probably the nicest on the entire run of resorts on this beach. And that includes the Ritz-Carlton just upo the way. Obviously, the Ritz is classier, but La Playa felt more exclusive and comfortable. The beach experience is top-notch, with complimentary umbrellas and beach chairs upon request. The bar and restaurant were very good. Drinks are pricey, to be sure, which can add up if you're ordering while relaxing on the beach for days on end. About a 25 minute drive to the best..."
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $3,486
    $2,320
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • A balcony with a view of the beach and ocean.
    Jan 27 - Jan 31

    Manasota Key Resort + Flight

    Manasota Key
    4 nights
    2.5 star property
    9.6/10 - Exceptional (342 reviews)
    "We loved our stay. Thank you so much for the great hospitality"
    Reviewed October 22, 2026
    Roundtrip • Detroit (DTW) - Fort Myers (RSW)
    DTW - TPA • Nonstop TPA - DTW • Nonstop
    Save 100% on your flight
    $1,142
    $765
    per traveler
    found 4 hours ago
    Manasota Key Resort
  • A beach with a thatched-roof structure, palm trees, and a view of the sea.
    Dec 17 - Dec 20

    The Suites at Fishermen’s Village + Flight

    Punta Gorda Isles
    3 nights
    3.0 star property
    9.8/10 - Exceptional (1,366 reviews)
    "Everything well"
    Reviewed November 9, 2026
    Roundtrip • Detroit (DTW) - Fort Myers (RSW)
    DTW - RSW • Nonstop RSW - DTW • Nonstop
    $975
    $692
    per traveler
    found 1 day ago
    The Suites at Fishermen’s Village

Where to stay in Bay Harbor Estates

Find the best Bay Harbor Estates areas and neighborhoods for the activities you enjoy most.
A sunset over the ocean with waves and a fallen tree on the beach.

Manasota Key

A sunset over a beach with waves lapping onto the shore and silhouettes of people in the distance.

Manasota Beach

If you're spending some time in Manasota Beach, Manasota Beach and Blind Pass Beach are top sights worth seeing.

A coastal residential area with a beach, roads, and a marina.

Manasota

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

Englewood Central

While Englewood Central isn't home to many top sights, Lemon Bay and Lemon Bay Playhouse are some notable places to visit nearby.

A beach at sunset with tall grasses in the foreground and people in the background.

Olde Englewood Village

While visiting Olde Englewood Village, you might make a stop by sights like Lemon Bay and Lemon Bay Playhouse.

Bay Harbor Estates Hotel Deals

A hotel room with a large bed, two bedside lamps, a nightstand, a mirror, and a curtain.

Sun Coast Inn

Sun Coast Inn
2.5 star property
Englewood South, 0.3 mi from Bay Harbor Estates
8.0 out of 10, Very good, (1,002 reviews)
"We stayed for 2 nights because my son was getting married. He referred us to this Inn and we were so pleasantly surprised for how clean it was. It was in a perfect location to get to the beach for his wedding. I highly recommend Sun Coast Inn for your next visit. Enjoy!"
$72 nightly
The price is $81
Nov 11 - Nov 12
Total with taxes and fees
Sun Coast Inn
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 Bay Harbor Estates
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.