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

Keewaydin Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Keewaydin Island vacation rentals

A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

1. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,328 reviews)
"The perfect place for a family vacation"
United States
Lorenzo
$256 nightly
The price is $285
Aug 27 - Aug 28
Total with taxes and fees
Bellasera Resort
A white pergola with a brick pathway leading to a house.

2. Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.

Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.
Old Naples
9.8 out of 10, Exceptional, (39 reviews)
"Enjoyed our stay. Clean, stylish, conveniently located to the beach, stores and restaurants. "
United States
Andrew R.
$433 nightly
The price is $474
Aug 27 - Aug 28
Total with taxes and fees
Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

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
$374 nightly
The price is $415
Aug 27 - Aug 28
Total with taxes and fees
Noel Real Estate
A resort with a central swimming pool, multiple buildings, and lush greenery.

4. 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
$351 nightly
The price is $385
Sep 9 - Sep 10
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
A modern kitchen with stainless steel appliances, white cabinetry, and a marble countertop.

5. 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
$263 nightly
The price is $288
Aug 27 - Aug 28
Total with taxes and fees
The Gulfstream Place 2
A swimming pool with clear water, surrounded by palm trees and umbrellas.

6. 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.
$369 nightly
The price is $399
Aug 30 - Aug 31
Total with taxes and fees
Greenlinks Luxury Condo, 3BD, ground floor, golf, pool
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

7. Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
East Naples
9.2 out of 10, Wonderful, (54 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 traveler
$199 nightly
The price is $218
Aug 31 - Sep 1
Total with taxes and fees
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

8. 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.
$371 nightly
The price is $407
Aug 27 - Aug 28
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A covered porch with a wooden ceiling, string lights, a ceiling fan, wicker furniture, and a view of greenery outside.

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.
$382 nightly
The price is $419
Aug 27 - Aug 28
Total with taxes and fees
Cypress Cove
A room with a bed featuring a beach-themed bedspread, a wall with a three-panel artwork depicting a beach scene, and a wooden floor.

10. Cozy 2-bedroom apartment near the Ocean

Cozy 2-bedroom apartment near the Ocean
Naples Park
10.0 out of 10, Exceptional, (18 reviews)
"Staff is great nice friendly and helpful!"
United States
Chad
$212 nightly
The price is $233
Aug 29 - Aug 30
Total with taxes and fees
Cozy 2-bedroom apartment near the Ocean
A beach with clear water, a sandy shore, and a distant shoreline with vegetation.

11. 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.
$488 nightly
The price is $535
Aug 27 - Aug 28
Total with taxes and fees
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr
A modern building entrance with glass doors, a dark exterior, and potted plants on the sides.

12. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (284 reviews)
"Overall it was an awesome stay."
United States
Patricio
$112 nightly
The price is $124
Sep 9 - Sep 10
Total with taxes and fees
Wiggins Pass Chalet
An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

13. 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.
$537 nightly
The price is $589
Sep 1 - Sep 2
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

14. 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
Aug 28 - Aug 29
Total with taxes and fees
Nuevo y Confortable Estudio
A beach with clear skies, palm trees, and calm waves.

15. 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.
$342 nightly
The price is $374
Sep 1 - Sep 2
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
A compact kitchen with a central island, bar stools, a dining table, and a microwave.

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.
$200 nightly
The price is $219
Aug 30 - Aug 31
Total with taxes and fees
2/1 Hidden Gem

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.
$368 nightly
The price is $397
Aug 27 - Aug 28
Total with taxes and fees
Bayfront Condo w/ Sunrise Views & Resort Amenities
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a clear blue sky.

18. 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
Aug 28 - Aug 29
Total with taxes and fees
Overlooking 10th Fairway 2 Free Rounds of Golf
A modern kitchen with dark blue cabinets, a white island, and a dining area with wicker chairs.

19. 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.
$343 nightly
The price is $376
Aug 27 - Aug 28
Total with taxes and fees
2 Miles to the Beach and 5th Ave
A living room with a white sofa, two chairs, a round coffee table, a TV stand, and a window with a view of greenery.

20. Private Suite near the Beach

Private Suite near the Beach
Naples Park
9.4 out of 10, Exceptional, (26 reviews)
"Great little place for a couples quick getaway. "
United States
Nicole Y.
$153 nightly
The price is $168
Aug 27 - Aug 28
Total with taxes and fees
Private Suite near the Beach
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

Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

10/10 Excellent
"👍👍👍"
Stephen 2-night trip
Posted 3 hours ago
Hyatt House Naples/5th Avenue

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 $124 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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