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

Keewaydin Island Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$363 nightly
The price is $403
Oct 31 - Nov 1
Total with taxes and fees
Noel Real Estate
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

2. 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, (55 reviews)
"We had a great visit. Quiet and well kept."
United States
Andrew F.
$203 nightly
The price is $223
Oct 22 - Oct 23
Total with taxes and fees
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
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.

3. 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.
$243 nightly
The price is $267
Nov 5 - Nov 6
Total with taxes and fees
King Bed Near Pickleball, Beach & Downtown
A kitchen with a microwave, cabinets, and a ceiling fan. There is a dining area with a table and chairs.

4. 2 Mi to Public Pool! Cozy Naples Cottage w/ Patio

2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
3.0 star property
Naples
$187 nightly
The price is $208
Oct 22 - Oct 23
Total with taxes and fees
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

5. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,342 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
$345 nightly
The price is $383
Oct 27 - Oct 28
Total with taxes and fees
Bellasera Resort
A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

6. "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.
$294 nightly
The price is $304
Oct 22 - Oct 23
Total with taxes and fees
"The Coastal Dream" only 3miles to the beach.
A modern kitchen with stainless steel appliances, white cabinetry, and a marble countertop.

7. The Gulfstream Place 2

The Gulfstream Place 2
East Naples
9.2 out of 10, Wonderful, (17 reviews)
"Great place for quiet relaxation "
United States
Richard
$260 nightly
The price is $285
Oct 22 - Oct 23
Total with taxes and fees
The Gulfstream Place 2
A modern living room with a white sofa, a dining area with a table and chairs, a large TV on the wall, and a white cabinet.

8. Oasis of Naples – Beach & Downtown Haven

Oasis of Naples – Beach & Downtown Haven
Old Naples
9.4 out of 10, Exceptional, (9 reviews)
"Great place. Great location. Great value! Seamless transaction with the host. "
United States
David C.
$334 nightly
The price is $367
Oct 22 - Oct 23
Total with taxes and fees
Oasis of Naples – Beach & Downtown Haven
A resort with a central swimming pool, multiple buildings, and lush greenery.

9. Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
Naples
10.0 out of 10, Exceptional, (22 reviews)
"Great stay."
United States
Kathy R.
$394 nightly
The price is $433
Oct 27 - Oct 28
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
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
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.
$366 nightly
The price is $402
Oct 22 - Oct 23
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A covered outdoor deck with lounge chairs, a hot tub, and a view of a garden and buildings.

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

Green Turtle Boathouse/HOT TUB view of the canal
East Naples
$424 nightly
The price is $465
Oct 22 - Oct 23
Total with taxes and fees
Green Turtle Boathouse/HOT TUB view of the canal
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.
$202 nightly
The price is $222
Oct 25 - Oct 26
Total with taxes and fees
2/1 Hidden Gem
A modern kitchen with dark blue cabinets, a white island, and a dining area with wicker chairs.

13. 2 Miles to the Beach and 5th Ave

2 Miles to the Beach and 5th Ave
Central Naples
9.6 out of 10, Exceptional, (7 reviews)
"Great location for the price. We would definitely stay again."
United States
Brandon D.
$339 nightly
The price is $372
Oct 24 - Oct 25
Total with taxes and fees
2 Miles to the Beach and 5th Ave
A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and a built-in oven.

14. 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.
$259 nightly
The price is $284
Oct 22 - Oct 23
Total with taxes and fees
Steps From The Snook Inn, Olde Marco
A beach with clear skies, palm trees, and calm waves.

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.
$363 nightly
The price is $398
Nov 2 - Nov 3
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

16. 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, (44 reviews)
"The hosts are lovely and very accommodating. The location is amazing, close to restaurants and the beach."
United States
Rsandrs100
$625 nightly
The price is $686
Oct 22 - Oct 23
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A beach with a variety of seashells and a view of the ocean with waves.

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, (89 reviews)
"Excellent"
United States
Maite
$390 nightly
The price is $422
Oct 26 - Oct 27
Total with taxes and fees
Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
A poolside table with a vase of flowers and two champagne flutes, overlooking a pool and palm trees.

18. 🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of Dolphins🐬

🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of Dolphins🐬
Olde Marco
9.8 out of 10, Exceptional, (58 reviews)
"Comfortable stay, quiet, very clean and nice view. Close to Publix and restaurants."
United States
Clelia
$361 nightly
The price is $396
Oct 22 - Oct 23
Total with taxes and fees
🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of Dolphins🐬
A coastal hotel with a central courtyard, a swimming pool, and a marina.

19. 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)
"Enjoyed our time there, will book again. "
United States
Frank W.
$270 nightly
The price is $296
Oct 22 - Oct 23
Total with taxes and fees
Margaritaville, Steps From The Snook Inn, Olde Marco
A covered outdoor area with a view of a river, docked boats, and a chair with a table.

20. 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
$289 nightly
The price is $319
Oct 22 - Oct 23
Total with taxes and fees
Amazing Olde Marco Condo, Sunsets & Dolphins
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

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

10/10 Excellent
"The only downside was the pool was cold and wish they heated it since there was more of a coldfront here this week."
Lori 6-night trip
Posted 3 hours ago
Naples Beach Club, A Four Seasons Resort

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 $121 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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