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. 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
The price is NZ$370
includes taxes & fees
14 Oct - 15 Oct
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio

2. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,341 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
The price is NZ$636
includes taxes & fees
27 Oct - 28 Oct
Bellasera Resort

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$722
includes taxes & fees
14 Oct - 15 Oct
Noel Real Estate

4. 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.
The price is NZ$395
includes taxes & fees
14 Oct - 15 Oct
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

5. 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.
The price is NZ$478
includes taxes & fees
5 Nov - 6 Nov
King Bed Near Pickleball, Beach & Downtown

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, (25 reviews)
"Great location, everything was perfect!"
United States
Jesse L.
The price is NZ$531
includes taxes & fees
21 Oct - 22 Oct
"The Coastal Dream" only 3miles to the beach.

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
The price is NZ$499
includes taxes & fees
25 Oct - 26 Oct
The Gulfstream Place 2

8. Downtown Naples Retreat - Walk to 5th Ave & Beach

Downtown Naples Retreat - Walk to 5th Ave & Beach
Old Naples
9.4 out of 10, Exceptional, (9 reviews)
"Very clean, nice and quiet, and in a fantastic location. You can walk around the corner to Wynn's Supermarket, which is very upscale. Easy walk to 5th Ave. The owner was wonderful to deal with. Will book again."
United States
Patricia
The price is NZ$648
includes taxes & fees
14 Oct - 15 Oct
Downtown Naples Retreat - Walk to 5th Ave & Beach

9. 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.
The price is NZ$742
includes taxes & fees
19 Oct - 20 Oct
Oasis of Naples – Beach & Downtown Haven

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, (21 reviews)
"Great stay."
United States
Kathy R.
The price is NZ$821
includes taxes & fees
26 Oct - 27 Oct
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

11. Romantic Cottage -2 Blocks to the Beach, 5th Street and 3rd Ave. S - Cottage B

Romantic Cottage -2 Blocks to the Beach, 5th Street and 3rd Ave. S - Cottage B
Old Naples
10.0 out of 10, Exceptional, (21 reviews)
"The host was welcoming and the cottage was just perfect! We loved the location. "
United States
Lynda D.
The price is NZ$1,431
includes taxes & fees
18 Oct - 19 Oct
Romantic Cottage -2 Blocks to the Beach, 5th Street and 3rd Ave. S - Cottage B

12. 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.
The price is NZ$708
includes taxes & fees
14 Oct - 15 Oct
Free Golf Until Oct! Naples Condo w/ Resort Pool

13. 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$692
includes taxes & fees
23 Oct - 24 Oct
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

14. 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.
The price is NZ$621
includes taxes & fees
14 Oct - 15 Oct
3BR Golf & Lake View Villa • Pool • Lely Resort

15. 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
The price is NZ$1,166
includes taxes & fees
14 Oct - 15 Oct
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

16. 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.
Coastal Downtown Naples Condo - Walk to the Beach!

17. 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.
The price is NZ$513
includes taxes & fees
21 Oct - 22 Oct
Steps From The Snook Inn, Olde Marco

18. 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)
"The process was smooth and easy"
United States
Brian B.
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr

19. 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$450
includes taxes & fees
23 Oct - 24 Oct
2/1 Hidden Gem

20. 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, (88 reviews)
"Locate close to great restaurants and shoppers"
United States
terry J.
The price is NZ$740
includes taxes & fees
14 Oct - 15 Oct
Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
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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