Keewaydin Island Vacation Rentals

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Our top choices for Keewaydin Island vacation rentals

Marriott's Crystal Shores

Marriott's Crystal Shores
3.5 star property
South End
9.2 out of 10, Wonderful, (225)
"Beautiful property "
United States
Rose
$1,050 nightly
The price is $1,166
Jan 9 - Jan 10
Total with taxes and fees
Marriott's Crystal Shores

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2228)
"Clean, good amenities. Good services. Gym is fairly good with all the equipment you need. Restaurant is lovely, high quality and delicious. Pool area also clean and service is great. "
United Kingdom
Debbie
$542 nightly
The price is $602
Jan 31 - Feb 1
Total with taxes and fees
Bellasera Resort

Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (245)
"Room was very clean, staff was awesome, and the location was perfect. I will definitely stay here again."
United States
Tamisha
$194 nightly
The price is $215
Jan 8 - Jan 9
Total with taxes and fees
Wiggins Pass Chalet

GreenLinks Golf Villas at Lely Resort

GreenLinks Golf Villas at Lely Resort
3.0 star property
Naples
9.4 out of 10, Exceptional, (544)
"Clean and staff was helpful. Beautiful views"
United States
Rebecca
$343 nightly
The price is $370
Jan 4 - Jan 5
Total with taxes and fees
GreenLinks Golf Villas at Lely Resort

Cozy Apartment in Naples

Cozy Apartment in Naples
Rural Estates
9.2 out of 10, Wonderful, (15)
"The place was off the grid from the busyness of the downtown/beach area but close enough to go there and the other areas too! "
United States
Robyn S.
$277 nightly
The price is $287
Jan 5 - Jan 6
Total with taxes and fees
Cozy Apartment in Naples

Nuevo y Confortable Estudio

Nuevo y Confortable Estudio
Naples
9.6 out of 10, Exceptional, (9)
"Great stay for a solo trip! This location was very close to the beaches and pickleball courts. Definitely recommend this place! "
United States
Esosa
$140 nightly
The price is $153
Jan 16 - Jan 17
Total with taxes and fees
Nuevo y Confortable Estudio

2/1 Hidden Gem

2/1 Hidden Gem
Naples
9.8 out of 10, Exceptional, (16)
"It was so relaxing and close to everything, really enjoyed the stay ! "
United States
janice G.
$250 nightly
The price is $274
Jan 6 - Jan 7
Total with taxes and fees
2/1 Hidden Gem

Tiny Home Renovated 2023 1.5 Mi, 2 Beach Kit W & D Regular Bed on Imperial River

Tiny Home Renovated 2023 1.5 Mi, 2 Beach Kit W & D Regular Bed on Imperial River
Bonita Shores
9.8 out of 10, Exceptional, (6)
"Cute little home! Enjoyed our stay. Thank you for your hospitality "
United States
Robin S.
$214 nightly
The price is $236
Jan 5 - Jan 6
Total with taxes and fees
Tiny Home Renovated 2023 1.5 Mi, 2 Beach Kit W & D Regular Bed on Imperial River

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

Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!
East Naples
9.0 out of 10, Wonderful, (18)
"Great location and perfect spot for my quick work trip "
United States
Anastasia A.
$308 nightly
The price is $339
Jan 12 - Jan 13
Total with taxes and fees
Quiet Naples Home: Walking Distance to Downtown. Pet Friendly!

Amazing Private Suite Large Bathroom 3.3mi to Beach Close 2 Everything Updated

Amazing Private Suite Large Bathroom 3.3mi to Beach Close 2 Everything Updated
Bonita Shores
9.8 out of 10, Exceptional, (13)
"Excellent place to stay. "
United States
Barb
$186 nightly
The price is $205
Jan 12 - Jan 13
Total with taxes and fees
Amazing Private Suite Large Bathroom 3.3mi to Beach Close 2 Everything Updated

2 Villas, Pickleball/Basketball, Resort style heated pool/Hot tub, Naples escape

2 Villas, Pickleball/Basketball, Resort style heated pool/Hot tub, Naples escape
Naples
10.0 out of 10, Exceptional, (15)
"Great home and the pool is wonderful"
United States
Daryl M.
$1,365 nightly
The price is $1,497
Jan 6 - Jan 7
Total with taxes and fees
2 Villas, Pickleball/Basketball, Resort style heated pool/Hot tub, Naples escape

