Diplomat Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Diplomat Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
Price was $1,092, price is now $697 per person
$697
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Fort Myers (RSW)
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 helpful staff in our reviews. Popular attractions Edison Mall and Calusa Nature Center and Planetarium are located nearby.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $1,489, price is now $817 per person
$817
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Fort Myers (RSW)
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 reviews. Popular attractions Edison Mall and Barbara B Mann Hall are located nearby.
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $2,101, price is now $1,261 per person
$1,261
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Captiva Beach and Captiva Chapel By the Sea are located nearby.
South Seas Resort
Save 100% on your flight
Price was $2,780, price is now $1,699 per person
$1,699
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy 3 outdoor pools, 7 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina are located nearby.
Edison Beach House
Save 100% on your flight
Price was $2,164, price is now $1,453 per person
$1,453
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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 Times Square are located nearby.
Lani Kai Beachfront Resort
Save 100% on your flight
Price was $1,940, price is now $1,316 per person
$1,316
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent Beach Family Park are located nearby.
Top Hotel Deals
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
31.87 km from Diplomat
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 ...
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
27.38 km from Diplomat
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent ...
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
24.57 km from Diplomat
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 ...
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
27.3 km from Diplomat
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 ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
15.02 km from Diplomat
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 ...
Sanibel Island Beach Resort
1231 Middle Gulf Dr Sanibel FL
31.44 km from Diplomat
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. ...
DiamondHead Beach Resort
2000 Estero Blvd Fort Myers Beach FL
27.45 km from Diplomat
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG
3427 Forum Blvd Fort Myers FL
15.59 km from Diplomat
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 in our reviews. ...
Hyatt Place Fort Myers/at The Forum
2600 Champion Ring Rd Fort Myers FL
14.03 km from Diplomat
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 helpful ...
Hilton Garden Inn Ft Myers
12600 University Dr Fort Myers FL
15.8 km from Diplomat
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 ...
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
26.45 km from Diplomat
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 ...
Sundial Beach Resort & Spa
1451 Middle Gulf Drive Sanibel FL
32.02 km from Diplomat
Book a stay at this luxury condo in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the property condition in our reviews. Popular ...
Doubletree by Hilton Fort Myers at Bell Tower Shops
13051 Bell Tower Drive Fort Myers FL
16.99 km from Diplomat
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 and ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Feb 23 - Wed, Feb 25
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$88 Roundtrip, found 15 hours ago
$88
Roundtrip
found 15 hours ago
Tue, Mar 3 - Thu, Mar 12
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$96 Roundtrip, found 15 hours ago
$96
Roundtrip
found 15 hours ago
Sun, Jan 18 - Thu, Jan 22
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Wed, Feb 18 - Wed, Feb 25
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Thu, Feb 5 - Mon, Feb 23
YYZ
Pearson Intl.
RSW
Southwest Florida Intl.
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago