Keewaydin Island Vacation Rentals from $169: Search Short-Term Rentals

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Our top choices for Keewaydin Island vacation rentals

A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

1. Bellasera Resort

Downtown

vasilisa

$361 nightly

Nov 15 - Nov 16

Total with taxes and fees

An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

2. Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

Old Naples

Robert W.

$545 nightly

Nov 14 - Nov 15

Total with taxes and fees

A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

3. Noel Real Estate

East Naples

Lauren

$361 nightly

Nov 22 - Nov 23

Total with taxes and fees

An indoor pool area with a glass floor, seating around the pool, and a bar area with a blue ceiling and hanging lights.

4. Park Shore Resort

Park Shore

nathaly

$349 nightly

Dec 5 - Dec 6

Total with taxes and fees

A white pergola with a brick pathway leading to a house.

5. Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.

Old Naples

Andrew R.

$577 nightly

Nov 30 - Dec 1

Total with taxes and fees

A beach with a long pier extending into the ocean, surrounded by palm trees and a well-maintained lawn.

6. 1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt

Old Naples

Dallas M.

$640 nightly

Dec 1 - Dec 2

Total with taxes and fees

A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

7. Free Golf Until Oct! Naples Condo w/ Resort Pool

Naples

Mark

$361 nightly

Nov 15 - Nov 16

Total with taxes and fees

A white house with a metal roof, surrounded by a well-maintained lawn and a gravel path leading to a seating area with white chairs.

8. c.1930's Cottage in picturesque setting, 2 blocks to Gulf and 5th Ave S.

Old Naples

terry s.

$698 nightly

Nov 14 - Nov 15

Total with taxes and fees

An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

9. Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

East Naples

Andrew F.

$299 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern kitchen with a central island, wooden stools, and a sliding glass door leading to a patio.

10. `The Boho Bliss` - Reset & Recharge Wellness House

East Naples

Nancy S.

$353 nightly

Dec 2 - Dec 3

Total with taxes and fees

A swimming pool with clear water, surrounded by palm trees and lounge chairs.

11. Holidays in paradise at the Lely Resort

Naples

Adam Y.

$286 nightly

Nov 18 - Nov 19

Total with taxes and fees

A covered outdoor deck with lounge chairs, a hot tub, and a view of a garden and buildings.

12. Green Turtle Boathouse/HOT TUB view of the canal

East Naples

Heidi

$437 nightly

Nov 15 - Nov 16

Total with taxes and fees

A covered porch with a wooden ceiling, string lights, a ceiling fan, wicker furniture, and a view of greenery outside.

13. Cypress Cove

Naples

Rebecca L.

$381 nightly

Nov 15 - Nov 16

Total with taxes and fees

A cozy living room with a grey sofa, a small table, and chairs. There is a window with curtains, a lamp, and a mirror on the wall.

14. King Bed Near Pickleball, Beach & Downtown

East Naples

Francois S.

$208 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

15. `The Coastal Dream` only 3miles to the beach.

East Naples

Jesse L.

$291 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with a dining area, large windows, and a view of an outdoor swimming pool.

16. THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches

East Naples

Robert K.

$581 nightly

Nov 21 - Nov 22

Total with taxes and fees

A modern kitchen with a central island, a dining area, and a large sliding glass door leading to an outdoor patio.

17. ` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

East Naples

Anonymous traveler

$364 nightly

Nov 25 - Nov 26

Total with taxes and fees

A pier extending into a clear blue sea with a sandy beach at the end.

18. 3BR Golf & Lake View Villa • Pool • Lely Resort

Naples

Thomas H.

$375 nightly

Nov 17 - Nov 18

Total with taxes and fees

19. Free Golf Until Oct! Naples Condo w/ Resort Pool

Naples

Colleen V.

$349 nightly

Nov 15 - Nov 16

Total with taxes and fees

A white pergola with climbing plants and pink flowers.

20. Romantic Cottage - With a king, 2 Blocks to Gulf, Old Naples with lit sidewalks.

Old Naples

Lynda D.

