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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 7 - Oct 8
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, (2,339 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 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
$363 nightly
The price is $403
Oct 14 - Oct 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.
$204 nightly
The price is $224
Oct 7 - Oct 8
Total with taxes and fees
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

5. "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.
$292 nightly
The price is $302
Oct 21 - Oct 22
Total with taxes and fees
"The Coastal Dream" only 3miles to the beach.
A modern kitchen with a central island, a dining area, and a large sliding glass door leading to an outdoor patio.

6. ` 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
$300 nightly
The price is $311
Oct 8 - Oct 9
Total with taxes and fees
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation
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 7 - Oct 8
Total with taxes and fees
The Gulfstream Place 2
A resort with a central swimming pool, multiple buildings, and lush greenery.

8. 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.
$381 nightly
The price is $418
Oct 19 - Oct 20
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
A compact kitchen with a central island, bar stools, a dining table, and a microwave.

9. 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.
$234 nightly
The price is $257
Oct 10 - Oct 11
Total with taxes and fees
2/1 Hidden Gem
A pier extending into a clear blue sea with a sandy beach at the end.

10. 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.
$330 nightly
The price is $347
Oct 7 - Oct 8
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.

11. 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
$603 nightly
The price is $662
Oct 11 - Oct 12
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A white pergola with climbing plants and pink flowers.

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.
$643 nightly
The price is $706
Oct 7 - Oct 8
Total with taxes and fees
Romantic Cottage -2 Blocks to the Beach, 5th Street and 3rd Ave. S - Cottage B
A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

13. 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.
$366 nightly
The price is $402
Oct 7 - Oct 8
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
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.

14. 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.
$415 nightly
The price is $456
Oct 7 - Oct 8
Total with taxes and fees
Oasis of Naples – Beach & Downtown Haven
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.
$358 nightly
The price is $392
Oct 18 - Oct 19
Total with taxes and fees
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
A poolside table with a vase of flowers and two champagne flutes, overlooking a pool and palm trees.

16. 🛥️ 👀 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
$333 nightly
The price is $365
Oct 8 - Oct 9
Total with taxes and fees
🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of Dolphins🐬
A bedroom with a bed, a ceiling fan, a TV, and a bathroom visible through an open door.

17. Modern 2-unit Combo w/ Pool: 'naples Hideaway'

Modern 2-unit Combo w/ Pool: 'naples Hideaway'
3.0 star property
Naples
$737 nightly
The price is $818
Nov 2 - Nov 3
Total with taxes and fees
Modern 2-unit Combo w/ Pool: 'naples Hideaway'
A modern kitchen with dark blue cabinets, a white island, and a dining area with wicker chairs.

18. 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
Oct 12 - Oct 13
Total with taxes and fees
2 Miles to the Beach and 5th Ave
A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and a built-in oven.

19. 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.
$259 nightly
The price is $284
Oct 7 - Oct 8
Total with taxes and fees
Steps From The Snook Inn, Olde Marco
A white house with a metal roof, surrounded by a well-maintained lawn and a gravel path leading to a seating area with white chairs.

20. The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.

The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
Old Naples
10.0 out of 10, Exceptional, (22 reviews)
"This place had everything we needed with a great location , "
United States
terry s.
$757 nightly
The price is $831
Oct 28 - Oct 29
Total with taxes and fees
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
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

Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

10/10 Excellent
"Me sorprendio lo nuevo que esta el hotel. La decoracion lindisima, las camas y muebles de primera calidas. Todo lo que comi riquisimo. La verdad es que muy buena experiencia"
Bianca 1-night trip
Posted less than an hour ago
Compass by Margaritaville 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 $141 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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