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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Keewaydin Island vacation homes

A covered porch with a wooden ceiling, string lights, a ceiling fan, wicker furniture, and a view of greenery outside.

1. Cypress Cove

Cypress Cove
Naples
10.0 out of 10, Exceptional, (16 reviews)
"This was a wonderful place to stay, clean, spacious with a beautiful yard!"
United States
Rebecca L.
The price is ￥23,155
￥67,433 total
includes taxes & fees
Sep 25 - Sep 26
Cypress Cove
A wooden deck with wicker furniture, a grill, and a surfboard.

2. 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, (19 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 ￥32,878
￥64,527 total
includes taxes & fees
Sep 23 - Sep 24
Boaters Bayshore Bungalow on a Canal with Gulf Access
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
The price is ￥17,974
￥63,484 total
includes taxes & fees
Oct 4 - Oct 5
Noel Real Estate
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and an oven.

4. Boaters Bayshore Bungalow II w/Hot Tub. Bring Your Boat! Canal with Gulf Access!

Boaters Bayshore Bungalow II w/Hot Tub. Bring Your Boat! Canal with Gulf Access!
East Naples
9.8 out of 10, Exceptional, (6 reviews)
"Great host, property and location!"
United States
Stella A.
The price is ￥47,036
￥82,130 total
includes taxes & fees
Sep 23 - Sep 24
Boaters Bayshore Bungalow II w/Hot Tub. Bring Your Boat! Canal with Gulf Access!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. Blue Banyan Boathouse w/POOL/DOCK!

Blue Banyan Boathouse w/POOL/DOCK!
East Naples
9.4 out of 10, Exceptional, (11 reviews)
"lovely location and house."
United States
Basiliki
The price is ￥37,181
￥73,196 total
includes taxes & fees
Oct 4 - Oct 5
Blue Banyan Boathouse w/POOL/DOCK!
A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

6. 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 ￥42,474
￥89,604 total
includes taxes & fees
Oct 4 - Oct 5
The Paradise
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

7. Close to the Beach and 5th Ave! Fun Naples Peaceful Getaway 4U!

Close to the Beach and 5th Ave! Fun Naples Peaceful Getaway 4U!
Central Naples
10.0 out of 10, Exceptional, (12 reviews)
"Nice spot close to downtown and perfect space for our family. Good communication with host and a couple of minor issues were handled quickly and efficiently. Will recommend for others looking for an easy stay in Naples."
United States
David F.
The price is ￥22,023
￥62,326 total
includes taxes & fees
Sep 27 - Sep 28
Close to the Beach and 5th Ave! Fun Naples Peaceful Getaway 4U!
A living room with a TV, sofa, and coffee table, a ceiling fan, and a view of a swimming pool.

8. Peaceful Lakeview 3BR. Heated Pool Retreat.

Peaceful Lakeview 3BR. Heated Pool Retreat.
Naples
10.0 out of 10, Exceptional, (3 reviews)
"This was such a great place! The pool was beautiful and just the right temp, neighborhood was quiet and friendly, kitchen well stocked with dishes etc. I would stay again."
United States
Diane G.
The price is ￥36,867
￥81,052 total
includes taxes & fees
Sep 29 - Sep 30
Peaceful Lakeview 3BR. Heated Pool Retreat.
A pond with lily pads surrounded by palm trees and tropical vegetation.

9. Naples Art District

Naples Art District
East Naples
9.6 out of 10, Exceptional, (9 reviews)
"The place was very clean. The location was excellent. There are many restaurants and parks around this area. I would stay again."
United States
Kim C.
The price is ￥22,794
￥67,618 total
includes taxes & fees
Sep 23 - Sep 24
Naples Art District
A compact kitchen with a central island, bar stools, a dining table, and a microwave.

10. 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 ￥16,989
￥40,567 total
includes taxes & fees
Oct 1 - Oct 2
2/1 Hidden Gem
An outdoor seating area with Adirondack chairs, a central fire pit, and a pool in the background.

11. Tropical Oaks Estate | 3.8 Acres • 40' Pool + Spa

Tropical Oaks Estate | 3.8 Acres • 40' Pool + Spa
Central Naples
10.0 out of 10, Exceptional, (63 reviews)
"Stunning property which is perfectly located for beaches, shops etc in Naples. House is stocked with all appliances that you could possibly need. The house is probably the best maintained rental property I have stayed in with a fantastic pool."
United States
Mark C.
The price is ￥80,503
￥169,710 total
includes taxes & fees
Oct 9 - Oct 10
Tropical Oaks Estate | 3.8 Acres • 40' Pool + Spa
A covered outdoor deck with lounge chairs, a hot tub, and a view of a garden and buildings.

