Keewaydin Island Vacation Rentals from CA $127: Short-Term Rentals for 2026

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Our top choices for Keewaydin Island vacation rentals

A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

1. Noel Real Estate

East Naples

Lauren

CA $575 total

includes taxes & fees

Dec 1 - Dec 2

A cozy living room with a grey sofa, a small table, and chairs. There is a window with curtains, a lamp, and a mirror on the wall.

2. King Bed Near Pickleball, Beach & Downtown

East Naples

Francois S.

CA $331 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, wooden stools, and a sliding glass door leading to a patio.

3. `The Boho Bliss` - Reset & Recharge Wellness House

East Naples

Nancy S.

CA $401 total

includes taxes & fees

Nov 8 - Nov 9

A spacious, multi-level interior with a grand staircase, elegant chandeliers, and a luxurious seating area.

4. Bellasera Resort

Old Naples

vasilisa

CA $542 total

includes taxes & fees

Nov 16 - Nov 17

An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

5. Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

East Naples

Andrew F.

CA $464 total

includes taxes & fees

Nov 22 - Nov 23

An indoor pool area with a glass floor, seating around the pool, and a bar area with a blue ceiling and hanging lights.

6. Park Shore Resort

Park Shore

nathaly

CA $331 total

includes taxes & fees

Nov 8 - Nov 9

A white pergola with a brick pathway leading to a house.

7. Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.

Old Naples

Andrew R.

CA $871 total

includes taxes & fees

Nov 30 - Dec 1

A modern bathroom with a glass shower enclosure, a wooden vanity with a round mirror, and a tiled backsplash.

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

East Naples

Robert K.

CA $928 total

includes taxes & fees

Nov 21 - Nov 22

A clear blue pool with a stone feature, surrounded by palm trees and lounge chairs.

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

Naples

Colleen V.

CA $521 total

includes taxes & fees

Nov 8 - Nov 9

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

Naples

Mark

CA $562 total

includes taxes & fees

Nov 12 - Nov 13

A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and a built-in oven.

11. Steps From The Snook Inn, Olde Marco

Olde Marco

Lucyna R.

CA $384 total

includes taxes & fees

Nov 12 - Nov 13

A compact kitchen with a central island, bar stools, a dining table, and a microwave.

12. 2/1 Hidden Gem

Naples

Katherine S.

CA $315 total

includes taxes & fees

Nov 9 - Nov 10

A covered outdoor area with a view of a river, docked boats, and a chair with a table.

13. Amazing Olde Marco Condo, Sunsets & Dolphins

Olde Marco

Michelle

CA $431 total

includes taxes & fees

Nov 8 - Nov 9

A coastal hotel with a central courtyard, a swimming pool, and a marina.

14. Margaritaville, Steps From The Snook Inn, Olde Marco

Olde Marco

Frannie L.

CA $417 total

includes taxes & fees

Nov 8 - Nov 9

A beach with clear skies, palm trees, and calm waves.

15. Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

Central Naples

Fred K.

CA $543 total

includes taxes & fees

Nov 19 - Nov 20

A resort with a swimming pool, palm trees, and a view of the water.

16. Water View of Marco Pass, Heated Pool & Marina-Newly Updated 5th Floor 1Br/1Ba

Olde Marco

Andrew H.

CA $415 total

includes taxes & fees

Nov 11 - Nov 12

A beach with a variety of seashells and a view of the ocean with waves.

17. Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)

Marco Island

Maite

CA $589 total

includes taxes & fees

Nov 16 - Nov 17

A covered outdoor deck with lounge chairs, a hot tub, and a view of a garden and buildings.

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

East Naples

Heidi

CA $653 total

includes taxes & fees

Nov 8 - Nov 9

An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

19. Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

Old Naples

Robert W.

CA $920 total

includes taxes & fees

Nov 13 - Nov 14

A modern living room with a sofa, coffee table, and a TV. There is a kitchen area with a bar and stools.

20. THE TERRANOVA, Heated Pool, 10 Min to 5th Ave/Beach 5 min to US Open Pickleball

East Naples

Olga F.

CA $1,012 total

includes taxes & fees

Nov 10 - Nov 11

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Top Keewaydin Island Hotel Reviews

A modern dining area with wicker furniture and a glass partition wall.

Hampton Inn & Suites Naples South

East Naples

10/10 Excellent

Serge

A hotel lobby with seating areas, a large window with a view, and a carpeted floor.

Staybridge Suites Naples – Marco Island by IHG

Naples

10/10 Excellent

Heather

A hotel entrance with a covered walkway, palm trees, and a sign for 'CULTA INN & SUITES'.

La Quinta Inn & Suites by Wyndham Naples Downtown

East Naples

10/10 Excellent

Herman

A modern hotel lobby with a dining area, seating arrangements, and large potted plants.

AC Hotel by Marriott Naples 5th Avenue

Redevelopment Area

10/10 Excellent

Ziad

A resort with a pool, lounge chairs, and a view of the marina.

Cove Inn on Naples Bay

Old Naples

10/10 Excellent

Don

A garden pathway with palm trees, red flowers, and a thatched-roof structure.

Marco Island Lakeside Inn

Marco Island

10/10 Excellent

Gail

Bellasera Resort

Old Naples

10/10 Excellent

Rob

A cozy outdoor seating area with a white bench and potted plants, a sign for 'Bijoux' gelateria, and a brick pathway.

Olde Marco Island Inn and Suites

Olde Marco

10/10 Excellent

Derek

A multi-story hotel with a covered entrance, palm trees, and a parking lot.

Fairfield Inn & Suites by Marriott Naples

Rural Estates

10/10 Excellent

David

A Holiday Inn Express hotel with a covered entrance, outdoor seating, and a well-lit facade.

Holiday Inn Express Naples South I-75 by IHG

Rural Estates

10/10 Excellent

Emile

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Keewaydin Island vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Keewaydin Island vacation rentals we have selected for you start as low as CA $127 per night. Entering your travel dates in the search wizard 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.

Keewaydin Island Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Keewaydin Island vacation rentals

1. Noel Real Estate

2. King Bed Near Pickleball, Beach & Downtown

3. `The Boho Bliss` - Reset & Recharge Wellness House

4. Bellasera Resort

5. Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

6. Park Shore Resort

7. Two Blocks to Gulf and Old Naples. A one bedroom cottage for work and play.

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

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

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

11. Steps From The Snook Inn, Olde Marco

12. 2/1 Hidden Gem

13. Amazing Olde Marco Condo, Sunsets & Dolphins

14. Margaritaville, Steps From The Snook Inn, Olde Marco

15. Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

16. Water View of Marco Pass, Heated Pool & Marina-Newly Updated 5th Floor 1Br/1Ba

17. Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)

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

19. Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

20. THE TERRANOVA, Heated Pool, 10 Min to 5th Ave/Beach 5 min to US Open Pickleball

Find vacation rentals that suit your style

Top Keewaydin Island Hotel Reviews

Hampton Inn & Suites Naples South

10/10 Excellent

Find out more about Keewaydin Island

Keewaydin Island vacation rentals: An excellent choice for every season

How to find incredible deals on Keewaydin Island rentals

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