Search Deals onDiplomat Vacation Packages
Diplomat Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
Save 100% on your flight
Price was $922, price is now $596 per person
$596
per person
May 29 - Jun 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Chadwick Cove Resort & Marina
Price was $904, price is now $664 per person
$664
per person
May 27 - May 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Englewood. Enjoy free WiFi, free parking, and 7 restaurants. Popular attractions Englewood Beach and Lemon Bay are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $2,013, price is now $1,106 per person
$1,106
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,105, price is now $667 per person
$667
per person
Jun 13 - Jun 19
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Save 100% on your flight
Price was $1,266, price is now $823 per person
$823
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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.
Mariners Boathouse by Coolvacay
South Island
Save 100% on your flight
Price was $1,040, price is now $707 per person
$707
per person
May 28 - Jun 2
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo 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.
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,313, price is now $946 per person
$946
per person
May 29 - Jun 3
found 19 hours ago
Roundtrip flight included
Boston (BOS) 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 North Captiva Island Beach and Captiva Beach are located nearby.
Shell Island Beach Club
East End
Price was $2,303, price is now $1,668 per person
$1,668
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Sanibel Island Lighthouse 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 18 - Mon, Jun 1
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Tue, May 19 - Thu, May 21
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Sun, May 3 - Thu, May 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$170 Roundtrip, found 3 days ago
$170
Roundtrip
found 3 days ago
Tue, May 12 - Wed, May 20
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
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- Estero Boulevard Beach Vacations
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- Sanibel Island Lighthouse Vacations
- Captiva Beach Vacations
- Sanibel Harbour Beach Vacations