12. Green Turtle Boathouse/HOT TUB view of the canal

Green Turtle Boathouse/HOT TUB view of the canal
East Naples
The price is ￥30,675
￥65,732 total
includes taxes & fees
Sep 23 - Sep 24
Green Turtle Boathouse/HOT TUB view of the canal
A modern living room with a beige sofa, a round wooden coffee table, and a large window overlooking a swimming pool.

13. 6 Bedroom Two Villas, Heated Pool 2mil to Downtown

6 Bedroom Two Villas, Heated Pool 2mil to Downtown
East Naples
10.0 out of 10, Exceptional, (14 reviews)
"Great place to stay!"
United States
Marie W.
The price is ￥39,721
￥114,881 total
includes taxes & fees
Sep 27 - Sep 28
6 Bedroom Two Villas, Heated Pool 2mil to Downtown
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with a sink.

14. 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, (24 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 ￥35,392
￥81,714 total
includes taxes & fees
Sep 28 - Sep 29
Estey Oasis. Heated Pool! Close to Beaches/5th Ave!
A patio with four chairs and a small table, a window with blinds, and a garden with various plants.

15. Coastal Naples Park Getaway - Garden Grill Beach Nearby

Coastal Naples Park Getaway - Garden Grill Beach Nearby
2.0 star property
Naples Park
The price is ￥42,636
￥128,212 total
includes taxes & fees
Sep 23 - Sep 24
Coastal Naples Park Getaway - Garden Grill Beach Nearby
A spacious living room with a white sofa, a fluffy ottoman, and a fireplace.

16. Spacious Family Retreat with Pool Gym Sauna Pickleball and Guest Suite SLEEPS 16

Spacious Family Retreat with Pool Gym Sauna Pickleball and Guest Suite SLEEPS 16
Oakes Estates
10.0 out of 10, Exceptional, (22 reviews)
"Amazing!!! So many amenities"
United States
Ella P.
The price is ￥141,192
￥252,263 total
includes taxes & fees
Sep 25 - Sep 26
Spacious Family Retreat with Pool Gym Sauna Pickleball and Guest Suite SLEEPS 16
A breakfast table with a variety of fruits, cheese, and crackers, accompanied by wine glasses, set against a backdrop of a large window overlooking a garden.

17. 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, (15 reviews)
"The listing was exactly as described, with spacious rooms and plenty of space to relax. We loved that it truly felt like a home away from home. The property was thoughtfully stocked with everything we could possibly need and more, including games, kitchen equipment, and all the necessary utensils. The location was perfect. Just a short drive from our favorite restaurant, L’Appetito, and very close to our favorite beach for watching sunsets, Delnor-Wiggins Pass State Park. We had a wonderful stay...
United States
Ashley W.
The price is ￥20,387
￥102,772 total
includes taxes & fees
Sep 23 - Sep 24
Naples Retreat, Game Room + Pool, Table & Darts, Fenced Yard, Pet Friendly
A swimming pool with lounge chairs, a covered patio area, and a view of the surrounding landscape.

18. Family Tropical 4BR Oasis Pool Near Naples Beach

Family Tropical 4BR Oasis Pool Near Naples Beach
East Naples
9.8 out of 10, Exceptional, (6 reviews)
"Thoroughly enjoyed"
United States
Gwynn D.
The price is ￥24,489
￥80,633 total
includes taxes & fees
Oct 4 - Oct 5
Family Tropical 4BR Oasis Pool Near Naples Beach
A modern kitchen with a central island, a dining area, and a large sliding glass door leading to an outdoor patio.

19. ` 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
The price is ￥15,731
￥47,508 total
includes taxes & fees
Oct 5 - Oct 6
` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation
A covered outdoor area with a pool, seating, and a view of the surrounding landscape.

20. 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, (25 reviews)
"Beautiful home and great host!"
United States
Zachary P.
The price is ￥49,474
￥185,530 total
includes taxes & fees
Sep 23 - Sep 24
2023 New Construction! Beautiful Marco Island located around great amenities!
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

JW Marriott Marco Island Beach Resort

JW Marriott Marco Island Beach Resort

10/10 Excellent
"it was a nice time"
Ashley 3-night trip
Posted less than an hour ago
JW Marriott Marco Island Beach Resort

Find out more about Keewaydin Island

Keewaydin Island Vacation Homes information

Number of reviews
271
Accommodation
1059 Vacation Homes
Lowest Price
￥40,567
Highest Price
￥252,263

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