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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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

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 1 - Nov 2
Total with taxes and fees
Bellasera Resort
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

2. 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 9 - Nov 10
Total with taxes and fees
Noel Real Estate
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

3. 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 1 - Nov 2
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.

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

Green Turtle Boathouse/HOT TUB view of the canal
East Naples
$458 nightly
The price is $503
Nov 1 - Nov 2
Total with taxes and fees
Green Turtle Boathouse/HOT TUB view of the canal
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.

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.
$614 nightly
The price is $674
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 living room with a gray sofa, a coffee table, and a ceiling fan.

6. 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.
$692 nightly
The price is $760
Nov 10 - Nov 11
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A room with a large window overlooking a pool and a golf course, a blue bench, wicker furniture, and a ceiling fan.

7. 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.
$328 nightly
The price is $344
Nov 1 - Nov 2
Total with taxes and fees
3BR Golf & Lake View Villa • Pool • Lely Resort
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.
$305 nightly
The price is $316
Nov 8 - Nov 9
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.

9. 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 31 - Nov 1
Total with taxes and fees
The Gulfstream Place 2
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

`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.
$299 nightly
The price is $310
Nov 8 - Nov 9
Total with taxes and fees
`The Boho Bliss` - Reset & Recharge Wellness House
A resort with a central swimming pool, multiple buildings, and lush greenery.

11. 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, (23 reviews)
"Great stay."
United States
Kathy R.
$414 nightly
The price is $455
Nov 10 - Nov 11
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
A living room with a large flat-screen TV, a sofa, a coffee table, and a console table with decorative items.

12. 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)
"Perfect location. Thanks for the beach chairs, umbrellas and cart. Wouldn't have been able to enjoy the beach without them!"
United States
Vicki H.
$738 nightly
The price is $810
Nov 15 - Nov 16
Total with taxes and fees
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
A kitchen with a microwave, cabinets, and a ceiling fan. There is a dining area with a table and chairs.

13. 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 31 - Nov 1
Total with taxes and fees
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
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.

14. 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.
$363 nightly
The price is $399
Oct 31 - Nov 1
Total with taxes and fees
Oasis of Naples – Beach & Downtown Haven
A modern kitchen with a dining area, large windows, and a view of an outdoor swimming pool.

15. 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.
$620 nightly
The price is $681
Nov 21 - Nov 22
Total with taxes and fees
THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches
A modern living room with a sofa, coffee table, and a TV. There is a kitchen area with a bar and stools.

16. 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.
$677 nightly
The price is $743
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
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

17. 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.
$307 nightly
The price is $337
Nov 22 - Nov 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.

18. 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.
$225 nightly
The price is $247
Nov 5 - Nov 6
Total with taxes and fees
King Bed Near Pickleball, Beach & Downtown
A modern kitchen with white cabinetry, a dining area with a table and chairs, and a living area with a sofa and a TV.

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.
$584 nightly
The price is $641
Nov 5 - Nov 6
Total with taxes and fees
Coastal Downtown Naples Condo - Walk to the Beach!
A modern kitchen with a central island, a dining area, and a large sliding glass door leading to an outdoor patio.

20. ` 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
$344 nightly
The price is $359
Nov 5 - Nov 6
Total with taxes and fees
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation
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

Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

10/10 Excellent
"All was good"
Doris 2-night trip
Posted 6 hours ago
Compass by Margaritaville Hotel 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 $156 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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