Keewaydin Island Vacation Rentals

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Our top choices for Keewaydin Island vacation rentals

Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (274 reviews)
"This was in was in a great location! Everything was clean, staff was helpful and friendly. The wife and I will definitely book it again next time we’re in Naples!"
United States
Daniel Luis
The price is CA $174
CA $193 total
includes taxes & fees
Jun 2 - Jun 3
Wiggins Pass Chalet

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,275 reviews)
"Great accommodations , very clean and Great Service We will certainly return. "
United States
Phillip
The price is CA $339
CA $437 total
includes taxes & fees
Jun 9 - Jun 10
Bellasera Resort

Walk to Celebration Park: Naples Home w/ Pool!

Walk to Celebration Park: Naples Home w/ Pool!
3.0 star property
East Naples
10.0 out of 10, Exceptional, (2 reviews)
"The house was amazing & the location was great!!"
United States
Jennifer
The price is CA $486
CA $951 total
includes taxes & fees
Jun 17 - Jun 18
Walk to Celebration Park: Naples Home w/ Pool!

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
The price is CA $188
CA $591 total
includes taxes & fees
Jun 8 - Jun 9
Noel Real Estate

Marriott's Crystal Shores

Marriott's Crystal Shores
3.5 star property
South End
9.2 out of 10, Wonderful, (228 reviews)
"The property is amazing"
United States
Juan
The price is CA $1,281
CA $1,422 total
includes taxes & fees
Jun 3 - Jun 4
Marriott's Crystal Shores

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, (45 reviews)
"ImpeccableLovelyCozyQuietConvenient"
United States
valerie G.
The price is CA $207
CA $257 total
includes taxes & fees
Jun 2 - Jun 3
Swimming pool, lake view, minutes to Naple's downtown and beach.

Cozy Getaway!

Cozy Getaway!
Bonita Shores
9.6 out of 10, Exceptional, (37 reviews)
"Good response to any issues we had. Great location!"
United States
Sue S.
The price is CA $190
CA $516 total
includes taxes & fees
Jun 2 - Jun 3
Cozy Getaway!

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, (202 reviews)
"Good communication with the host, Helen was helpful and prompt in responding to our request, amenities were very nice"
United States
Donna W.
The price is CA $357
CA $888 total
includes taxes & fees
Jun 21 - Jun 22
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt

5-Star Luxury Condo - Pool – Near Bonita Springs Beach

5-Star Luxury Condo - Pool – Near Bonita Springs Beach
Bonita Shores
10.0 out of 10, Exceptional, (50 reviews)
"Wonderful stay at the beautiful and well stocked condo. The host was very responsive every time that I emailed with a question.The location is great, close to everything. It was so comfortable & beautifully decorated. I would highly recommend & we plan on returning again"
United States
Cean V.
The price is CA $186
CA $545 total
includes taxes & fees
Jun 3 - Jun 4
5-Star Luxury Condo - Pool – Near Bonita Springs Beach

Luxury Waterfront Villa with Heated Pool, Private Dock, Kayaks, Fire Pit

Luxury Waterfront Villa with Heated Pool, Private Dock, Kayaks, Fire Pit
Marco Island
10.0 out of 10, Exceptional, (21 reviews)
"Everything was fantastic!"
United States
Camden B.
The price is CA $672
CA $1,446 total
includes taxes & fees
Jun 2 - Jun 3
Luxury Waterfront Villa with Heated Pool, Private Dock, Kayaks, Fire Pit

Family Friendly Tigertail Beach Home Salt water Pool & Spa

Family Friendly Tigertail Beach Home Salt water Pool & Spa
Tigertail Beach
9.6 out of 10, Exceptional, (123 reviews)
"Great place and location. All amenities needed were available. Would go again!"
United States
Lindita A.
Family Friendly Tigertail Beach Home Salt water Pool & Spa

Special Spring Break Stay Home in Marco Island

Special Spring Break Stay Home in Marco Island
South End
10.0 out of 10, Exceptional, (22 reviews)
"Great location, clean, spacious house. Perfect for a Marco island getaway!"
United States
Mike D.
Special Spring Break Stay Home in Marco Island

Naples Condo w/ Golf View & Resort-style Amenities

Naples Condo w/ Golf View & Resort-style Amenities
3.0 star property
Naples
10.0 out of 10, Exceptional, (1 review)
"We spent a weekend here while visiting family in the area. Great location for us. Super friendly and helpful. Nice sunset view over the golf course. "
United States
Mark
The price is CA $222
CA $547 total
includes taxes & fees
Jun 2 - Jun 3
Naples Condo w/ Golf View & Resort-style Amenities

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, (35 reviews)
"Location was awesome."
United States
Jenna G.
The price is CA $261
CA $766 total
includes taxes & fees
Jul 2 - Jul 3
Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.

Amazing Olde Marco Condo, Sunsets & Dolphins

Amazing Olde Marco Condo, Sunsets & Dolphins
Olde Marco
9.6 out of 10, Exceptional, (50 reviews)
"Great place!!!!"
United States
Peyton S.
The price is CA $247
CA $495 total
includes taxes & fees
Jun 19 - Jun 20
Amazing Olde Marco Condo, Sunsets & Dolphins

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, (20 reviews)
"Really enjoyed this nicely decorated condo.. Very clean, spacious and well equipped. Communication was very good. Will definitely stay here again. "
United States
Mike D.
The price is CA $153
CA $535 total
includes taxes & fees
Jun 5 - Jun 6
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

Marco Island Florida Family Vacation Home-heated pool, beach, Pet friendly

Marco Island Florida Family Vacation Home-heated pool, beach, Pet friendly
Marco Island
9.8 out of 10, Exceptional, (40 reviews)
"Very clean property, conveniently located near public beach access and close to all restaurants."
United States
Anonymous traveller
The price is CA $248
CA $872 total
includes taxes & fees
Jun 17 - Jun 18
Marco Island Florida Family Vacation Home-heated pool, beach, Pet friendly

Naples Condo w/ Golf View & Resort-Style Amenities

Naples Condo w/ Golf View & Resort-Style Amenities
Naples
9.8 out of 10, Exceptional, (48 reviews)
"The unit was stocked with kitchen and bathroom supplies, the view from the patio was tranquil and Ray, the owner, was easily accessible. The property has a nice pool, walking trails and is well-located."
United States
AUGUST
The price is CA $199
CA $551 total
includes taxes & fees
Jun 2 - Jun 3
Naples Condo w/ Golf View & Resort-Style Amenities

2023 New Construction! Beautiful Marco Island located around great amenities!

2023 New Construction! Beautiful Marco Island located around great amenities!
Marco Island
10.0 out of 10, Exceptional, (22 reviews)
"We really enjoyed the house and the area! It was close to everything. We had some minor issues and it lacked some of the amenities found in other homes we have rented. The house should have a booklet outlining all requirements and instructions for the stay. "
United States
Martin H.
The price is CA $469
CA $1,691 total
includes taxes & fees
Jun 2 - Jun 3
2023 New Construction! Beautiful Marco Island located around great amenities!

Sunrise Waterfront Cottage

Sunrise Waterfront Cottage
Marco Island
10.0 out of 10, Exceptional, (47 reviews)
"Beautiful location on the water and nearby restaurants Bikes and kayaks available Our host was wonderful "
United States
Joseph W.
The price is CA $310
CA $602 total
includes taxes & fees
Jun 6 - Jun 7
Sunrise Waterfront Cottage
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Keewaydin Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.