Keewaydin Island Vacations from $459

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The Latest Keewaydin Island vacation packages

Price found within the past 48 hours. Click for updated prices.
The Bay Inn at Lani Kai

The Bay Inn at Lani Kai

$459
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
7.8/10 Good! (502 reviews)
the beach is very close .the room has been recently renovated

Reviewed on Sep 24, 2026

Latitude 26 Waterfront Resort & Marina

Latitude 26 Waterfront Resort & Marina

Save 100% on your flight
$581
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
8.6/10 Excellent! (1,001 reviews)
Clean room

Reviewed on Sep 22, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
$701
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing times said amenities. Prices for amenities and rentals were reasonable in my opinion. The restaurants range in price from reasonable to upscale dining. Our room was exactly as pictured. The entire property including the private beach - which was just across the road - were exceptionally clean. My only complaint was our bed was very firm for our tastes. The Gulf side beach was gorgeous. We saw many shore birds and dolphins. The bay side features a large marina and manatees in the cove. All staff we encountered were very friendly and helpful. We stayed in mid September and it appeared that most of the rooms were filled, but it was still very relaxing, quiet, and uncrowded. The location is excellent. It's easy to find off the main road through the islands and it's only a short drive to the attractions and beaches in both Sanibel and Captiva. Overall I would recommend and would stay here again.

Reviewed on Sep 20, 2026

Windward Passage Resort

Windward Passage Resort

Save 100% on your flight
$835
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
8.8/10 Excellent! (11 reviews)
Wonderful view of the ocean

Reviewed on Sep 15, 2026

The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$748
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
Espectacular hotel! Hemos estado alli en dos ocasiones y me encanta. El servicio de Ferry y Shutlle Gratuito es un plus la playa hermosa, el.paseo en manglar hermoso vimos defines, celebramos aniversario y cumpleaños de mi hija y ya quiero volver. El personal del hotel muy amable, los conductores del ferry y del bus muy buenas personas, la Vista del balcon increíble al atardecer y amanecer, la.piscima todo. Solo falta mejores desayunos y que no desmejoren la comida de la piscina.

Reviewed on Sep 24, 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
$238 nightly
$264 total
Oct 4 - Oct 5
Total with taxes and fees
9/10 Wonderful! (2,062 reviews)
"I normally don’t write reviews but I couldn’t be more impressed by this hotel. The room was very clean, well stocked, mattress was comfortable, and shower had a good water flow. Staff was very welcoming and accommodating to all are needs. The beach was clean. Just steps from the hotel. I like that ..."

Reviewed on Sep 24, 2026

Hilton Marco Island Beach Resort and Spa
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
$82 nightly
$91 total
Oct 4 - Oct 5
Total with taxes and fees
8.2/10 Very Good! (2,102 reviews)
"Perfect location, great staff, clean rooms and good breakfast"

Reviewed on Sep 24, 2026

La Quinta Inn & Suites by Wyndham Naples Downtown
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
$164 nightly
$182 total
Sep 27 - Sep 28
Total with taxes and fees
Hyatt House Naples/5th Avenue
See all 10,627 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.