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

Keewaydin Island Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (2,345 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
$353 nightly
The price is $392
Nov 15 - Nov 16
Total with taxes and fees
Bellasera Resort

2. 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
$361 nightly
The price is $401
Nov 9 - Nov 10
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool

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
$354 nightly
The price is $393
Nov 16 - Nov 17
Total with taxes and fees
Noel Real Estate

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
$344 nightly
The price is $381
Dec 5 - Dec 6
Total with taxes and fees
Park Shore Resort

5. Coastal Paradise

Coastal Paradise
3.0 star property
Old Naples
$618 nightly
The price is $686
Nov 24 - Nov 25
Total with taxes and fees
Coastal Paradise

6. 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
$729 nightly
The price is $809
Nov 16 - Nov 17
Total with taxes and fees
Marriott's Crystal Shores

7. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (300 reviews)
"Everything was exactly like described. It was a great stay."
United States
Jessica
$119 nightly
The price is $132
Nov 9 - Nov 10
Total with taxes and fees
Wiggins Pass Chalet

8. 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
$285 nightly
The price is $301
Nov 9 - Nov 10
Total with taxes and fees
Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby

9. 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
$187 nightly
The price is $208
Nov 9 - Nov 10
Total with taxes and fees
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio

10. 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
$285 nightly
The price is $301
Nov 9 - Nov 10
Total with taxes and fees
Surfside Cottage by Avantstay Patio + BBQ Dog-friendly Lake Access Mins to Gulf Beaches

11. 2 Mi to Beach: Naples Home w/ Pool!

2 Mi to Beach: Naples Home w/ Pool!
3.0 star property
Naples Park
$628 nightly
The price is $697
Nov 9 - Nov 10
Total with taxes and fees
2 Mi to Beach: Naples Home w/ Pool!

12. 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
$285 nightly
The price is $301
Nov 9 - Nov 10
Total with taxes and fees
Seaturtle Cottage by Avantstay Lakefront Patio + Fire Pit Table Workspace Mins to the Beach

13. 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
$285 nightly
The price is $301
Nov 9 - Nov 10
Total with taxes and fees
Fisherman's Cottage by Avantstay Lake Patio + Firepit + Grill Vanderbilt Beach

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
$285 nightly
The price is $301
Nov 9 - Nov 10
Total with taxes and fees
Starfish Cottage by Avantstay Naples Studio Private Patio Near Vanderbilt Beach + Mercato

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

POI Resort Studio Near Everglades NP: Swim + Sail
3.0 star property
Naples
$152 nightly
The price is $169
Nov 9 - Nov 10
Total with taxes and fees
POI Resort Studio Near Everglades NP: Swim + Sail

16. Exclusive 10,000 Islands Access: Naples Studio

Exclusive 10,000 Islands Access: Naples Studio
3.0 star property
Naples
$152 nightly
The price is $169
Nov 9 - Nov 10
Total with taxes and fees
Exclusive 10,000 Islands Access: Naples Studio

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

Everglades Getaway 15 Mi to NP: Sail + Swim!
3.0 star property
Naples
$152 nightly
The price is $169
Nov 9 - Nov 10
Total with taxes and fees
Everglades Getaway 15 Mi to NP: Sail + Swim!

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

Everglades Escape w/ Heated Pool & Marina Access!
3.0 star property
Naples
$152 nightly
The price is $169
Nov 9 - Nov 10
Total with taxes and fees
Everglades Escape w/ Heated Pool & Marina Access!

19. Heated Pool Access: Everglades Resort Retreat!

Heated Pool Access: Everglades Resort Retreat!
3.0 star property
Naples
$152 nightly
The price is $169
Nov 9 - Nov 10
Total with taxes and fees
Heated Pool Access: Everglades Resort Retreat!

20. Resort-style Studio 15 Mi to Everglades NP

Resort-style Studio 15 Mi to Everglades NP
3.0 star property
Naples
$169 nightly
The price is $188
Nov 9 - Nov 10
Total with taxes and fees
Resort-style Studio 15 Mi to Everglades NP
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Keewaydin Island Hotel Reviews

Find out more about Keewaydin Island

Everything you need to know about Keewaydin Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Keewaydin Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Keewaydin Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Keewaydin Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Keewaydin Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Keewaydin Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $132 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Keewaydin Island rentals

At Expedia, we put the best Keewaydin Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Keewaydin Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Keewaydin Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Keewaydin Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia