Keewaydin Island Vacation Packages 2025/2026 from $256

The Latest Keewaydin Island vacation packages

Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Ft Myers

Villas

Save 100% on your flight

$244

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,011 reviews)

The man that was working the night we checked in is very rude. We had two interactions with him and both were awful.

Reviewed on Oct 2, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

$905

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.8/10 Excellent! (1,002 reviews)

Our experience at La Playa was exceptional, everything was what we wanted and expected it to be

Reviewed on Sep 29, 2025

South Seas Resort

Save 100% on your flight

$985

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.4/10 Very Good! (1,003 reviews)

First visit to South Seas. It is at the far northern part of Captiva Island. Its secluded, and quiet. The rooms are actually condo's which are really nice, clean and comfortable. Please keep in mind this resort is still undergoing construction from Hurricane Ian, but they have done a great job and can't wait for it to be finished as it will be amazing. The beach is gorgeous, not crowded and the chairs and umbrellas on the beach are a great touch as we forgot to bring ours. Every employee we met was so friendly, helpful and kind. Strongly recommend renting a golf cart. It helps get around the resort which is quite large and bonus it allows you to go into the little town which is adorable and has additional dining options. Very nice having a Starbucks on property as well. We will be visiting again. If you are looking for a quiet trip with rest and relaxation and great accommodations this is the place!!

Reviewed on Oct 5, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$506

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (639 reviews)

Excellent service at the pool area

Reviewed on Oct 5, 2025

Hyatt Place Fort Myers/at The Forum

The Forum

Save 100% on your flight

$426

per person

Dec 14 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.2/10 Very Good! (1,004 reviews)

Friendly helpful and professional staff

Reviewed on Oct 6, 2025

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Discover the most popular places to visit in Keewaydin Island

Naples Beach

4.5/5(1,407 reviews)

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

4.5/5(45 reviews)

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Naples Pier

4.5/5(1,161 reviews)

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

What to do in Keewaydin Island

Best of Marco Dolphin Tour

$100

per adult

Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

$127

per adult

Everglades National Park: 2 hour Dolphin & Birding Boat Tour

Everglades: 2 hour Manatee, Dolphin & Birding Boat Tour

$110

per adult

See all activities in Keewaydin Island

Keewaydin Island Hotel Deals

Naples Grande Beach Resort

475 Seagate Drive, Naples, FL

Fully refundable

$245 nightly

$272 total

Oct 13 - Oct 14

Total with taxes and fees

9/10 Wonderful! (1,841 reviews)

"Amazing place to rest and kids to have fun"

Reviewed on Oct 7, 2025

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd, Marco Island, FL

Fully refundableReserve now, pay when you stay

$252 nightly

$280 total

Oct 29 - Oct 30

Total with taxes and fees

8.8/10 Excellent! (1,592 reviews)

"The beach is beautiful and the staff will set you up with lounge chairs and an umbrella. The short walk to the beach is enjoyable with lush tropical plants along the walkway and then opening up to a beautiful gulf beach. The pool and spa area are very nice with the wonderful staff serving food and ..."

Reviewed on Oct 4, 2025

Marco Beach Ocean Suites

480 S Collier Blvd, Marco Island, FL

$168 nightly

$186 total

Nov 4 - Nov 5

Total with taxes and fees

8.8/10 Excellent! (966 reviews)

"Very well located. Amazing beach at the hotel. Lots of restaurants near."

Reviewed on Oct 7, 2025

See all 10,542 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.