Search Deals onDiplomat Vacation Packages
Diplomat Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Lighthouse Resort Inn & Suites
Save 100% on your flight
Price was $670, price is now $471 per person
$471
per person
May 31 - Jun 4
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,748, price is now $1,721 per person
$1,721
per person
May 29 - Jun 5
found 14 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this 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 $1,272, price is now $805 per person
$805
per person
May 29 - Jun 5
found 14 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Save 100% on your flight
Price was $1,288, price is now $836 per person
$836
per person
Jun 13 - Jun 20
found 11 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this aparthotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
Manasota Key Resort
Save 100% on your flight
Price was $2,160, price is now $1,486 per person
$1,486
per person
Jun 13 - Jun 20
found 11 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this beach hotel in Englewood. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Englewood Beach and Stump Pass Beach State Park are located nearby.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton
Save 100% on your flight
Price was $1,602, price is now $1,132 per person
$1,132
per person
Jun 13 - Jun 20
found 11 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this hotel in Punta Gorda. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
THE Palmview AND Sandpiper Inns
Mid Island
Save 100% on your flight
Price was $759, price is now $545 per person
$545
per person
May 31 - Jun 4
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this motel in Sanibel. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.
Casa Playa Beach Resort
Save 100% on your flight
Price was $905, price is now $650 per person
$650
per person
May 31 - Jun 4
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach 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
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff ...
Baymont by Wyndham Fort Myers Central
4850 S Cleveland Ave Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Book a stay at this 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 ...
Sanibel Island Beach Resort
1231 Middle Gulf Dr Sanibel FL
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Estero Boulevard ...
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
Hilton Garden Inn Ft Myers
12600 University Dr Fort Myers FL
Book a stay at this 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, May 4 - Fri, May 22
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$108 Roundtrip, found 4 days ago
$108
Roundtrip
found 4 days ago
Tue, Jun 23 - Thu, Jul 9
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$140 Roundtrip, found 3 hours ago
$140
Roundtrip
found 3 hours ago
Sun, May 3 - Sat, May 9
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$184 Roundtrip, found 2 hours ago
$184
Roundtrip
found 2 hours ago
Fri, May 15 - Wed, May 20
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$202 Roundtrip, found 12 hours ago
$202
Roundtrip
found 12 hours ago
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