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

Keewaydin Island Holiday Rentals

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Our top choices for Keewaydin Island holiday rentals

1. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,328 reviews)
"The perfect place for a family vacation"
United States
Lorenzo
The price is NZ$450
includes taxes & fees
29 Sept - 30 Sept
Bellasera Resort

2. 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.
Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.

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
The price is NZ$672
includes taxes & fees
31 Aug - 1 Sept
Noel Real Estate

4. 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, (21 reviews)
"The property was beautiful and perfect for our week in Florida. The condo is spacious and clean with all the essentials supplied. The pool was very close and very relaxing. We loved staying here and hope to return in the future."
United States
Anonymous traveller
The price is NZ$750
includes taxes & fees
23 Sept - 24 Sept
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

5. 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
The price is NZ$479
includes taxes & fees
30 Aug - 31 Aug
The Gulfstream Place 2

6. Greenlinks Luxury Condo, 3BD, ground floor, golf, pool

Greenlinks Luxury Condo, 3BD, ground floor, golf, pool
Naples
9.8 out of 10, Exceptional, (30 reviews)
"Easy stay"
United States
CANDI E.
The price is NZ$663
includes taxes & fees
30 Aug - 31 Aug
Greenlinks Luxury Condo, 3BD, ground floor, golf, pool

7. 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, (54 reviews)
"Everything was so nice, met the host they were very kind too, pool was so nice so was the access, loved it!"
United States
Anonymous traveller
The price is NZ$363
includes taxes & fees
30 Aug - 31 Aug
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

8. 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.
The price is NZ$675
includes taxes & fees
30 Aug - 31 Aug
Free Golf Until Oct! Naples Condo w/ Resort Pool

9. 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.
The price is NZ$697
includes taxes & fees
30 Aug - 31 Aug
Cypress Cove

10. Cozy 2-bedroom apartment near the Ocean

Cozy 2-bedroom apartment near the Ocean
Naples Park
10.0 out of 10, Exceptional, (19 reviews)
"Staff is great nice friendly and helpful!"
United States
Chad
The price is NZ$398
includes taxes & fees
30 Aug - 31 Aug
Cozy 2-bedroom apartment near the Ocean

11. Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr

Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr
Central Naples
10.0 out of 10, Exceptional, (27 reviews)
"Property owner was very responsive and property is as described from listing and other reviews. Great location very central to everything! Great choice! "
United States
Reid D.
The price is NZ$956
includes taxes & fees
1 Sept - 2 Sept
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr

12. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (284 reviews)
"Overall it was an awesome stay."
United States
Patricio
The price is NZ$184
includes taxes & fees
14 Sept - 15 Sept
Wiggins Pass Chalet

13. 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)
"We had a great time! The location was amazing…a few steps to the beach and a few to downtown in the other direction. The place and beds were comfortable and it was well-stocked! Will come again!"
United States
Sheila N.
The price is NZ$979
includes taxes & fees
1 Sept - 2 Sept
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

14. Nuevo y Confortable Estudio

Nuevo y Confortable Estudio
Naples
8.6 out of 10, Excellent, (14 reviews)
"The place was easy to find and directions were very clear."
United States
Laura C.
The price is NZ$257
includes taxes & fees
30 Aug - 31 Aug
Nuevo y Confortable Estudio

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.
The price is NZ$612
includes taxes & fees
1 Sept - 2 Sept
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

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.
The price is NZ$361
includes taxes & fees
31 Aug - 1 Sept
2/1 Hidden Gem

17. Bayfront Condo w/ Sunrise Views & Resort Amenities

Bayfront Condo w/ Sunrise Views & Resort Amenities
Olde Marco
9.6 out of 10, Exceptional, (10 reviews)
"Great condo , location, and marina . We very much enjoyed our stay"
United States
Ted S.
The price is NZ$664
includes taxes & fees
31 Aug - 1 Sept
Bayfront Condo w/ Sunrise Views & Resort Amenities

18. Overlooking 10th Fairway 2 Free Rounds of Golf

Overlooking 10th Fairway 2 Free Rounds of Golf
3.5 star property
Naples
The price is NZ$941
includes taxes & fees
3 Sept - 4 Sept
Overlooking 10th Fairway 2 Free Rounds of Golf

19. 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.
The price is NZ$625
includes taxes & fees
30 Aug - 31 Aug
2 Miles to the Beach and 5th Ave

20. Private Suite near the Beach

Private Suite near the Beach
Naples Park
9.4 out of 10, Exceptional, (26 reviews)
"Great little place for a couples quick getaway. "
United States
Nicole Y.
The price is NZ$282
includes taxes & fees
30 Aug - 31 Aug
Private Suite near the Beach
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

Find out more about Keewaydin Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Keewaydin Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Keewaydin Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Keewaydin Island. Seeing all the best attractions is bound to make you fall in love with Keewaydin Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Keewaydin Island short-term rentals, that won’t be hard to do.

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