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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
Downtown
9.6 out of 10, Exceptional, (2,346 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
The price is CA $431
CA $541 total
includes taxes & fees
Nov 18 - Nov 19
Bellasera Resort

2. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (303 reviews)
"Staff were super helpful."
Australia
Donna
The price is CA $196
CA $217 total
includes taxes & fees
Nov 16 - Nov 17
Wiggins Pass Chalet

3. Marriott's Crystal Shores

Marriott's Crystal Shores
3.5 star property
South End
9.2 out of 10, Wonderful, (248 reviews)
"Room and property very clean. great activities for the kids daily"
United States
Rebecca
The price is CA $1,083
CA $1,202 total
includes taxes & fees
Dec 7 - Dec 8
Marriott's Crystal Shores

4. Park Shore Resort

Park Shore Resort
3.0 star property
Park Shore
8.8 out of 10, Excellent, (733 reviews)
"I have been going there for over 30 years, and park shore never disappoints. We love the atmosphere and the tranquility."
United States
nathaly
The price is CA $311
CA $527 total
includes taxes & fees
Dec 5 - Dec 6
Park Shore Resort

5. 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 $154
CA $567 total
includes taxes & fees
Dec 15 - Dec 16
Noel Real Estate

6. Free Golf Until Oct! Naples Condo w/ Resort Pool

Free Golf Until Oct! Naples Condo w/ Resort Pool
3.5 star property
Naples
10.0 out of 10, Exceptional, (1 review)
"We spent a weekend here while visiting family in the area. Great location for us. Super friendly and helpful. Nice sunset view over the golf course. "
United States
Mark
The price is CA $271
CA $572 total
includes taxes & fees
Nov 16 - Nov 17
Free Golf Until Oct! Naples Condo w/ Resort Pool

7. Surfside Cottage by Avantstay Patio + BBQ Dog-friendly Lake Access Mins to Gulf Beaches

Surfside Cottage by Avantstay Patio + BBQ Dog-friendly Lake Access Mins to Gulf Beaches
3.0 star property
Naples Park
The price is CA $223
CA $456 total
includes taxes & fees
Nov 17 - Nov 18
Surfside Cottage by Avantstay Patio + BBQ Dog-friendly Lake Access Mins to Gulf Beaches

8. Coastal Paradise

Coastal Paradise
3.0 star property
Old Naples
The price is CA $427
CA $915 total
includes taxes & fees
Nov 30 - Dec 1
Coastal Paradise

9. 2 Mi to Beach: Naples Home w/ Pool!

2 Mi to Beach: Naples Home w/ Pool!
3.0 star property
Naples Park
The price is CA $372
CA $995 total
includes taxes & fees
Nov 16 - Nov 17
2 Mi to Beach: Naples Home w/ Pool!

10. Fisherman's Cottage by Avantstay Lake Patio + Firepit + Grill Vanderbilt Beach

Fisherman's Cottage by Avantstay Lake Patio + Firepit + Grill Vanderbilt Beach
3.0 star property
Naples Park
The price is CA $223
CA $479 total
includes taxes & fees
Nov 16 - Nov 17
Fisherman's Cottage by Avantstay Lake Patio + Firepit + Grill Vanderbilt Beach

11. 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 $180
CA $296 total
includes taxes & fees
Nov 29 - Nov 30
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio

12. Naples Duplex Home w/ Private Pool & Lanai!

Naples Duplex Home w/ Private Pool & Lanai!
3.0 star property
Naples
The price is CA $283
CA $846 total
includes taxes & fees
Dec 9 - Dec 10
Naples Duplex Home w/ Private Pool & Lanai!

13. POI Resort Studio Near Everglades NP: Swim + Sail

POI Resort Studio Near Everglades NP: Swim + Sail
3.0 star property
Naples
The price is CA $130
CA $241 total
includes taxes & fees
Nov 16 - Nov 17
POI Resort Studio Near Everglades NP: Swim + Sail

14. Starfish Cottage by Avantstay Naples Studio Private Patio Near Vanderbilt Beach + Mercato

Starfish Cottage by Avantstay Naples Studio Private Patio Near Vanderbilt Beach + Mercato
3.0 star property
Naples Park
The price is CA $223
CA $456 total
includes taxes & fees
Nov 16 - Nov 17
Starfish Cottage by Avantstay Naples Studio Private Patio Near Vanderbilt Beach + Mercato

15. Seaturtle Cottage by Avantstay Lakefront Patio + Fire Pit Table Workspace Mins to the Beach

Seaturtle Cottage by Avantstay Lakefront Patio + Fire Pit Table Workspace Mins to the Beach
3.0 star property
Naples Park
The price is CA $230
CA $464 total
includes taxes & fees
Nov 23 - Nov 24
Seaturtle Cottage by Avantstay Lakefront Patio + Fire Pit Table Workspace Mins to the Beach

16. Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby

Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby
3.0 star property
Naples Park
The price is CA $224
CA $457 total
includes taxes & fees
Nov 22 - Nov 23
Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby

17. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
3.0 star property
Naples
The price is CA $130
CA $241 total
includes taxes & fees
Nov 16 - Nov 17
Exclusive 10,000 Islands Access: Naples Studio

18. Everglades Getaway 15 Mi to NP: Sail + Swim!

Everglades Getaway 15 Mi to NP: Sail + Swim!
3.0 star property
Naples
The price is CA $130
CA $241 total
includes taxes & fees
Nov 16 - Nov 17
Everglades Getaway 15 Mi to NP: Sail + Swim!

19. Everglades Escape w/ Heated Pool & Marina Access!

Everglades Escape w/ Heated Pool & Marina Access!
3.0 star property
Naples
The price is CA $130
CA $241 total
includes taxes & fees
Nov 16 - Nov 17
Everglades Escape w/ Heated Pool & Marina Access!

20. Dock, Pool & Tennis Courts: Naples Resort Retreat!

Dock, Pool & Tennis Courts: Naples Resort Retreat!
3.0 star property
Naples
The price is CA $156
CA $270 total
includes taxes & fees
Nov 16 - Nov 17
Dock, Pool & Tennis Courts: Naples Resort Retreat!
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.