Search Deals onDiplomat Vacation Packages
Diplomat Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Price was $878, price is now $594 per person
$594
per person
May 11 - May 15
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Myers (RSW)
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 in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Poolside 2BR/2.5BA Near Downtown Fort Myers
Price was $1,152, price is now $773 per person
$773
per person
May 9 - May 16
found 14 hours ago
Roundtrip flight included
Cincinnati (CVG) to Fort Myers (RSW)
Stay at this affittacamere in Fort Myers. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Broadway Palm Dinner Theatre and Vietnam War Memorial are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was $3,288, price is now $1,575 per person
$1,575
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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 $1,302, price is now $794 per person
$794
per person
May 9 - May 16
found 19 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 $1,325, price is now $851 per person
$851
per person
May 11 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this condo 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.
Edison Beach House
Price was $975, price is now $654 per person
$654
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Matanzas Inn Bayside Resort and Marina
Price was $1,003, price is now $677 per person
$677
per person
May 21 - May 25
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 daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,038, price is now $702 per person
$702
per person
Jun 3 - Jun 7
found 12 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public 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 ...
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
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property ...
Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park
10150 Daniels Pkwy 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 breakfast and the clean rooms ...
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.
Sun, Apr 19 - Thu, Apr 23
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$91 Roundtrip, found 1 hour ago
$91
Roundtrip
found 1 hour ago
Mon, May 4 - Fri, May 22
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$119 Roundtrip, found 1 hour ago
$119
Roundtrip
found 1 hour ago
Tue, Apr 28 - Wed, May 13
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$182 Roundtrip, just found
$182
Roundtrip
just found
Sat, Apr 25 - Wed, May 13
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$192 Roundtrip, found 5 hours ago
$192
Roundtrip
found 5 hours ago
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