Keewaydin Island Vacation Rentals from $125: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Keewaydin Island vacation rentals

1. Bellasera Resort

Old Naples

Rokney

$256 nightly

Aug 9 - Aug 10

Total with taxes and fees

Apartment, Patio, Garden View | Private kitchen

2. Noel Real Estate

East Naples

Lauren

$372 nightly

Aug 14 - Aug 15

Total with taxes and fees

3. Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

Naples

Anonymous traveler

$334 nightly

Aug 8 - Aug 9

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

4. ` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

East Naples

Anonymous traveler

$293 nightly

Aug 16 - Aug 17

Total with taxes and fees

5. Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.

Old Naples

Andrew R.

$431 nightly

Aug 10 - Aug 11

Total with taxes and fees

6. Swimming pool, lake view, minutes to Naple's downtown and beach.

East Naples

Anonymous traveler

$171 nightly

Aug 12 - Aug 13

Total with taxes and fees

7. "The Coastal Dream" only 3miles to the beach.

East Naples

John B.

$309 nightly

Aug 19 - Aug 20

Total with taxes and fees

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

Central Naples

Rick B.

$336 nightly

Sep 6 - Sep 7

Total with taxes and fees

9. Nuevo y Confortable Estudio

Naples

Laura C.

$140 nightly

Aug 7 - Aug 8

Total with taxes and fees

10. The Gulfstream Place 2

East Naples

Richard

$259 nightly

Aug 7 - Aug 8

Total with taxes and fees

11. Wiggins Pass Chalet

Naples

Tania

$113 nightly

Aug 7 - Aug 8

Total with taxes and fees

12. Greenlinks Luxury Condo, 3BD, ground floor, golf, pool

Naples

CANDI E.

$414 nightly

Aug 7 - Aug 8

Total with taxes and fees

13. Private Suite near the Beach

Naples Park

Nicole Y.

$120 nightly

Aug 9 - Aug 10

Total with taxes and fees

14. Centrally Located Boho Private BdR - 7 mi to beach

Naples

Vivek T.

$117 nightly

Aug 7 - Aug 8

Total with taxes and fees

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

Naples

James K.

$366 nightly

Aug 9 - Aug 10

Total with taxes and fees

16. 2/1 Hidden Gem

Naples

Katherine S.

$198 nightly

Aug 11 - Aug 12

Total with taxes and fees

17. Cypress Cove

Naples

Rebecca L.

$380 nightly

Aug 10 - Aug 11

Total with taxes and fees

18. Overlooking 10th Fairway 2 Free Rounds of Golf

Naples

$505 nightly

Aug 8 - Aug 9

Total with taxes and fees

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

Marco Island

Jeff K.

$374 nightly

Aug 12 - Aug 13

Total with taxes and fees

20. Cozy 2-bedroom house in tranquil Marco Island with AC

Marco Island

Brandon R.

$339 nightly

Aug 21 - Aug 22

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Private vacation homes

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Keewaydin Island Hotel Reviews

The Perry Hotel Naples

10/10 Excellent

"We would definitely book this hotel again!"

Hilton Marco Island Beach Resort and Spa

10/10 Excellent

"Conviently located across the street from multiple restaurants and ice cream parlor. Everything is within a 10 minute drive (breakfast spots, shopping souvenirs, supermarket and drug store/pharmacy). The property is well maintained and pristine. The rooms are modern and clean. Parking on site is available for $40 a night. The pool is clean and fun. The beach was behind the property and beautiful. Watersports are on site as well. The weather was great. The sun was strong, but at times the clouds covered it and then rained and then sun and then clouds. It was nice for people to get a break from the extreme sun. We have stayed here 2 times now with small children. Family oriented hotel. A++ The porters in the front are great and help with luggage and reccomendations. Showing appreciation goes a long way. Thanks to Eddie in front he was a great guy. Also thanks to Steve working the drinks and food by the pool area. Highly reccomend this hotel. Marco Island is a great place to dissappear to."

JW Marriott Marco Island Beach Resort

10/10 Excellent

"★★★★☆ We had a wonderful stay overall at the JW Marriott Marco Island. The resort is beautiful, the beach is stunning, and the amenities were excellent. My wife especially enjoyed her spa experience, and we had a fantastic birthday dinner at Ario. The staff we encountered were friendly, and our family created many wonderful memories during our stay. The only disappointment was the lack of recognition for my wife's birthday. I noted the special occasion when making the reservation and also mentioned it again in person at check-in. Unfortunately, there was no birthday card, welcome note, or even a simple acknowledgment from the hotel. For a luxury resort of this caliber, I expected at least a small gesture to make the occasion feel special. It wasn't about receiving an expensive gift—it was about the thoughtfulness and attention to detail that guests associate with a premium hospitality experience. Despite that, we truly enjoyed our stay and appreciate the beautiful property and the memories we made as a family. I hope the hotel improves its communication and guest recognition for special occasions in the future."

Naples Beach Club, A Four Seasons Resort

10/10 Excellent

"**⭐⭐⭐⭐⭐ A five-star experience — for our pet too!** Our stay at the Four Seasons Resort Naples was simply spectacular from start to finish. From check-in, we were welcomed with genuine warmth, and the attention to detail was felt in every corner: impeccable rooms, breathtaking views of the Gulf of Mexico, and service that anticipates every need before you even ask. What truly surprised us was how well they treated our dog. The staff asked for him by name, brought him water during our walks around the resort, and the "canine concierge" recommended nearby pet-friendly parks and areas. It was clear that for them, pets aren't just "tolerated" — they're genuinely welcomed and pampered. Between the spa, the exceptional restaurants, and the white sand beaches, every moment felt like a well-deserved luxury. Without a doubt, one of the best resorts we've ever stayed at, both for us and for our four-legged companion. We'll definitely be back!"

Beachfront Bliss: Charming 2-Bedroom South End Condo at Somerset Condominium

10/10 Excellent

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I would definitely stay here again, clean quiet, one thing is missing, a jacuzzi"

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 $125 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.

Keewaydin Island Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Keewaydin Island vacation rentals

1. Bellasera Resort

2. Noel Real Estate

3. Luxury GreenLinks Condo: Top Rated Golf, Resort Pool,LakeView - close to beaches

4. ` The Black Vanilla ` Luxe Retreat Sauna, Cold Plunge & Pure Relaxation

5. Location!!! A one bedroom cottage, 2 blocks from Gulf, and Old Naples.

6. Swimming pool, lake view, minutes to Naple's downtown and beach.

7. "The Coastal Dream" only 3miles to the beach.

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

9. Nuevo y Confortable Estudio

10. The Gulfstream Place 2

11. Wiggins Pass Chalet

12. Greenlinks Luxury Condo, 3BD, ground floor, golf, pool

13. Private Suite near the Beach

14. Centrally Located Boho Private BdR - 7 mi to beach

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

16. 2/1 Hidden Gem

17. Cypress Cove

18. Overlooking 10th Fairway 2 Free Rounds of Golf

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

20. Cozy 2-bedroom house in tranquil Marco Island with AC

Find vacation rentals that suit your style

Top Keewaydin Island Hotel Reviews

The Perry Hotel Naples

Find out more about Keewaydin Island

Explore a world of travel with Expedia

Expedia's Latest Trends

Go further with the Expedia app