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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Keewaydin Island vacation rentals

Lobby

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,298 reviews)
"We love this place!"
United States
isis
$285 nightly
The price is $317
Jul 29 - Jul 30
Total with taxes and fees
Bellasera Resort
Outdoor pool, a heated pool

Swimming pool, lake view, minutes to Naple's downtown and beach.

Swimming pool, lake view, minutes to Naple's downtown and beach.
East Naples
9.2 out of 10, Wonderful, (51 reviews)
"Pool and view was lovely"
United States
Nancy C.
$170 nightly
The price is $187
Jul 20 - Jul 21
Total with taxes and fees
Swimming pool, lake view, minutes to Naple's downtown and beach.
Property entrance

Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (279 reviews)
"The girl on the front desk, when I’ve arrived omg she’s was really nice and excellent customer service I was visiting another places to stay and never someone was very nice like her. 5 stars for her; and the hotel really clean I love it"
United States
Tania
$111 nightly
The price is $124
Jul 25 - Jul 26
Total with taxes and fees
Wiggins Pass Chalet
Apartment, Patio, Garden View | Private kitchen

Noel Real Estate

Noel Real Estate
2.0 star property
East Naples
9.4 out of 10, Exceptional, (3 reviews)
"Property was easy to find and just as described and listed. very home-feeling and comfortable. "
United States
Lauren
$373 nightly
The price is $414
Jul 20 - Jul 21
Total with taxes and fees
Noel Real Estate
Aerial view

Bologna - Luxury 2-BR Condo with Lake & Golf Views at Green Links, Lely Resort. Access to Pool, Hot Tub, Tennis Courts, and Golf Courses. Near Naples Beaches & Downtown

Bologna - Luxury 2-BR Condo with Lake & Golf Views at Green Links, Lely Resort. Access to Pool, Hot Tub, Tennis Courts, and Golf Courses. Near Naples Beaches & Downtown
3.5 star property
Naples
9.4 out of 10, Exceptional, (3 reviews)
"The pool is fantastic. The room was clean, though there were minor glitches with the plumbing. "
United States
LuWayne
$617 nightly
The price is $685
Jul 21 - Jul 22
Total with taxes and fees
Bologna - Luxury 2-BR Condo with Lake & Golf Views at Green Links, Lely Resort. Access to Pool, Hot Tub, Tennis Courts, and Golf Courses. Near Naples Beaches & Downtown
Terrace/patio

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

"The Coastal Dream" only 3miles to the beach.
East Naples
9.8 out of 10, Exceptional, (23 reviews)
"Nice home, worked well for our short golf getaway."
United States
John B.
$293 nightly
The price is $303
Jul 26 - Jul 27
Total with taxes and fees
"The Coastal Dream" only 3miles to the beach.
Beach nearby, sun loungers, beach towels

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, (204 reviews)
"Location was perfect and condo was so clean and had everything we needed to enjoy a beach getaway. Judy was so attentive in checking in and making recommendations as it was our first trip to Naples. Now we see why people love it there and will definitely book this unit again!"
United States
Kimberly A.
$606 nightly
The price is $665
Jul 27 - Jul 28
Total with taxes and fees
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
Terrace/patio

Cypress Cove

Cypress Cove
Naples
10.0 out of 10, Exceptional, (15 reviews)
"This was a wonderful place to stay, clean, spacious with a beautiful yard!"
United States
Rebecca L.
$377 nightly
The price is $414
Jul 20 - Jul 21
Total with taxes and fees
Cypress Cove
Pool

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
Jul 26 - Jul 27
Total with taxes and fees
Free Golf Until Oct! Naples Condo w/ Resort Pool
Coffee/tea maker, fridge, microwave, oven

Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!

Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
East Naples
9.2 out of 10, Wonderful, (25 reviews)
"Great location! House was clean and inviting."
United States
Jane C.
$233 nightly
The price is $256
Jul 26 - Jul 27
Total with taxes and fees
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
Beach nearby

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, (41 reviews)
"Great location, clean rooms. "
United States
Inna Z.
$554 nightly
The price is $608
Aug 8 - Aug 9
Total with taxes and fees
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
Sun loungers, beach towels

ONE BLOCK to the beach, Restaurants & Shopping!!!

