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, (2,315 reviews)
"Hotel was clean and great location"
United States
Rokney
The price is CA $310
CA $407 total
includes taxes & fees
Aug 9 - Aug 10
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 $153
CA $556 total
includes taxes & fees
Sep 8 - Sep 9
Noel Real Estate

3. 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 $164
CA $545 total
includes taxes & fees
Sep 7 - Sep 8
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

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 $125
CA $414 total
includes taxes & fees
Aug 16 - Aug 17
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

5. Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.

Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.
Old Naples
9.8 out of 10, Exceptional, (37 reviews)
"Enjoyed our stay. Clean, stylish, conveniently located to the beach, stores and restaurants. "
United States
Andrew R.
The price is CA $166
CA $656 total
includes taxes & fees
Aug 10 - Aug 11
Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.

6. Swimming pool, lake view, minutes to Naple's downtown and beach.

Swimming pool, lake view, minutes to Naple's downtown and beach.
East Naples
9.2 out of 10, Wonderful, (53 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 CA $210
CA $261 total
includes taxes & fees
Aug 12 - Aug 13
Swimming pool, lake view, minutes to Naple's downtown and beach.

7. "The Coastal Dream" only 3miles to the beach.

"The Coastal Dream" only 3miles to the beach.
East Naples
9.8 out of 10, Exceptional, (23 reviews)
"Nice home, worked well for our short golf getaway."
United States
John B.
The price is CA $125
CA $426 total
includes taxes & fees
Aug 9 - Aug 10
"The Coastal Dream" only 3miles to the beach.

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, (30 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 $519 total
includes taxes & fees
Sep 7 - Sep 8
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

9. 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 $132
CA $214 total
includes taxes & fees
Aug 9 - Aug 10
Nuevo y Confortable Estudio

10. 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 $188
CA $402 total
includes taxes & fees
Aug 11 - Aug 12
The Gulfstream Place 2

11. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (281 reviews)
"The girl on the front desk, when I’ve arrived omg she’s was really nice and excellent customer service I was visiting another places to stay and never someone was very nice like her. 5 stars for her; and the hotel really clean I love it"
United States
Tania
The price is CA $137
CA $152 total
includes taxes & fees
Aug 12 - Aug 13
Wiggins Pass Chalet

12. 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 CA $143
CA $555 total
includes taxes & fees
Aug 9 - Aug 10
Greenlinks Luxury Condo, 3BD, ground floor, golf, pool

13. Private Suite near the Beach

Private Suite near the Beach
Naples Park
9.6 out of 10, Exceptional, (25 reviews)
"Great little place for a couples quick getaway. "
United States
Nicole Y.
The price is CA $41
CA $182 total
includes taxes & fees
Aug 11 - Aug 12
Private Suite near the Beach

14. Centrally Located Boho Private BdR - 7 mi to beach

Centrally Located Boho Private BdR - 7 mi to beach
Naples
8.6 out of 10, Excellent, (11 reviews)
"Clean room, easy to get in and out, wifi was good, and the price was right."
United States
Vivek T.
The price is CA $107
CA $177 total
includes taxes & fees
Aug 21 - Aug 22
Centrally Located Boho Private BdR - 7 mi to beach

15. 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 $202
CA $564 total
includes taxes & fees
Aug 9 - Aug 10
Free Golf Until Oct! Naples Condo w/ Resort Pool

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 $100
CA $301 total
includes taxes & fees
Aug 11 - Aug 12
2/1 Hidden Gem

17. Cypress Cove

Cypress Cove
Naples
10.0 out of 10, Exceptional, (15 reviews)
"This was a wonderful place to stay, clean, spacious with a beautiful yard!"
United States
Rebecca L.
The price is CA $187
CA $578 total
includes taxes & fees
Aug 10 - Aug 11
Cypress Cove

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 CA $277
CA $781 total
includes taxes & fees
Aug 10 - Aug 11
Overlooking 10th Fairway 2 Free Rounds of Golf

19. 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, (86 reviews)
"The condo was perfect for 5 of us for the night we stayed. Great location and had everything we needed."
United States
Jeff K.
The price is CA $116
CA $564 total
includes taxes & fees
Aug 24 - Aug 25
Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)

20. Cozy 2-bedroom house in tranquil Marco Island with AC

Cozy 2-bedroom house in tranquil Marco Island with AC
Marco Island
10.0 out of 10, Exceptional, (12 reviews)
"First little getaway with my girlfriend & I. We enjoyed our stay, it was very welcoming home, quiet neighborhood, & Paula was easy to communicate with. Needless to say, we will be staying again in the near future :)."
United States
Brandon R.
The price is CA $209
CA $524 total
includes taxes & fees
Aug 21 - Aug 22
Cozy 2-bedroom house in tranquil Marco Island with AC
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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