Keewaydin Island Vacations from $470

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The Latest Keewaydin Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Latitude 26 Waterfront Resort & Marina

Latitude 26 Waterfront Resort & Marina

Save 100% on your flight
$470
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,006 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$764
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,048 reviews)
For 2 of my 4 day work travel I had to work from the room and there was a dog barking for 3 hrs straight. When I went to check the room number to tell the front desk, it turned out the roof was for STAFF personel!! There was no welcome card explaining how to get on the WiFi, when food was available, since there's no room service. Hours for amenities. Room key stopped working twice 2 days in a row when I got back late from working.

Reviewed on Aug 29, 2026

The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

Save 100% on your flight
$551
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,771 reviews)
Great location for Fort Meyers beach. Our room was dated/worn and not particularly clean (bedsheets stained etc). That being said, our room was old in the older part of the resort, so the newer side may be better? On site bar is worth a visit for food/drink

Reviewed on Aug 27, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
$894
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
No problems

Reviewed on Aug 29, 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

Save 100% on your flight
$611
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
Very good condition, very comfy and practical

Reviewed on Aug 28, 2026

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What to do in Keewaydin Island

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

$67
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

$73
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

$78
per adult
Naples: Sightseeing and Dining Cruises
See all activities in Keewaydin Island

Keewaydin Island Hotel Deals

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
$226 nightly
$251 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (1,993 reviews)
"Clean room beach view, parking is an extra charge."

Reviewed on Aug 30, 2026

Hilton Marco Island Beach Resort and Spa
The Perry Hotel Naples

The Perry Hotel Naples

12155 Tamiami Trail N Naples FL
Fully refundableReserve now, pay when you stay
$129 nightly
$143 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (1,092 reviews)
"For 2 of my 4 day work travel I had to work from the room and there was a dog barking for 3 hrs straight. When I went to check the room number to tell the front desk, it turned out the roof was for STAFF personel!! There was no welcome card explaining how to get on the WiFi, when food was available, ..."

Reviewed on Aug 29, 2026

The Perry Hotel Naples
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

1555 5th Ave S Naples FL
Fully refundableReserve now, pay when you stay
$68 nightly
$75 total
Sep 20 - Sep 21
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Naples Downtown
See all 10,617 properties in Keewaydin Island
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.

Find the Best Keewaydin Island Vacation Packages

Things to do near Keewaydin Island

Keewaydin Island offers a perfect escape for beach lovers and adventure seekers alike. Visitors can enjoy a variety of activities such as beach excursions, wildlife tours, and the exciting Keewaydin Tiki Boat Island Adventure. With its beautiful recreational areas and centers, the island is ideal for day trips and relaxing beach vacations, ensuring a memorable outdoor experience for everyone.

Shopping

For a great shopping experience near Keewaydin Island, visit Tin City, just 5 miles away, offering entertainment and family vibes. The Naples Outlet Center, 6 miles away, features various shops and dining. Lastly, explore Village on Venetian Bay, 9 miles away, known for its charming atmosphere and unique finds.

Recreation

Relax at East Naples Community Park, where you can enjoy serene walking trails and tranquil picnic areas. For sports enthusiasts, TPC Treviso Bay offers a stunning golf experience surrounded by nature. Alternatively, indulge in luxury at Mustang Course - Lely Resort, a private club perfect for unwinding in style.

Adventure

Experience the thrill of the ocean at Sanibel Sea School, located 30 miles from Keewaydin Island, where you can explore underwater sports. For family fun, visit Beach Bowl, also 30 miles away, featuring arcade adventures. Don’t miss Marco Island Ski & Watersports, just 10 miles away, offering exciting water sports.

Nightlife

Keewaydin Island offers a laid-back nightlife with beach bonfires and sunset views. Enjoy cocktails at local beach bars, or join a sunset cruise for stunning vistas. For a relaxed vibe, gather around fire pits under the stars and soak in the island's tranquil charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Keewaydin Island

Keewaydin Island, Florida, is a paradise for beach lovers and outdoor adventurers. This idyllic destination offers pristine beaches, scenic marinas, and vibrant local culture. Visitors can explore various attractions, enjoy island vacation packages, and take in the diverse wildlife. Whether you're seeking relaxation or adventure, Keewaydin Island provides an unforgettable experience with its beautiful amenities and outdoor activities, making it a perfect spot for your next getaway.

  • Naples Beach: Located 4 miles from Keewaydin Island, Naples Beach offers a pristine stretch of white sand and warm Gulf waters. The beach vibe is perfect for relaxation, sunbathing, and enjoying water activities like swimming and paddleboarding. The stunning sunsets here are a must-see.
  • Fifth Avenue South: About 5 miles away, Fifth Avenue South is the heart of Naples’ city life, lined with upscale shops, art galleries, and gourmet restaurants. This vibrant street atmosphere is perfect for strolling, dining, and indulging in local culture.
  • Naples Pier: Situated 4 miles from Keewaydin Island, Naples Pier is ideal for fishing, dolphin watching, or simply enjoying the scenic views. The pier's excursions vibe invites visitors to take leisurely walks and soak in the ocean breeze.

Best time to go to Keewaydin Island

The best time to visit Keewaydin Island, Naples is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January65.7°F (18.7°C)No RainMostly SunnyAverageAverage
February68.2°F (20.1°C)No RainSunnyAverageSlightly High
March70.3°F (21.3°C)No RainSunnySlightly HighSlightly High
April75.4°F (24.1°C)No RainSunnySlightly HighSlightly High
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnySlightly HighAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnySlightly LowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnySlightly LowSlightly Low
November73.0°F (22.8°C)No RainMostly SunnySlightly LowAverage
December69.3°F (20.7°C)No RainMostly SunnyAverageAverage

Tips to save on your trip to Keewaydin Island

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically August to October) for more affordable package holidays to Keewaydin Island.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Keewaydin Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Southwest Florida Intl. Airport (RSW)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.