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
$377 nightly
The price is $419
Sep 18 - Sep 19
Total with taxes and fees
Noel Real Estate

2. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,331 reviews)
"The perfect place for a family vacation"
United States
Lorenzo
$344 nightly
The price is $382
Sep 10 - Sep 11
Total with taxes and fees
Bellasera Resort

3. ` 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 traveler
$309 nightly
The price is $321
Sep 13 - Sep 14
Total with taxes and fees
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

4. ` The Bohemian Heaven ` w/ SPA, 2miles to downtown

` The Bohemian Heaven ` w/ SPA, 2miles to downtown
East Naples
9.8 out of 10, Exceptional, (17 reviews)
"We would stay here again."
United States
Shane L.
$261 nightly
The price is $271
Sep 10 - Sep 11
Total with taxes and fees
` The Bohemian Heaven ` w/ SPA, 2miles to downtown

5. 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.
$365 nightly
The price is $395
Sep 10 - Sep 11
Total with taxes and fees
Greenlinks Luxury Condo, 3BD, ground floor, golf, pool

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
$260 nightly
The price is $285
Sep 10 - Sep 11
Total with taxes and fees
The Gulfstream Place 2

7. 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.
$366 nightly
The price is $402
Sep 10 - Sep 11
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool

8. 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 traveler
$390 nightly
The price is $428
Sep 16 - Sep 17
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

9. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (289 reviews)
"Great location very close to beach and restaurants."
United States
Maribel
$113 nightly
The price is $125
Sep 23 - Sep 24
Total with taxes and fees
Wiggins Pass Chalet

10. 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.
$393 nightly
The price is $431
Sep 10 - Sep 11
Total with taxes and fees
Cypress Cove

11. 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.
$509 nightly
The price is $561
Sep 11 - Sep 12
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

12. 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
Sep 10 - Sep 11
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool

13. Awesome Apartment near the Beach

Awesome Apartment near the Beach
Central Naples
9.8 out of 10, Exceptional, (23 reviews)
"Great stay"
United States
Steve A.
$399 nightly
The price is $438
Sep 10 - Sep 11
Total with taxes and fees
Awesome Apartment near the Beach

14. 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.
$325 nightly
The price is $357
Sep 11 - Sep 12
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

15. 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.
$472 nightly
The price is $518
Sep 10 - Sep 11
Total with taxes and fees
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr

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.
$214 nightly
The price is $236
Sep 11 - Sep 12
Total with taxes and fees
2/1 Hidden Gem

17. 2 Miles to the Beach and 5th Ave

2 Miles to the Beach and 5th Ave
Central Naples
9.6 out of 10, Exceptional, (7 reviews)
"Great location for the price. We would definitely stay again."
United States
Brandon D.
$338 nightly
The price is $371
Sep 12 - Sep 13
Total with taxes and fees
2 Miles to the Beach and 5th Ave

18. 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.
$140 nightly
The price is $153
Sep 12 - Sep 13
Total with taxes and fees
Nuevo y Confortable Estudio

19. 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.
$371 nightly
The price is $407
Sep 10 - Sep 11
Total with taxes and fees
Boaters Bayshore Bungalow on a Canal with Gulf Access

20. Cozy 2-bedroom apartment near the Ocean

Cozy 2-bedroom apartment near the Ocean
Naples Park
10.0 out of 10, Exceptional, (20 reviews)
"Staff is great nice friendly and helpful!"
United States
Chad
$257 nightly
The price is $282
Sep 10 - Sep 11
Total with taxes and fees
Cozy 2-bedroom apartment near the Ocean
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

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 $125 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.

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