Florida style home walking distance to Barefoot Beach

Florida style home walking distance to Barefoot Beach
Bonita Shores
9.0 out of 10, Wonderful, (27)
"Have stayed here several times over the last couple years so it truly feels like home when I arrive "
United States
Larry W.
$333 nightly
The price is $367
Jan 17 - Jan 18
Total with taxes and fees
Florida style home walking distance to Barefoot Beach

* * Endless Summer * * Beach, Unique & Comfort

* * Endless Summer * * Beach, Unique & Comfort
Naples Park
9.4 out of 10, Exceptional, (16)
"A beautiful property with attention to detail. Nice beach towels and beach chairs provided as well as bikes.Perfect location for beach time and many options for night life -- restaurants, shopping, cocktails.Would definitely recommend this place for your next getaway."
United States
Terry W.
$314 nightly
The price is $330
Jan 4 - Jan 5
Total with taxes and fees
* * Endless Summer * * Beach, Unique & Comfort

House w/ Heated Pool & Grill - Walk to Beach!

House w/ Heated Pool & Grill - Walk to Beach!
3.0 star property
South End
$640 nightly
The price is $707
Jan 22 - Jan 23
Total with taxes and fees
House w/ Heated Pool & Grill - Walk to Beach!

Gulf Access Canal & Dock 1.2 Miles 2 Beach Just Redone Close 2 Barefoot Beach!!!

Gulf Access Canal & Dock 1.2 Miles 2 Beach Just Redone Close 2 Barefoot Beach!!!
Bonita Shores
10.0 out of 10, Exceptional, (12)
"Great property and very nicely nestled in Bonita! "
United States
Paul K.
$294 nightly
The price is $324
Jan 11 - Jan 12
Total with taxes and fees
Gulf Access Canal & Dock 1.2 Miles 2 Beach Just Redone Close 2 Barefoot Beach!!!

Naples Retreat, Game Room + Pool, Table & Darts, Fenced Yard, Pet Friendly

Naples Retreat, Game Room + Pool, Table & Darts, Fenced Yard, Pet Friendly
Palm River Estates
10.0 out of 10, Exceptional, (11)
"We loved the time we spent and go to play at great golf course in the area! Would definitely come back again!"
United States
William R.
$629 nightly
The price is $690
Jan 4 - Jan 5
Total with taxes and fees
Naples Retreat, Game Room + Pool, Table & Darts, Fenced Yard, Pet Friendly

Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River

Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
Bonita Shores
9.6 out of 10, Exceptional, (4)
"Is good , and Beauty"
United States
Jorge T.
$229 nightly
The price is $252
Jan 5 - Jan 6
Total with taxes and fees
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River

85" TV•World Tennis Club•Beach 4mi•Sauna•2 Heated Pools•Hot Tub•Pickleball

85" TV•World Tennis Club•Beach 4mi•Sauna•2 Heated Pools•Hot Tub•Pickleball
2.0 star property
Central Naples
10.0 out of 10, Exceptional, (2)
"Liked this condo. Very well furnished. Funny story looked for a frying pan and didn't immediately fine one. Later opened the oven and it was packed with frying pans! Large TV and other amenities, very nice condo!"
United States
Brian S.
$740 nightly
The price is $812
Jan 6 - Jan 7
Total with taxes and fees
85" TV•World Tennis Club•Beach 4mi•Sauna•2 Heated Pools•Hot Tub•Pickleball

1 Bedroom House with Hot Tub

1 Bedroom House with Hot Tub
Naples Park
9.6 out of 10, Exceptional, (20)
"Very enjoyable trip!"
United States
Sumari P.
$342 nightly
The price is $376
Jan 12 - Jan 13
Total with taxes and fees
1 Bedroom House with Hot Tub

Luxury Waterfront Villa with Heated Pool, Private Dock, Kayaks, & Fishing Gear

Luxury Waterfront Villa with Heated Pool, Private Dock, Kayaks, & Fishing Gear
3.0 star property
Marco Island
10.0 out of 10, Exceptional, (14)
""We had a wonderful stay! The place was clean, comfortable, and exactly as described. The host was very kind and attentive. Highly recommend!""
United States
Lianet
$1,044 nightly
The price is $1,146
Jan 6 - Jan 7
Total with taxes and fees
Luxury Waterfront Villa with Heated Pool, Private Dock, Kayaks, & Fishing Gear
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

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 $215 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.