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 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Keewaydin Island vacation rentals

Lobby

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
$285 nightly
The price is $317
Sep 6 - Sep 7
Total with taxes and fees
Bellasera Resort
Apartment, Patio, Garden View | Private kitchen

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
$374 nightly
The price is $415
Sep 19 - Sep 20
Total with taxes and fees
Noel Real Estate
Property entrance

3. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (286 reviews)
"Overall it was an awesome stay."
United States
Patricio
$111 nightly
The price is $123
Sep 24 - Sep 25
Total with taxes and fees
Wiggins Pass Chalet
Private kitchen

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
$313 nightly
The price is $325
Sep 13 - Sep 14
Total with taxes and fees
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation
Beach

5. 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.
$338 nightly
The price is $370
Sep 6 - Sep 7
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
Pool

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.
$370 nightly
The price is $406
Sep 7 - Sep 8
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
Exterior

7. 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
$392 nightly
The price is $430
Sep 7 - Sep 8
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
Pool

8. 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.
$388 nightly
The price is $420
Sep 8 - Sep 9
Total with taxes and fees
Greenlinks Luxury Condo, 3BD, ground floor, golf, pool
Private kitchen

9. 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
$259 nightly
The price is $284
Sep 5 - Sep 6
Total with taxes and fees
The Gulfstream Place 2
Living area

10. 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.
$424 nightly
The price is $465
Sep 6 - Sep 7
Total with taxes and fees
Awesome Apartment near the Beach
Beach

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.
$478 nightly
The price is $524
Sep 9 - Sep 10
Total with taxes and fees
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr
Apartment (2 Bedrooms) | Interior

12. 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 6 - Sep 7
Total with taxes and fees
Overlooking 10th Fairway 2 Free Rounds of Golf
Private kitchen

13. Steps From The Snook Inn, Olde Marco

Steps From The Snook Inn, Olde Marco
Olde Marco
10.0 out of 10, Exceptional, (12 reviews)
"Nice, clean and wonderful location. Communication with host very easy. Highly recommend!"
United States
Lucyna R.
$279 nightly
The price is $307
Sep 5 - Sep 6
Total with taxes and fees
Steps From The Snook Inn, Olde Marco
Private kitchen

14. 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.
$225 nightly
The price is $247
Sep 7 - Sep 8
Total with taxes and fees
2/1 Hidden Gem
Room

15. 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
Beach

16. 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 11 - Sep 12
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
Room

17. 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
$250 nightly
The price is $275
Sep 6 - Sep 7
Total with taxes and fees
Cozy 2-bedroom apartment near the Ocean
Living area

18. 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.
$158 nightly
The price is $173
Sep 5 - Sep 6
Total with taxes and fees
Private Suite near the Beach
Beach

19. Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)

Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
Marco Island
9.6 out of 10, Exceptional, (87 reviews)
"Locate close to great restaurants and shoppers"
United States
terry J.
$385 nightly
The price is $417
Sep 8 - Sep 9
Total with taxes and fees
Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
Exterior

20. Margaritaville, Steps From The Snook Inn, Olde Marco

Margaritaville, Steps From The Snook Inn, Olde Marco
Olde Marco
9.4 out of 10, Exceptional, (63 reviews)
"Enjoyed our time there, will book again. "
United States
Frank W.
$299 nightly
The price is $330
Sep 5 - Sep 6
Total with taxes and fees
Margaritaville, Steps From The Snook Inn, Olde Marco
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

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

10/10 Excellent
"WE WERE VERY HAPPY WITH THE ROOM, SERVICE AND CHILDREN ACTIVITIES. SUPER CLOSE TO THE BEACH. THE ONLY THING WE DIDN'T LIKE WAS THEY WANTED TO CHARGE MORE MONEY FOR A LATE CHECK OUT. MOST HOTEL ALLOW YOU TO DO THAT WITHOUT AN EXTRA CHARGE."
Steven 2-night trip
Posted less than an hour ago
Hilton Marco Island Beach Resort and Spa

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 $123 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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