Diplomat Vacations from $723

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Your Diplomat Vacation

Booking a Diplomat vacation package is an ideal way to become familiar with this neighborhood. From its renowned sites to its lesser-known delights, there's plenty to discover. Your trip to Diplomat wouldn't be complete without seeing top attractions nearby such as Pine Island Shopping Center, Del Tura Golf and Country Club and Shell Factory and Nature Park. Whatever your ideal Diplomat vacation may look like, you can turn it into reality with Expedia.

The Latest Diplomat Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $1,305, price is now $723 per person
$723
per person
Feb 27 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Staff was fantastic. Room was nice and overall great experience.

Reviewed on Dec 7, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,476, price is now $824 per person
$824
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
We especially loved the kayaking

Reviewed on Dec 7, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $2,582, price is now $1,443 per person
$1,443
per person
Feb 27 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Room was amazing! View spectacular! Service the best!

Reviewed on Dec 7, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $3,724, price is now $2,223 per person
$2,223
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,000 reviews)
The bathtub was blacked and sink was leaking water ……. Missing my art knife after room cleaned

Reviewed on Nov 29, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,557, price is now $945 per person
$945
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
Nice, spacious rooms. Good bar and restaurant. Great gym. Also, no children!

Reviewed on Dec 4, 2025

Where to stay in Diplomat

Find the best Diplomat areas and neighborhoods for the activities you enjoy most. Learn more about Diplomat
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Pelican

1 out of top 10 points of interest in this area
4.5/5(46 area reviews)

If you're spending some time in Pelican, Tarpon Point and Harbour View Gallery are top sights worth seeing.

Find hotels in Pelican

Diplomat Hotel Deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $204 total per night from Jan 2 to Jan 3
$204 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,650 reviews)
Yes

Reviewed on Dec 2, 2025

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
$212 nightly
The price is $237 total per night from Dec 14 to Dec 15
$237 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,685 reviews)
Great place. Great entertainment

Reviewed on Dec 2, 2025

Margaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $172 total per night from Dec 9 to Dec 10
$172 total
Dec 9 - Dec 10
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Clean rooms, friendly staff, so much to do there and nearby

Reviewed on Dec 3, 2025

Lani Kai Beachfront Resort
See all 15,693 properties in Diplomat
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Diplomat

Veterans park

Four Mile Cove Ecological Preserve

Enjoy the beautiful sunsets and explore Four Mile Cove Ecological Preserve, a lovely green space in Cape Coral. Amble around this family-friendly area's beautiful beaches or attend a baseball game.

Four Mile Cove Ecological Preserve

Shell Factory and Nature Park

Explore the great outdoors at Shell Factory and Nature Park, a lovely green space in North Fort Myers. Attend a sporting event in this family-friendly area.

Shell Factory and Nature Park

Cape Coral Yacht Club Beach

Why not spend a lazy afternoon at Cape Coral Yacht Club Beach during your trip to Cape Coral?

Cape Coral Yacht Club Beach

Things to do

Marco Island: 10,000 Islands Shelling Boat Tour

Marco Island: 10,000 Islands Shelling Boat Tour

$100
per adult
100% of travellers recommend
Marco Island: 10,000 Islands Shelling Boat Tour
Historic Walking Tour of Fort Myers

Historic Walking Tour of Fort Myers

$26
per adult
100% of travellers recommend
Historic Walking Tour of Fort Myers
Fort Myers: Guided Kayaking Eco Tour in Pelican Bay

Fort Myers: Guided Kayaking Eco Tour in Pelican Bay

$75
per adult
Fort Myers: Guided Kayaking Eco Tour in Pelican Bay
See all activities in Cape Coral
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.