A coastal landscape with a sandy beach, clear turquoise waters, and a network of small islands.

Keewaydin Island Holiday Rentals

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Our top choices for Keewaydin Island holiday rentals

1. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,328 reviews)
"The perfect place for a family vacation"
United States
Lorenzo
The price is AU$396
includes taxes & fees
23 Sept - 24 Sept
Bellasera Resort

2. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (285 reviews)
"Overall it was an awesome stay."
United States
Patricio
The price is AU$152
includes taxes & fees
21 Sept - 22 Sept
Wiggins Pass Chalet

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
The price is AU$559
includes taxes & fees
9 Sept - 10 Sept
Noel Real Estate

4. Free Golf Until Oct! Naples Condo w/ Resort Pool

Free Golf Until Oct! Naples Condo w/ Resort Pool
3.5 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 AU$560
includes taxes & fees
3 Sept - 4 Sept
Free Golf Until Oct! Naples Condo w/ Resort Pool

5. Blue Banyan Boathouse w/POOL/DOCK!

Blue Banyan Boathouse w/POOL/DOCK!
East Naples
9.2 out of 10, Wonderful, (9 reviews)
"lovely location and house."
United States
Basiliki
The price is AU$647
includes taxes & fees
5 Sept - 6 Sept
Blue Banyan Boathouse w/POOL/DOCK!

6. 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)
"We had a great time! The location was amazing…a few steps to the beach and a few to downtown in the other direction. The place and beds were comfortable and it was well-stocked! Will come again!"
United States
Sheila N.
The price is AU$816
includes taxes & fees
2 Sept - 3 Sept
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

7. 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, (207 reviews)
"Perfect location. Thanks for the beach chairs, umbrellas and cart. Wouldn't have been able to enjoy the beach without them!"
United States
Vicki H.
The price is AU$907
includes taxes & fees
15 Sept - 16 Sept
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt

8. Boaters Bayshore Bungalow on a Canal with Gulf Access

Boaters Bayshore Bungalow on a Canal with Gulf Access
East Naples
9.6 out of 10, Exceptional, (18 reviews)
"We had a great time at this lovely bungalow. It was cozy, spotlessly clean, and the patio was a wonderful bonus. Highly recommend this property for a relaxing stay."
United States
Katarina O.
The price is AU$560
includes taxes & fees
7 Sept - 8 Sept
Boaters Bayshore Bungalow on a Canal with Gulf Access

9. ` 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 traveller
The price is AU$440
includes taxes & fees
2 Sept - 3 Sept
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

10. Marriott's Crystal Shores

Marriott's Crystal Shores
3.5 star property
South End
9.2 out of 10, Wonderful, (235 reviews)
"Excellent experience , staff very kind, facilities very clean. We really enjoy our stay! Good job!!!"
United States
KELERYN M
The price is AU$881
includes taxes & fees
8 Sept - 9 Sept
Marriott's Crystal Shores

11. 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.
The price is AU$553
includes taxes & fees
2 Sept - 3 Sept
Free Golf Until Oct! Naples Condo w/ Resort Pool

12. 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)
"The property was beautiful and perfect for our week in Florida. The condo is spacious and clean with all the essentials supplied. The pool was very close and very relaxing. We loved staying here and hope to return in the future."
United States
Anonymous traveller
The price is AU$584
includes taxes & fees
14 Sept - 15 Sept
Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

13. The Paradise

The Paradise
East Naples
10.0 out of 10, Exceptional, (14 reviews)
"Our hosts were quickly responsive to any concerns we had. Their home is gorgeous, comfortable, conveniently situated, and modern. "
United States
Michelle L.
The price is AU$799
includes taxes & fees
2 Sept - 3 Sept
The Paradise

14. ` The Bohemian Heaven ` w/ SPA, 2miles to downtown

` The Bohemian Heaven ` w/ SPA, 2miles to downtown
East Naples
9.8 out of 10, Exceptional, (17 reviews)
"We would stay here again."
United States
Shane L.
The price is AU$396
includes taxes & fees
2 Sept - 3 Sept
` The Bohemian Heaven ` w/ SPA, 2miles to downtown

15. Overlooking 10th Fairway 2 Free Rounds of Golf

Overlooking 10th Fairway 2 Free Rounds of Golf
3.5 star property
Naples
The price is AU$782
includes taxes & fees
11 Sept - 12 Sept
Overlooking 10th Fairway 2 Free Rounds of Golf

16. 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.
The price is AU$345
includes taxes & fees
2 Sept - 3 Sept
2/1 Hidden Gem

17. 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
The price is AU$399
includes taxes & fees
2 Sept - 3 Sept
The Gulfstream Place 2

18. Amazing Olde Marco Condo, Sunsets & Dolphins

Amazing Olde Marco Condo, Sunsets & Dolphins
Olde Marco
9.8 out of 10, Exceptional, (56 reviews)
"This condo was perfect! It’s in a quiet area right on the canal. However, many things to do/places to eat & drink within minutes. The condo is beautiful inside and very well maintained. Really enjoyed sitting on the balcony and watching the nature around there. Highly recommend this place!"
United States
Michelle
The price is AU$480
includes taxes & fees
2 Sept - 3 Sept
Amazing Olde Marco Condo, Sunsets & Dolphins

19. Nuevo y Confortable Estudio

Nuevo y Confortable Estudio
Naples
8.6 out of 10, Excellent, (14 reviews)
"The place was easy to find and directions were very clear."
United States
Laura C.
The price is AU$217
includes taxes & fees
11 Sept - 12 Sept
Nuevo y Confortable Estudio

20. 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, (23 reviews)
"Beautiful home and had all the perfect accommodations for beach/pool and children! Definitely recommend for a family outing !"
United States
Rolando
The price is AU$722
includes taxes & fees
8 Sept - 9 Sept
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

Find out more about Keewaydin Island

Everything you need to know about Keewaydin Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Keewaydin Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Keewaydin Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Keewaydin Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Keewaydin Island holiday rentals we have selected for you start as low as AU$152 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Keewaydin Island rentals

At Expedia, we put the best Keewaydin Island holiday 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 holiday.

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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