$776 nightly

Nov 14 - Nov 15

Total with taxes and fees

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Top Keewaydin Island Hotel Reviews

Fairways Inn of Naples

10/10 Excellent

"Exceptional !!"

Great Wolf Lodge Naples

8/10 Good

"It was very nice, especially on Friday when it was not packed and we didn’t have to wait long lines. My only issue was that Hotels.com charged me additional of $80 for an extra guest which we didn’t have as it was only me and my two girls. and when I called Hotels.com, they said to contact the hotel so they’ll email them a confirmation that it was only me with two kids… which I did. the hotel said they can’t help me with that that I should contact Hotels.com. Hotels.com said I should contact the hotel directly… just playing ping-pong. Nobody helped and I still pay the $80 additional for nothing. Also, when I left the hotel, I got a receipt that I paid for a total of two nights parking and breakfast that I took my kids on Saturday morning. ( which was not great at all for the $70. I paid… there’s Dunkin’ Donuts in the hotel that was better for us) A few days later I saw that I was charged $68.27 directly from my credit card… I called the hotel to find out what’s the charge for they said I did not return the towels which obviously I did… I really don’t need towels with blue stripes from a hotel…. Long story short I received credit for that made me feel that they’re trying to charge the additional and if you’re lucky enough to notice you did than if not, you lose. Basically, I’m sure I’m gonna come back to the hotel"

Trianon Bonita Bay

10/10 Excellent

"We love this hotel! It’s in a great location with plenty to do nearby. Our room was lovely, and the lake view was such a nice surprise. The staff were friendly and helpful, as always. The only small hiccup was the hot tub. The water was hot, but the jets weren’t working. We still had a wonderful stay. This was our third time here, and we’ll definitely be back!"

LaPlaya Beach & Golf Resort - A Noble House Resort

8/10 Good

"Great resort. Probably the nicest on the entire run of resorts on this beach. And that includes the Ritz-Carlton just upo the way. Obviously, the Ritz is classier, but La Playa felt more exclusive and comfortable. The beach experience is top-notch, with complimentary umbrellas and beach chairs upon request. The bar and restaurant were very good. Drinks are pricey, to be sure, which can add up if you're ordering while relaxing on the beach for days on end. About a 25 minute drive to the best restaurants and shops in Old Town Naples. This was a little far for us, since we didn't have a car and Uber'd whenever we went out. Overall, a very nice experience."

Find out more about Keewaydin Island

Everything you need to know about Keewaydin Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Keewaydin Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Keewaydin Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Keewaydin Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Keewaydin Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Keewaydin Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $169 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Keewaydin Island rentals

At Expedia, we put the best Keewaydin Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Keewaydin Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Keewaydin Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Keewaydin Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Keewaydin Island vacation rentals

1. Bellasera Resort

2. Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

3. Noel Real Estate

4. Park Shore Resort

5. Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.

6. 1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt

7. Free Golf Until Oct! Naples Condo w/ Resort Pool

8. c.1930's Cottage in picturesque setting, 2 blocks to Gulf and 5th Ave S.

9. Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

10. `The Boho Bliss` - Reset & Recharge Wellness House

11. Holidays in paradise at the Lely Resort

12. Green Turtle Boathouse/HOT TUB view of the canal

13. Cypress Cove

14. King Bed Near Pickleball, Beach & Downtown

15. `The Coastal Dream` only 3miles to the beach.

16. THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches

17. ` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

18. 3BR Golf & Lake View Villa • Pool • Lely Resort

19. Free Golf Until Oct! Naples Condo w/ Resort Pool

20. Romantic Cottage - With a king, 2 Blocks to Gulf, Old Naples with lit sidewalks.

Find vacation rentals that suit your style

Top Keewaydin Island Hotel Reviews

Fairways Inn of Naples

Hilton Naples

Great Wolf Lodge Naples

Hilton Marco Island Beach Resort and Spa

Marco Island Lakeside Inn

Trianon Bonita Bay

LaPlaya Beach & Golf Resort - A Noble House Resort

Find out more about Keewaydin Island

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