Diplomat Vacation Packages 2026 from $736

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.

Casa Tiki

Hancock

Save 100% on your flight

$736

per person

Oct 31 - Nov 7

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

No reviews

The Perry Hotel Naples

Save 100% on your flight

$810

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

amazing hotel, excellent loction, close to vanderbilt beach

Reviewed on Aug 21, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$1,060

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Casa Ybel Resort

Mid Island

Save 100% on your flight

$784

per person

Oct 30 - Nov 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (397 reviews)

Marriott Sanibel Harbour Resort & Spa

Punta Rassa

Save 100% on your flight

$1,025

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,012 reviews)

Where to stay in Diplomat

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

A pier extending into the water with two gazebos at the end, under a sunset sky.

Pelican

1 out of top 10 points of interest in this area

If you're spending some time in Pelican, Tarpon Point and Chabad Jewish Center are top sights worth seeing.

A coastal residential area with a marina, dense greenery, and high-rise buildings in the background.

Caloosahatchee

3 out of top 10 points of interest in this area

If you're spending some time in Caloosahatchee, Cape Coral Yacht Club Beach and Dolphin Marina are top sights worth seeing.

A beach with a sunset, a colorful umbrella, and a surfboard.

Hancock

4 out of top 10 points of interest in this area

While visiting Hancock, you might make a stop by sights like Four Mile Cove Ecological Preserve and Pine Island Shopping Center.

A waterfront with colorful houses and a dock.

Yacht Club

While there might not be top attractions in Yacht Club, you can explore the larger area and discover places like Cape Coral Yacht Club Beach and Dolphin Marina.

A wooden pier extending into calm water with a clear sky and distant land.

Burnt Store

Though Burnt Store might not have many top sights, you can venture to the surrounding area to see attractions like Coral Oaks Golf Course and Burnt Store Marina.

Diplomat Hotel Deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Fully refundableReserve now, pay when you stay

$198 nightly

$221 total

Aug 28 - Aug 29

Total with taxes and fees

9.2/10 Wonderful! (3,234 reviews)

"Espectacular increíble es un 1000 de 10"

Reviewed on Aug 20, 2026

Baymont by Wyndham Fort Myers Central

4850 S Cleveland Ave Fort Myers FL

Fully refundableReserve now, pay when you stay

$62 nightly

$69 total

Sep 1 - Sep 2

Total with taxes and fees

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$212 nightly

$237 total

Aug 31 - Sep 1

Total with taxes and fees

See all 16,239 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.