A coastal landscape with a sandy beach, clear turquoise waters, and a network of small islands.

Keewaydin Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Keewaydin Island vacation rentals

A spacious, multi-level hotel lobby with a grand chandelier, a staircase, and a view of the outdoors.

1. Bellasera Resort

Bellasera Resort
4.0 star property
Downtown
9.6 out of 10, Exceptional, (2,346 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
$357 nightly
The price is $396
Nov 15 - Nov 16
Total with taxes and fees
Bellasera Resort
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!

Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
Old Naples
10.0 out of 10, Exceptional, (45 reviews)
"Easy parking and check inGreat communication Great location to beach and restaurantsBeautifully appointed Recommend highly for an easy relaxing Naples stay"
United States
Robert W.
$567 nightly
The price is $625
Nov 15 - Nov 16
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

3. Noel Real Estate

Noel Real Estate
2.0 star property
East Naples
9.0 out of 10, Wonderful, (4 reviews)
"Property was easy to find and just as described and listed. very home-feeling and comfortable. "
United States
Lauren
$361 nightly
The price is $400
Nov 23 - Nov 24
Total with taxes and fees
Noel Real Estate
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 Resort
3.0 star property
Park Shore
8.8 out of 10, Excellent, (733 reviews)
"I have been going there for over 30 years, and park shore never disappoints. We love the atmosphere and the tranquility."
United States
nathaly
$349 nightly
The price is $387
Dec 5 - Dec 6
Total with taxes and fees
Park Shore Resort
A sunset over a calm sea with boats and a sandy beach.

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

Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.
Old Naples
9.8 out of 10, Exceptional, (40 reviews)
"Enjoyed our stay. Clean, stylish, conveniently located to the beach, stores and restaurants. "
United States
Andrew R.
$570 nightly
The price is $628
Nov 30 - Dec 1
Total with taxes and fees
Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.
An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

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

1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
Old Naples
9.8 out of 10, Exceptional, (212 reviews)
"Amazing location! Beach is right there, shops, restaurants, coffee shops! Had a wonderful time! Comfortable condo! Very nice hosts!"
United States
Dallas M.
$640 nightly
The price is $705
Dec 1 - Dec 2
Total with taxes and fees
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
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

Free Golf Until Oct! Naples Condo w/ Resort Pool
3.5 star property
Naples
10.0 out of 10, Exceptional, (1 review)
"We spent a weekend here while visiting family in the area. Great location for us. Super friendly and helpful. Nice sunset view over the golf course. "
United States
Mark
$361 nightly
The price is $401
Nov 15 - Nov 16
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
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.

c.1930's Cottage in picturesque setting, 2 blocks to Gulf and 5th Ave S.
Old Naples
10.0 out of 10, Exceptional, (22 reviews)
"This place had everything we needed with a great location , "
United States
terry s.
$726 nightly
The price is $800
Nov 15 - Nov 16
Total with taxes and fees
c.1930's Cottage in picturesque setting, 2 blocks to Gulf and 5th Ave S.
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

Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
East Naples
9.2 out of 10, Wonderful, (56 reviews)
"We had a great visit. Quiet and well kept."
United States
Andrew F.
$299 nightly
The price is $329
Nov 22 - Nov 23
Total with taxes and fees
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A cozy outdoor seating area with wooden chairs and a central fire feature, surrounded by lush greenery and string lights.

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

`The Boho Bliss` - Reset & Recharge Wellness House
East Naples
10.0 out of 10, Exceptional, (5 reviews)
"Great property, clean, quiet, snd convenient. Would definitely stay again."
United States
Nancy S.
$353 nightly
The price is $371
Dec 2 - Dec 3
Total with taxes and fees
`The Boho Bliss` - Reset & Recharge Wellness House
A swimming pool with a stone waterfall feature, surrounded by palm trees and lounge chairs.

