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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (2,335 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
$317 nightly
The price is $352
Sep 29 - Sep 30
Total with taxes and fees
Bellasera Resort
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

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
$362 nightly
The price is $402
Oct 29 - Oct 30
Total with taxes and fees
Noel Real Estate
A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

3. "The Coastal Dream" only 3miles to the beach.

"The Coastal Dream" only 3miles to the beach.
East Naples
9.8 out of 10, Exceptional, (25 reviews)
"Great location, everything was perfect!"
United States
Jesse L.
$280 nightly
The price is $290
Oct 25 - Oct 26
Total with taxes and fees
"The Coastal Dream" only 3miles to the beach.
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

4. 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, (55 reviews)
"Very cozy house Spent a great time Lovely place"
United States
eric d.
$170 nightly
The price is $187
Sep 29 - Sep 30
Total with taxes and fees
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful 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
$250 nightly
The price is $275
Sep 29 - Sep 30
Total with taxes and fees
The Gulfstream Place 2
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

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.
$347 nightly
The price is $383
Sep 29 - Sep 30
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A resort with a central swimming pool, multiple buildings, and lush greenery.

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
$344 nightly
The price is $380
Sep 29 - Sep 30
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
A beach with clear skies, palm trees, and calm waves.

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.
$334 nightly
The price is $368
Oct 6 - Oct 7
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
A white pergola with climbing plants and pink flowers.

9. 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.
$591 nightly
The price is $652
Sep 29 - Sep 30
Total with taxes and fees
Romantic Cottage -2 Blocks to the Beach, 5th Street and 3rd Ave. S - Cottage B
An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

10. 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.
$540 nightly
The price is $596
Sep 29 - Sep 30
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

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 29 - Sep 30
Total with taxes and fees
Nuevo y Confortable Estudio
A living room with a blue armchair, a white sofa, and a dining area with a table and chairs.

12. 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.
$406 nightly
The price is $448
Oct 5 - Oct 6
Total with taxes and fees
Awesome Apartment near the Beach
A modern kitchen with dark blue cabinets, a white island, and a dining area with wicker chairs.

13. 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.
$320 nightly
The price is $353
Oct 4 - Oct 5
Total with taxes and fees
2 Miles to the Beach and 5th Ave
A modern building entrance with glass doors, a dark exterior, and potted plants on the sides.

14. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (292 reviews)
"Great location very close to beach and restaurants."
United States
Maribel
$124 nightly
The price is $138
Oct 5 - Oct 6
Total with taxes and fees
Wiggins Pass Chalet
A covered outdoor area with a view of a river, docked boats, and a chair with a table.

15. 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
$274 nightly
The price is $302
Oct 3 - Oct 4
Total with taxes and fees
Amazing Olde Marco Condo, Sunsets & Dolphins
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a clear blue sky.

16. 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 29 - Sep 30
Total with taxes and fees
Overlooking 10th Fairway 2 Free Rounds of Golf
A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and a built-in oven.

17. 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.
$254 nightly
The price is $280
Sep 29 - Sep 30
Total with taxes and fees
Steps From The Snook Inn, Olde Marco
A beach with a long pier extending into the ocean, surrounded by palm trees and a well-maintained lawn.

18. 1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt

1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
Old Naples
9.8 out of 10, Exceptional, (209 reviews)
"Perfect location. Thanks for the beach chairs, umbrellas and cart. Wouldn't have been able to enjoy the beach without them!"
United States
Vicki H.
$570 nightly
The price is $629
Sep 29 - Sep 30
Total with taxes and fees
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
A living room with a white sofa, two chairs, a round coffee table, a TV stand, and a window with a view of greenery.

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.
$162 nightly
The price is $178
Oct 3 - Oct 4
Total with taxes and fees
Private Suite near the Beach
A balcony with a table and chairs, a ceiling fan, and a view of a marina and pool.

20. Marco Island Waterfront Condo. 2 Pools, River & Dolphin View, Walk to Everything

Marco Island Waterfront Condo. 2 Pools, River & Dolphin View, Walk to Everything
Olde Marco
10.0 out of 10, Exceptional, (15 reviews)
"Great condo, beautiful view and excellent location! "
United States
Wendi B.
$391 nightly
The price is $432
Sep 30 - Oct 1
Total with taxes and fees
Marco Island Waterfront Condo. 2 Pools, River & Dolphin View, Walk to Everything
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

The Perry Hotel Naples

The Perry Hotel Naples

10/10 Excellent
"Every room needs a microwave"
Lyly 3-night trip
Posted 1 hour ago
The Perry Hotel Naples

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 $138 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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