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
$314 nightly
The price is $348
Sep 24 - Sep 25
Total with taxes and fees
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
$373 nightly
The price is $414
Sep 23 - Sep 24
Total with taxes and fees
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
$113 nightly
The price is $125
Sep 23 - Sep 24
Total with taxes and fees
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 traveler
$288 nightly
The price is $299
Oct 5 - Oct 6
Total with taxes and fees
` 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 traveler
$378 nightly
The price is $415
Sep 28 - Sep 29
Total with taxes and fees
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.
$369 nightly
The price is $405
Sep 23 - Sep 24
Total with taxes and fees
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
$262 nightly
The price is $287
Sep 23 - Sep 24
Total with taxes and fees
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.
$339 nightly
The price is $371
Sep 24 - Sep 25
Total with taxes and fees
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.
$392 nightly
The price is $430
Sep 25 - Sep 26
Total with taxes and fees
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.
$503 nightly
The price is $552
Sep 23 - Sep 24
Total with taxes and fees
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.
$150 nightly
The price is $164
Sep 28 - Sep 29
Total with taxes and fees
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.
$627 nightly
The price is $688
Sep 23 - Sep 24
Total with taxes and fees
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
$279 nightly
The price is $307
Sep 23 - Sep 24
Total with taxes and fees
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.
$574 nightly
The price is $630
Sep 23 - Sep 24
Total with taxes and fees
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
$505 nightly
The price is $560
Sep 24 - Sep 25
Total with taxes and fees
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.
$374 nightly
The price is $410
Sep 23 - Sep 24
Total with taxes and fees
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.
$411 nightly
The price is $444
Sep 27 - Sep 28
Total with taxes and fees
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.
$375 nightly
The price is $412
Sep 24 - Sep 25
Total with taxes and fees
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.
$158 nightly
The price is $173
Sep 26 - Sep 27
Total with taxes and fees
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
$367 nightly
The price is $403
Sep 23 - Sep 24
Total with taxes and fees
🛥️ 👀 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

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.

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.

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