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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$362 nightly
The price is $402
Nov 18 - Nov 19
Total with taxes and fees
Noel Real Estate
A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

2. 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
$342 nightly
The price is $379
Nov 10 - Nov 11
Total with taxes and fees
Bellasera Resort
A kitchen with a microwave, cabinets, and a ceiling fan. There is a dining area with a table and chairs.

3. 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 19 - Oct 20
Total with taxes and fees
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
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.

4. 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.
$246 nightly
The price is $270
Nov 5 - Nov 6
Total with taxes and fees
King Bed Near Pickleball, Beach & Downtown
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, (55 reviews)
"Very cozy house Spent a great time Lovely place"
United States
eric d.
$205 nightly
The price is $225
Oct 19 - Oct 20
Total with taxes and fees
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A modern kitchen with stainless steel appliances, white cabinetry, and a marble countertop.

6. 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
$261 nightly
The price is $286
Oct 19 - Oct 20
Total with taxes and fees
The Gulfstream Place 2
A modern kitchen with a central island, a dining area, and a large sliding glass door leading to an outdoor patio.

7. ` 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
$342 nightly
The price is $357
Oct 24 - Oct 25
Total with taxes and fees
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation
A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

8. "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.
$295 nightly
The price is $305
Oct 21 - Oct 22
Total with taxes and fees
"The Coastal Dream" only 3miles to the beach.
A covered outdoor deck with lounge chairs, a hot tub, and a view of a garden and buildings.

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

Green Turtle Boathouse/HOT TUB view of the canal
East Naples
$425 nightly
The price is $466
Oct 19 - Oct 20
Total with taxes and fees
Green Turtle Boathouse/HOT TUB view of the canal
A resort with a central swimming pool, multiple buildings, and lush greenery.

10. 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.
$381 nightly
The price is $418
Oct 20 - Oct 21
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
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.

11. 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.
$325 nightly
The price is $357
Oct 19 - Oct 20
Total with taxes and fees
Oasis of Naples – Beach & Downtown Haven
A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and a built-in oven.

12. 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.
$266 nightly
The price is $292
Oct 19 - Oct 20
Total with taxes and fees
Steps From The Snook Inn, Olde Marco
A coastal hotel with a central courtyard, a swimming pool, and a marina.

13. 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.
$269 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Margaritaville, Steps From The Snook Inn, Olde Marco
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

14. 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)
"Pool, hot tub, responsive host, exactly what we needed. Private, quiet, pickleball and tennis courts, food nearby, great location, comfy, wonderful huge teddy bear!"
United States
James K.
$352 nightly
The price is $388
Oct 19 - Oct 20
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A pier extending into a clear blue sea with a sandy beach at the end.

15. 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)
"Really enjoyed our stay here. Very clean, and I am very picky. The condo had everything we needed. Plenty of beach chairs, toys, umbrellas. All the kitchen supplies we needed too. I would like to stay here again in the future. "
United States
Karen P.
$331 nightly
The price is $347
Oct 19 - Oct 20
Total with taxes and fees
3BR Golf & Lake View Villa • Pool • Lely Resort
A compact kitchen with a central island, bar stools, a dining table, and a microwave.

16. 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.
$204 nightly
The price is $224
Oct 26 - Oct 27
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.

17. 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
$314 nightly
The price is $345
Oct 19 - Oct 20
Total with taxes and fees
Amazing Olde Marco Condo, Sunsets & Dolphins
An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

18. 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 20 - Oct 21
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A wooden pier leading to a beach with clear skies.

19. Coastal Downtown Naples Condo - Walk to the Beach!

Coastal Downtown Naples Condo - Walk to the Beach!
Old Naples
9.8 out of 10, Exceptional, (45 reviews)
"Great location"
United States
Kellie C.
$591 nightly
The price is $648
Nov 5 - Nov 6
Total with taxes and fees
Coastal Downtown Naples Condo - Walk to the Beach!
A poolside table with a vase of flowers and two champagne flutes, overlooking a pool and palm trees.

20. 🛥️ 👀 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
$336 nightly
The price is $368
Oct 19 - Oct 20
Total with taxes and fees
🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of 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

Hilton Naples

Hilton Naples

8/10 Good
"Toilet paper was vert bad quality, really bad."
Hilda 1-night trip
Posted less than an hour ago
Hilton 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 $138 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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