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 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Keewaydin Island vacation rentals

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

1. 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
$360 nightly
The price is $400
Dec 6 - Dec 7
Total with taxes and fees
Noel Real Estate
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.

2. 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.
$217 nightly
The price is $239
Nov 9 - Nov 10
Total with taxes and fees
King Bed Near Pickleball, Beach & Downtown
A modern kitchen with a central island, wooden stools, and a sliding glass door leading to a patio.

3. `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.
$275 nightly
The price is $286
Nov 8 - Nov 9
Total with taxes and fees
`The Boho Bliss` - Reset & Recharge Wellness House
A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

4. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,344 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
$353 nightly
The price is $392
Nov 10 - Nov 11
Total with taxes and fees
Bellasera Resort
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

5. 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
An indoor pool area with a glass floor, seating around the pool, and a bar area with a blue ceiling and hanging lights.

6. 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
$218 nightly
The price is $242
Nov 8 - Nov 9
Total with taxes and fees
Park Shore Resort
A white pergola with a brick pathway leading to a house.

7. 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.
$557 nightly
The price is $616
Nov 30 - Dec 1
Total with taxes and fees
Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.
A modern kitchen with a dining area, large windows, and a view of an outdoor swimming pool.

8. 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.
$597 nightly
The price is $658
Nov 21 - Nov 22
Total with taxes and fees
THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

9. 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.
$336 nightly
The price is $372
Nov 8 - Nov 9
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

10. 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 8 - Nov 9
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and a built-in oven.

11. Steps From The Snook Inn, Olde Marco

Steps From The Snook Inn, Olde Marco
Olde Marco
10.0 out of 10, Exceptional, (12 reviews)
"Nice, clean and wonderful location. Communication with host very easy. Highly recommend!"
United States
Lucyna R.
$249 nightly
The price is $274
Nov 6 - Nov 7
Total with taxes and fees
Steps From The Snook Inn, Olde Marco
A compact kitchen with a central island, bar stools, a dining table, and a microwave.

12. 2/1 Hidden Gem

2/1 Hidden Gem
Naples
9.8 out of 10, Exceptional, (18 reviews)
"Exactly what we needed - comfy bed, great location, exceptional hosts! Will definitely stay again!!"
United States
Katherine S.
$203 nightly
The price is $224
Nov 9 - Nov 10
Total with taxes and fees
2/1 Hidden Gem
A covered outdoor area with a view of a river, docked boats, and a chair with a table.

13. Amazing Olde Marco Condo, Sunsets & Dolphins

Amazing Olde Marco Condo, Sunsets & Dolphins
Olde Marco
9.8 out of 10, Exceptional, (56 reviews)
"This condo was perfect! It’s in a quiet area right on the canal. However, many things to do/places to eat & drink within minutes. The condo is beautiful inside and very well maintained. Really enjoyed sitting on the balcony and watching the nature around there. Highly recommend this place!"
United States
Michelle
$274 nightly
The price is $302
Nov 7 - Nov 8
Total with taxes and fees
Amazing Olde Marco Condo, Sunsets & Dolphins
A coastal hotel with a central courtyard, a swimming pool, and a marina.

14. Margaritaville, Steps From The Snook Inn, Olde Marco

Margaritaville, Steps From The Snook Inn, Olde Marco
Olde Marco
9.4 out of 10, Exceptional, (64 reviews)
"Perfect for a quick weekend getaway. Our host, Darin, was communicative. The property was clean and cutely decorated. oh and the BEDS were a dream- honestly one of the most comfortable I have ever slept on. The property was perfectly located - always a plus when a favorite entertainment spot is walking distance."
United States
Frannie L.
$279 nightly
The price is $307
Nov 7 - Nov 8
Total with taxes and fees
Margaritaville, Steps From The Snook Inn, Olde Marco
A modern kitchen with a stainless steel sink, a dining area with a glass table and chairs, and a chandelier.

15. Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
Central Naples
10.0 out of 10, Exceptional, (31 reviews)
"Host was very helpful, responded promptly to all communication and we will stay there again."
United States
Rick B.
$350 nightly
The price is $385
Nov 19 - Nov 20
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
A resort with a swimming pool, palm trees, and a view of the water.

16. Water View of Marco Pass, Heated Pool & Marina-Newly Updated 5th Floor 1Br/1Ba

Water View of Marco Pass, Heated Pool & Marina-Newly Updated 5th Floor 1Br/1Ba
Olde Marco
9.8 out of 10, Exceptional, (142 reviews)
"The balcony was a peaceful place to sit. The hot tub and pool had perfect temperatures and we spent a good deal of time enjoying those. Bike rental, restaurant choices and grocery stores are super close."
United States
Andrew H.
$267 nightly
The price is $294
Nov 11 - Nov 12
Total with taxes and fees
Water View of Marco Pass, Heated Pool & Marina-Newly Updated 5th Floor 1Br/1Ba
A balcony with wicker furniture, a table with wine glasses, and a view of palm trees and a street.

17. Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)

Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
Marco Island
9.6 out of 10, Exceptional, (90 reviews)
"Excellent"
United States
Maite
$387 nightly
The price is $420
Nov 15 - Nov 16
Total with taxes and fees
Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
A covered outdoor deck with lounge chairs, a hot tub, and a view of a garden and buildings.

18. 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 6 - Nov 7
Total with taxes and fees
Green Turtle Boathouse/HOT TUB view of the canal
A modern living room with a gray sofa, a coffee table, and a ceiling fan.

19. 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 6 - Nov 7
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A modern living room with a sofa, coffee table, and a TV. There is a kitchen area with a bar and stools.

20. THE TERRANOVA, Heated Pool, 10 Min to 5th Ave/Beach 5 min to US Open Pickleball

THE TERRANOVA, Heated Pool, 10 Min to 5th Ave/Beach 5 min to US Open Pickleball
East Naples
10.0 out of 10, Exceptional, (33 reviews)
"Loved our stay at this lovely home! It was perfect for our family of 5. "
United States
Olga F.
$649 nightly
The price is $715
Nov 10 - Nov 11
Total with taxes and fees
THE TERRANOVA, Heated Pool, 10 Min to 5th Ave/Beach 5 min to US Open Pickleball
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

La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

10/10 Excellent
"Great place very easy to get in and out of."
Steven 3-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Naples Downtown

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 $153 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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