A bridge over calm water with boats, palm trees, and a clear sky.

Diplomat Vacations from $636

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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.
  • A waterfront hotel with multiple buildings, a dock, and a calm body of water reflecting the structures.
    Dec 19 - Dec 23

    Marriott Sanibel Harbour Resort & Spa + Flight

    Punta Rassa
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,003 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop PGD - PSM • Nonstop
    $893
    $636
    per traveler
    found 1 day ago
    Marriott Sanibel Harbour Resort & Spa
  • A golf course with a pond, sand bunkers, and lush greenery.
    Jan 10 - Jan 14

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    4 nights
    4.5 star property
    9.0/10 - Wonderful (1,001 reviews)
    "Overall, worth the stay. The place could use some updates."
    Reviewed November 5, 2026
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop PGD - PSM • Nonstop
    Save 100% on your flight
    $2,972
    $1,919
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • A pool area with lounge chairs and umbrellas, surrounded by palm trees.
    Jan 10 - Jan 14

    The Perry Hotel Naples + Flight

    Naples
    4 nights
    4.5 star property
    9.6/10 - Exceptional (1,256 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    BOS - RSW • Nonstop PGD - PSM • Nonstop
    Save 100% on your flight
    $1,494
    $979
    per traveler
    found 1 day ago
    The Perry Hotel Naples
  • A modern kitchen with white cabinetry, a built-in microwave, and a coffee maker. There is a dining area with a round table and chairs.
    Jan 14 - Jan 18

    Spacious Family Retreat Port Charlotte + Flight

    Port Charlotte
    4 nights
    2.0 star property
    10/10 - Exceptional (4 reviews)
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop RSW - BOS • 1 stop
    $2,651
    $1,820
    per traveler
    found 1 day ago
    Spacious Family Retreat Port Charlotte
  • A poolside area with a sofa, lounge chairs, a fire pit, and a view of a tropical garden.
    Jan 14 - Jan 19

    A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave + Flight

    Naples
    5 nights
    3.0 star property
    Roundtrip • Boston (BOS) - Fort Myers (RSW)
    PSM - PGD • Nonstop RSW - BOS • 1 stop
    Save 100% on your flight
    $3,197
    $2,279
    per traveler
    found 1 day ago
    A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave

Where to stay in Diplomat

Find the best Diplomat areas and neighborhoods for the activities you enjoy most.
A pier extending into the water with two gazebos at the end, under a sunset sky.

Pelican

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

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

A coastal cityscape with a beach, marina, and dense urban area.

Hancock

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

A sunset over a calm lake with a dock and palm trees.

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.

What to do near Diplomat

Fort Myers: Guided Standup Paddleboarding or Kayaking Tour

Fort Myers Dolphin & Manatee Kayak or Paddleboard Tour

$72
per adult
90% of travelers recommend
Fort Myers Dolphin & Manatee Kayak or Paddleboard Tour
See all activities near Diplomat

Diplomat Hotel Deals

A modern bathroom with a freestanding bathtub, wooden steps, and a nightstand with a lamp.

Park Motel

Park Motel
2.5 star property
Diplomat
9.2 out of 10, Wonderful, (47 reviews)
$194 nightly
The price is $216
Dec 10 - Dec 11
Total with taxes and fees
Park Motel
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.
See all properties in Diplomat
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.