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

Keewaydin Island Vacation Rentals

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Our top choices for Keewaydin Island vacation rentals

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
The price is CA $157
CA $569 total
includes taxes & fees
Nov 16 - Nov 17
Noel Real Estate

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
The price is CA $400
CA $507 total
includes taxes & fees
Oct 18 - Oct 19
Bellasera Resort

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
The price is CA $179
CA $295 total
includes taxes & fees
Oct 18 - Oct 19
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio

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.
The price is CA $149
CA $384 total
includes taxes & fees
Nov 5 - Nov 6
King Bed Near Pickleball, Beach & Downtown

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.
The price is CA $156
CA $319 total
includes taxes & fees
Oct 18 - Oct 19
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

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
The price is CA $192
CA $409 total
includes taxes & fees
Oct 18 - Oct 19
The Gulfstream Place 2

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 traveller
The price is CA $192
CA $509 total
includes taxes & fees
Oct 30 - Oct 31
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

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.
The price is CA $128
CA $434 total
includes taxes & fees
Oct 22 - Oct 23
"The Coastal Dream" only 3miles to the beach.

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

Green Turtle Boathouse/HOT TUB view of the canal
East Naples
The price is CA $332
CA $657 total
includes taxes & fees
Oct 18 - Oct 19
Green Turtle Boathouse/HOT TUB view of the canal

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.
The price is CA $187
CA $589 total
includes taxes & fees
Oct 19 - Oct 20
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

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.
The price is CA $137
CA $522 total
includes taxes & fees
Oct 17 - Oct 18
Oasis of Naples – Beach & Downtown Haven

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.
The price is CA $176
CA $417 total
includes taxes & fees
Oct 17 - Oct 18
Steps From The Snook Inn, Olde Marco

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.
The price is CA $190
CA $434 total
includes taxes & fees
Oct 17 - Oct 18
Margaritaville, Steps From The Snook Inn, Olde Marco

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)
"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 CA $206
CA $570 total
includes taxes & fees
Oct 18 - Oct 19
Free Golf Until Oct! Naples Condo w/ Resort Pool

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.
The price is CA $200
CA $494 total
includes taxes & fees
Oct 19 - Oct 20
3BR Golf & Lake View Villa • Pool • Lely Resort

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 CA $114
CA $321 total
includes taxes & fees
Oct 25 - Oct 26
2/1 Hidden Gem

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
The price is CA $240
CA $492 total
includes taxes & fees
Oct 17 - Oct 18
Amazing Olde Marco Condo, Sunsets & Dolphins

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
The price is CA $424
CA $985 total
includes taxes & fees
Oct 20 - Oct 21
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

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.
The price is CA $460
CA $919 total
includes taxes & fees
Nov 5 - Nov 6
Coastal Downtown Naples Condo - Walk to the Beach!

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
The price is CA $192
CA $520 total
includes taxes & fees
Oct 18 - Oct 19
🛥️ 👀 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

Find out more about Keewaydin Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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