Search Deals onThe Estates Vacation Packages
The Estates Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites
Price was $632, price is now $482 per person
$482
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Port Charlotte. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Deep Creek Golf Club and Lake Betty Park are located nearby.
GreenLinks Golf Villas at Lely Resort
Price was $705, price is now $535 per person
$535
per person
Dec 1 - Dec 5
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3-star spa aparthotel in Naples. Enjoy free parking, a full-service spa, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Flamingo Island Course - Lely Resort and Swamp Buggy Races are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was $2,216, price is now $1,070 per person
$1,070
per person
Dec 2 - Dec 9
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4.5-star luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
The Perry Hotel Naples
Save 100% on your flight
Price was $1,456, price is now $720 per person
$720
per person
Dec 2 - Dec 9
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4.5-star luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Wiggins Pass Chalet
Save 100% on your flight
Price was $932, price is now $640 per person
$640
per person
Dec 2 - Dec 9
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4-star business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular attractions Barefoot Beach and Vanderbilt Beach are located nearby.
La Quinta Inn and Suites Fort Myers I-75
Daniels Corridor
Save 100% on your flight
Price was $744, price is now $531 per person
$531
per person
Dec 6 - Dec 13
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions JetBlue Park at Fenway South and Legends Golf and Country Club are located nearby.
Sanibel Island Beach Resort
Mid Island
Save 100% on your flight
Price was $1,226, price is now $908 per person
$908
per person
Nov 28 - Dec 5
found 24 hours ago
Roundtrip non-stop flight included
Kansas City (MCI) to Fort Myers (RSW)
Stay at this 3-star beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.
Fairways Inn of Naples
Palm River Estates
Save 100% on your flight
Price was $727, price is now $545 per person
$545
per person
Dec 2 - Dec 9
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3-star hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
3-4 Night Vacations in The Estates
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in The Estates
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in The Estates
Inn on Fifth
699 5th Ave S, Naples, FL
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Hilton Marco Island Beach Resort and Spa
560 S Collier Blvd, Marco Island, FL
Stay at this 4-star beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in ...
Marco Beach Ocean Suites
480 S Collier Blvd, Marco Island, FL
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Save an average of 15% on thousands of hotels when you're signed in
Hyatt House Naples/5th Avenue
1345 5th Avenue South, Naples, FL
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S, Naples, FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
JW Marriott Marco Island Beach Resort
400 S Collier Blvd, Marco Island, FL
Stay at this 4-star beach resort in Marco Island. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff and the property ...
Bayfront Inn Fifth Avenue
1221 5th Ave S, Naples, FL
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and a marina. Our guests praise the restaurant and the bar in our reviews. ...
Naples Bay Resort & Marina
1500 Fifth Ave S, Naples, FL
Stay at this 4-star spa hotel in Naples. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Jan 21 - Wed, Jan 28
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Fri, Dec 5 - Fri, Dec 19
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Tue, Nov 11 - Tue, Nov 18
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Sun, Nov 9 - Wed, Nov 12
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
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