11. Holidays in paradise at the Lely Resort

Holidays in paradise at the Lely Resort
Naples
10.0 out of 10, Exceptional, (62 reviews)
"Very nice stay!"
United States
Adam Y.
$286 nightly
The price is $314
Nov 18 - Nov 19
Total with taxes and fees
Holidays in paradise at the Lely Resort
A wooden table with a bottle and two glasses, set on a deck with lounge chairs.

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

Green Turtle Boathouse/HOT TUB view of the canal
East Naples
8.0 out of 10, Very good, (1 review)
"Nice and clean. Quiet neighborhood."
United States
Heidi
$437 nightly
The price is $482
Nov 15 - Nov 16
Total with taxes and fees
Green Turtle Boathouse/HOT TUB view of the canal
A covered porch with a wooden ceiling, string lights, a ceiling fan, wicker furniture, and a view of greenery outside.

13. Cypress Cove

Cypress Cove
Naples
10.0 out of 10, Exceptional, (16 reviews)
"This was a wonderful place to stay, clean, spacious with a beautiful yard!"
United States
Rebecca L.
$350 nightly
The price is $386
Nov 16 - Nov 17
Total with taxes and fees
Cypress Cove
An outdoor patio with a bar area, surrounded by bamboo trees and a white building in the background.

14. King Bed Near Pickleball, Beach & Downtown

King Bed Near Pickleball, Beach & Downtown
East Naples
9.8 out of 10, Exceptional, (8 reviews)
"Good communication Decent location Accurate listing"
United States
Francois S.
$203 nightly
The price is $223
Nov 17 - Nov 18
Total with taxes and fees
King Bed Near Pickleball, Beach & Downtown
A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

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

`The Coastal Dream` only 3miles to the beach.
East Naples
9.8 out of 10, Exceptional, (26 reviews)
"Great location, everything was perfect!"
United States
Jesse L.
$291 nightly
The price is $302
Nov 15 - Nov 16
Total with taxes and fees
`The Coastal Dream` only 3miles to the beach.
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

THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches
East Naples
10.0 out of 10, Exceptional, (37 reviews)
"Great Home and Host. Close to many attractions."
United States
Robert K.
$581 nightly
The price is $640
Nov 21 - Nov 22
Total with taxes and fees
THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches
An outdoor patio with a grill, seating, and a view of a lake.

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

` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation
East Naples
9.8 out of 10, Exceptional, (10 reviews)
"Great communication and lovely home. "
United States
Anonymous traveler
$364 nightly
The price is $383
Nov 25 - Nov 26
Total with taxes and fees
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation
A pier extending into a clear blue sea with a sandy beach at the end.

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

3BR Golf & Lake View Villa • Pool • Lely Resort
Naples
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful condo that is family friendly and well appointed. Great host and nice location (especially if visiting family in Lely)."
United States
Thomas H.
$376 nightly
The price is $397
Nov 18 - Nov 19
Total with taxes and fees
3BR Golf & Lake View Villa • Pool • Lely Resort
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

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

Free Golf Until Oct! Naples Condo w/ Resort Pool
Naples
9.8 out of 10, Exceptional, (48 reviews)
"Very nice accommodations, the pool area felt like a beautiful resort, and looking out at the golf course was heavenly! We had plenty of space and the washer/dryer was a bonus!Highly recommend."
United States
Colleen V.
$349 nightly
The price is $385
Nov 15 - Nov 16
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A white pergola with climbing plants and pink flowers.

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

Romantic Cottage - With a king, 2 Blocks to Gulf, Old Naples with lit sidewalks.
Old Naples
10.0 out of 10, Exceptional, (22 reviews)
"The host was welcoming and the cottage was just perfect! We loved the location. "
United States
Lynda D.
$807 nightly
The price is $889
Nov 15 - Nov 16
Total with taxes and fees
Romantic Cottage - With a king, 2 Blocks to Gulf, Old Naples with lit sidewalks.
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.
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Top Keewaydin Island Hotel Reviews

Great Wolf Lodge Naples

Great Wolf Lodge Naples

10/10 Excellent
"Super bueno"
Madelaine 3-night trip
Posted 14 hours ago
Great Wolf Lodge Naples

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 $159 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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