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. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,333 reviews)
"Great place , near to fifth ave ."
United States
Mavelys
The price is CA $378
CA $482 total
includes taxes & fees
Sep 28 - Sep 29
Bellasera Resort

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
The price is CA $160
CA $566 total
includes taxes & fees
Oct 15 - Oct 16
Noel Real Estate

3. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (291 reviews)
"Great location very close to beach and restaurants."
United States
Maribel
The price is CA $152
CA $168 total
includes taxes & fees
Sep 27 - Sep 28
Wiggins Pass Chalet

4. ` 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 $140
CA $415 total
includes taxes & fees
Oct 5 - Oct 6
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

5. 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 CA $189
CA $589 total
includes taxes & fees
Sep 28 - Sep 29
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

6. 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 CA $203
CA $559 total
includes taxes & fees
Sep 27 - Sep 28
Free Golf Until Oct! Naples Condo w/ Resort Pool

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 CA $189
CA $399 total
includes taxes & fees
Sep 29 - Sep 30
The Gulfstream Place 2

8. 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 CA $132
CA $517 total
includes taxes & fees
Sep 24 - Sep 25
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

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 CA $206
CA $607 total
includes taxes & fees
Sep 25 - Sep 26
Cypress Cove

10. 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 CA $131
CA $772 total
includes taxes & fees
Sep 23 - Sep 24
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr

11. 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 CA $147
CA $230 total
includes taxes & fees
Sep 29 - Sep 30
Nuevo y Confortable Estudio

12. 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 CA $292
CA $960 total
includes taxes & fees
Sep 23 - Sep 24
Romantic Cottage -2 Blocks to the Beach, 5th Street and 3rd Ave. S - Cottage B

13. 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 $209
CA $448 total
includes taxes & fees
Sep 23 - Sep 24
Amazing Olde Marco Condo, Sunsets & Dolphins

14. 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 CA $351
CA $878 total
includes taxes & fees
Sep 29 - Sep 30
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

15. Overlooking 10th Fairway 2 Free Rounds of Golf

Overlooking 10th Fairway 2 Free Rounds of Golf
3.5 star property
Naples
The price is CA $278
CA $784 total
includes taxes & fees
Sep 27 - Sep 28
Overlooking 10th Fairway 2 Free Rounds of Golf

16. Boaters Bayshore Bungalow on a Canal with Gulf Access

Boaters Bayshore Bungalow on a Canal with Gulf Access
East Naples
9.6 out of 10, Exceptional, (19 reviews)
"We had a great time at this lovely bungalow. It was cozy, spotlessly clean, and the patio was a wonderful bonus. Highly recommend this property for a relaxing stay."
United States
Katarina O.
The price is CA $293
CA $546 total
includes taxes & fees
Sep 26 - Sep 27
Boaters Bayshore Bungalow on a Canal with Gulf Access

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 CA $250
CA $618 total
includes taxes & fees
Sep 27 - Sep 28
Bayfront Condo w/ Sunrise Views & Resort Amenities

18. 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 $199
CA $594 total
includes taxes & fees
Sep 29 - Sep 30
Oasis of Naples – Beach & Downtown Haven

19. Private Suite near the Beach

Private Suite near the Beach
Naples Park
9.4 out of 10, Exceptional, (27 reviews)
"Great little place for a couples quick getaway. "
United States
Nicole Y.
The price is CA $95
CA $242 total
includes taxes & fees
Sep 26 - Sep 27
Private Suite near 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, (57 reviews)
"Comfortable stay, quiet, very clean and nice view. Close to Publix and restaurants."
United States
Clelia
The price is CA $232
CA $562 total
includes taxes & fees
Sep 23 - Sep 24
🛥️ 👀 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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