ONE BLOCK to the beach, Restaurants & Shopping!!!
Old Naples
10.0 out of 10, Exceptional, (53 reviews)
"The location was perfect and our hosts were so helpful and welcoming!"
United States
Theresa J.
$417 nightly
The price is $458
Jul 26 - Jul 27
Total with taxes and fees
ONE BLOCK to the beach, Restaurants & Shopping!!!
Interior

THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches

THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches
East Naples
10.0 out of 10, Exceptional, (34 reviews)
"The house was clean and the check in was very easy. The pool was perfect! The chairs were comfortable and the yard was very private. "
United States
Lisa S.
$519 nightly
The price is $570
Jul 26 - Jul 27
Total with taxes and fees
THE TERRACOTTA, Heated Pool! Close to 5th Ave and Beaches
Exterior

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)
"Our stay was wonderful! The apartment was beautiful and so clean. The area was amazing and we absolutely enjoyed everything about this place. "
United States
Samantha L.
$360 nightly
The price is $396
Aug 19 - Aug 20
Total with taxes and fees
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches
Aerial view

Genoa Vacation Rental: Stylish 2-BR Condo with Golf & Lake Views. Resort-Style Pool, Hot Tub, and Easy Access to Championship Golf. Minutes from Naples Beaches, 5th Avenue S, and Marco Island

Genoa Vacation Rental: Stylish 2-BR Condo with Golf & Lake Views. Resort-Style Pool, Hot Tub, and Easy Access to Championship Golf. Minutes from Naples Beaches, 5th Avenue S, and Marco Island
3.5 star property
Naples
10.0 out of 10, Exceptional, (1 review)
"Pool was very nice "
United States
britney
$810 nightly
The price is $899
Jul 20 - Jul 21
Total with taxes and fees
Genoa Vacation Rental: Stylish 2-BR Condo with Golf & Lake Views. Resort-Style Pool, Hot Tub, and Easy Access to Championship Golf. Minutes from Naples Beaches, 5th Avenue S, and Marco Island
Outdoor dining

Amazing Olde Marco Condo, Sunsets & Dolphins

Amazing Olde Marco Condo, Sunsets & Dolphins
Olde Marco
9.8 out of 10, Exceptional, (53 reviews)
"Great place!!!!"
United States
Peyton S.
$302 nightly
The price is $332
Jul 24 - Jul 25
Total with taxes and fees
Amazing Olde Marco Condo, Sunsets & Dolphins
House, Multiple Beds | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

Milano Vacation Rental: Newly Renovated 3-BR Home with Private Pool, Hot Tub, and Pet-Friendly Front Yard. Minutes from Vanderbilt Beach

Milano Vacation Rental: Newly Renovated 3-BR Home with Private Pool, Hot Tub, and Pet-Friendly Front Yard. Minutes from Vanderbilt Beach
3.5 star property
Naples Park
8.0 out of 10, Very Good, (5 reviews)
"This home is beautifully maintained in a quiet neighborhood just blocks away from the waterway. Spacious and clean with a nice pool and comfortable rooms. "
United States
Mandolin
$1,041 nightly
The price is $1,156
Jul 21 - Jul 22
Total with taxes and fees
Milano Vacation Rental: Newly Renovated 3-BR Home with Private Pool, Hot Tub, and Pet-Friendly Front Yard. Minutes from Vanderbilt Beach
Exterior

Margaritaville, Steps From The Snook Inn, Olde Marco

Margaritaville, Steps From The Snook Inn, Olde Marco
Olde Marco
9.4 out of 10, Exceptional, (60 reviews)
"Enjoyed our time there, will book again. "
United States
Frank W.
$287 nightly
The price is $315
Jul 26 - Jul 27
Total with taxes and fees
Margaritaville, Steps From The Snook Inn, Olde Marco
Terrace/patio

Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.

Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.
Old Naples
9.8 out of 10, Exceptional, (37 reviews)
"Enjoyed our stay. Clean, stylish, conveniently located to the beach, stores and restaurants. "
United States
Andrew R.
$442 nightly
The price is $485
Aug 10 - Aug 11
Total with taxes and fees
Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.
Coffee/tea maker, fridge, microwave, oven

Estey Oasis. Heated Pool! Close to Beaches/5th Ave!

Estey Oasis. Heated Pool! Close to Beaches/5th Ave!
East Naples
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful home and had all the perfect accommodations for beach/pool and children! Definitely recommend for a family outing !"
United States
Rolando
$471 nightly
The price is $517
Aug 16 - Aug 17
Total with taxes and fees
Estey Oasis. Heated Pool! Close to Beaches/5th Ave!
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

AC Hotel by Marriott Naples 5th Avenue

AC Hotel by Marriott Naples 5th Avenue

10/10 Excellent
"The staff on front desk were very friendly and helpful, we only stayed one night but it was a great location to 5th street and really lovely hotel"
Andrew 1-night trip
Posted 16 hours ago
AC Hotel by Marriott 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 $122 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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