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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Keewaydin Island vacation rentals

A kitchen with a microwave, cabinets, and a ceiling fan. There is a dining area with a table and chairs.

1. 2 Mi to Public Pool! Cozy Naples Cottage w/ Patio

2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
3.0 star property
Naples
$187 nightly
The price is $208
Oct 15 - Oct 16
Total with taxes and fees
2 Mi to Public Pool! Cozy Naples Cottage w/ Patio
A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

2. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,342 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
$342 nightly
The price is $379
Nov 1 - Nov 2
Total with taxes and fees
Bellasera Resort
A single-story house with a front yard, a driveway, and a tree.

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
$377 nightly
The price is $419
Nov 14 - Nov 15
Total with taxes and fees
Noel Real Estate
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.
$203 nightly
The price is $223
Oct 15 - Oct 16
Total with taxes and fees
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A cozy living room with a grey sofa, a small table, and chairs. There is a window with curtains, a lamp, and a mirror on the wall.

5. King Bed Near Pickleball, Beach & Downtown

King Bed Near Pickleball, Beach & Downtown
East Naples
9.8 out of 10, Exceptional, (8 reviews)
"Good communication Decent location Accurate listing"
United States
Francois S.
$246 nightly
The price is $270
Nov 5 - Nov 6
Total with taxes and fees
King Bed Near Pickleball, Beach & Downtown
A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

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

"The Coastal Dream" only 3miles to the beach.
East Naples
9.8 out of 10, Exceptional, (26 reviews)
"Great location, everything was perfect!"
United States
Jesse L.
$295 nightly
The price is $305
Oct 21 - Oct 22
Total with taxes and fees
"The Coastal Dream" only 3miles to the beach.
A modern kitchen with stainless steel appliances, white cabinetry, and a marble countertop.

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
$260 nightly
The price is $285
Oct 15 - Oct 16
Total with taxes and fees
The Gulfstream Place 2
A dining area with a wooden table set for four, wicker chairs, and a ceiling fan.

8. Downtown Naples Retreat - Walk to 5th Ave & Beach

Downtown Naples Retreat - Walk to 5th Ave & Beach
Old Naples
9.4 out of 10, Exceptional, (9 reviews)
"Very clean, nice and quiet, and in a fantastic location. You can walk around the corner to Wynn's Supermarket, which is very upscale. Easy walk to 5th Ave. The owner was wonderful to deal with. Will book again."
United States
Patricia
$334 nightly
The price is $367
Oct 15 - Oct 16
Total with taxes and fees
Downtown Naples Retreat - Walk to 5th Ave & Beach
A modern living room with a white sofa, a dining area with a table and chairs, a large TV on the wall, and a white cabinet.

9. 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.
$371 nightly
The price is $407
Oct 19 - Oct 20
Total with taxes and fees
Oasis of Naples – Beach & Downtown Haven
A resort with a central swimming pool, multiple buildings, and lush greenery.

10. 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)
"Great stay."
United States
Kathy R.
$373 nightly
The price is $409
Oct 19 - Oct 20
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
A white pergola with climbing plants and pink flowers.

11. Romantic Cottage - With a king, 2 Blocks to Gulf, Old Naples with lit sidewalks.

Romantic Cottage - With a king, 2 Blocks to Gulf, Old Naples with lit sidewalks.
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.
$743 nightly
The price is $815
Oct 18 - Oct 19
Total with taxes and fees
Romantic Cottage - With a king, 2 Blocks to Gulf, Old Naples with lit sidewalks.
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

12. 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)
"Very nice accommodations, the pool area felt like a beautiful resort, and looking out at the golf course was heavenly! We had plenty of space and the washer/dryer was a bonus!Highly recommend."
United States
Colleen V.
$366 nightly
The price is $402
Oct 15 - Oct 16
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
A beach with clear skies, palm trees, and calm waves.

13. 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.
$353 nightly
The price is $387
Oct 23 - Oct 24
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
A pier extending into a clear blue sea with a sandy beach at the end.

14. 3BR Golf & Lake View Villa • Pool • Lely Resort

3BR Golf & Lake View Villa • Pool • Lely Resort
Naples
10.0 out of 10, Exceptional, (24 reviews)
"Really enjoyed our stay here. Very clean, and I am very picky. The condo had everything we needed. Plenty of beach chairs, toys, umbrellas. All the kitchen supplies we needed too. I would like to stay here again in the future. "
United States
Karen P.
$334 nightly
The price is $351
Oct 19 - Oct 20
Total with taxes and fees
3BR Golf & Lake View Villa • Pool • Lely Resort
An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

15. 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)
"The hosts are lovely and very accommodating. The location is amazing, close to restaurants and the beach."
United States
Rsandrs100
$625 nightly
The price is $686
Oct 20 - Oct 21
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A wooden pier leading to a beach with clear skies.

16. Coastal Downtown Naples Condo - Walk to the Beach!

Coastal Downtown Naples Condo - Walk to the Beach!
Old Naples
9.8 out of 10, Exceptional, (45 reviews)
"Great location"
United States
Kellie C.
$591 nightly
The price is $648
Nov 5 - Nov 6
Total with taxes and fees
Coastal Downtown Naples Condo - Walk to the Beach!
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.
$247 nightly
The price is $271
Oct 15 - Oct 16
Total with taxes and fees
Steps From The Snook Inn, Olde Marco
A beach with gentle waves and a clear sky.

18. 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)
"The process was smooth and easy"
United States
Brian B.
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr
A compact kitchen with a central island, bar stools, a dining table, and a microwave.

19. 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.
$233 nightly
The price is $256
Oct 23 - Oct 24
Total with taxes and fees
2/1 Hidden Gem
A beach with a variety of seashells and a view of the ocean with waves.

20. 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, (88 reviews)
"Locate close to great restaurants and shoppers"
United States
terry J.
$394 nightly
The price is $426
Oct 20 - Oct 21
Total with taxes and fees
Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
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

Fairways Inn of Naples

Fairways Inn of Naples

10/10 Excellent
"I was surprised. When I arrived, I thought it's an old place that will be run down. I was wrong. They had everything. Perfect outdoor set up. Porches, pool, grilling area, and so on."
William 2-night trip
Posted 1 hour ago
Fairways Inn of 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.

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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