Search Deals onDiplomat Vacation Packages
Diplomat Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Best Western Naples Inn & Suites
Moorings
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
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 pool in our reviews. Popular attractions Naples Zoo at Caribbean Gardens and Fifth Avenue South are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Bellasera Resort
Old Naples
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this business-friendly condo in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
Inn on Fifth
Old Naples
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
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. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
The Perry Hotel Naples
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Tollgate Inn
Rural Estates
Save 100% on your flight
per person
Aug 12 - Aug 18
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Paradise Coast Sports Compex and Swamp Buggy Races are located nearby.
GreenLinks Golf Villas at Lely Resort
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
The Vistas At Eastwood Apartments By Barsala
Eastwood Village
Save 100% on your flight
per person
Aug 25 - Aug 31
found 24 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Fort Myers (RSW)
Stay at this 4-star aparthotel in Fort Myers. Enjoy free WiFi, a fitness center, and in-room washers/dryers. Popular attractions Edison Mall and Calusa Nature Center and Planetarium are located nearby.
3-4 Night Vacations in Diplomat
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Diplomat
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Diplomat
Vantage Apartments by Barsala
3050 Steeple Circle, North Fort Myers, FL
Stay at this 3.5-star aparthotel in North Fort Myers. Enjoy free WiFi, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Edison Mall and ...
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Times Square ...
Sunseeker Resort Charlotte Harbor
5500 Sunseeker Way, 785, Punta Gorda, FL
Stay at this 4.5-star luxury resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful ...
Save an average of 15% on thousands of hotels when you're signed in
Sanibel Island Beach Resort
1231 Middle Gulf Dr, Sanibel, FL
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. ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E, Cape Coral, FL
Book a stay at this business-friendly hotel in Cape Coral. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
Stay at this 4-star beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
The Lighthouse Resort Inn & Suites
1051 5th St, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular ...
Hilton Garden Inn Ft Myers
12600 University Dr, Fort Myers, FL
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
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.
Mon, Sep 15 - Fri, Sep 26
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$68 Roundtrip, found 20 hours ago
$68
Roundtrip
found 20 hours ago
Thu, Sep 4 - Sun, Sep 7
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
Mon, Sep 22 - Sun, Sep 28
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$110 Roundtrip, found 3 days ago
$110
Roundtrip
found 3 days ago
Wed, Oct 29 - Tue, Nov 4
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
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