A red building with an American flag, a dock with boats, and a forest in the background.

Naples Holiday Rentals

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Our top choices for Naples holiday rentals

1. LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Naples
9.8 out of 10, Exceptional, (9 reviews)
"Fantastic home! We had a great time here and look forward to booking again."
United States
Gina P.
The price is NZ$1,307
includes taxes & fees
15 Nov - 16 Nov
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

2. All Points’ End (HOUSE)

All Points’ End (HOUSE)
Naples
The price is NZ$632
includes taxes & fees
9 Dec - 10 Dec
All Points’ End (HOUSE)

3. Barn on Pleasant-walk to Highland beach & town

Barn on Pleasant-walk to Highland beach & town
Bridgton
10.0 out of 10, Exceptional, (29 reviews)
"Absolutely beautiful place to stay! The room was very welcoming and cozy. "
United States
Robyn N.
The price is NZ$353
includes taxes & fees
10 Nov - 11 Nov
Barn on Pleasant-walk to Highland beach & town

4. Casco Tiny house, and HOT TUB!

Casco Tiny house, and HOT TUB!
Casco
The price is NZ$503
includes taxes & fees
10 Nov - 11 Nov
Casco Tiny house, and HOT TUB!

5. Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn

Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn
Bridgton
10.0 out of 10, Exceptional, (73 reviews)
"Cabin is thoughtfully furnished and equipped.We enjoyed listening to the bird song in the mornings, while sitting on the dock."
United States
Peggy P.
The price is NZ$965
includes taxes & fees
10 Nov - 11 Nov
Closest Lakefront Log Cabin with Stunning Views & Expansive Private Lawn

6. Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
9.8 out of 10, Exceptional, (19 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is NZ$1,316
includes taxes & fees
10 Nov - 11 Nov
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

7. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake
Casco
10.0 out of 10, Exceptional, (2 reviews)
"Clean and tidy"
United States
Edward R.
The price is NZ$509
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

8. Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Bridgton
10.0 out of 10, Exceptional, (67 reviews)
"This was our second stay at Windsor Cottage, and it was just as wonderful as the first! The cottage is always spotless, beautifully furnished, and truly feels like a home away from home. We love the lake access, the pet-friendly accommodations, and being just minutes from downtown Bridgton. We can’t wait to come back again!"
United States
Cortney C.
The price is NZ$639
includes taxes & fees
11 Nov - 12 Nov
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

9. Relaxing A-Frame with Hot Tub and Lake Access

Relaxing A-Frame with Hot Tub and Lake Access
Denmark
10.0 out of 10, Exceptional, (5 reviews)
"Great house, we had a wonderful time!"
United States
Alex F.
The price is NZ$812
includes taxes & fees
10 Nov - 11 Nov
Relaxing A-Frame with Hot Tub and Lake Access

10. Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
9.2 out of 10, Wonderful, (5 reviews)
"The Manor Suite was cozy and charming. It was walking distance from restaurants and shops. I would have loved to stay longer to explore the area.I hope to stay there again if I return to Bridgton next summer."
United States
Jennifer
The price is NZ$311
includes taxes & fees
29 Nov - 30 Nov
Manor Suite,cozy newly renovated,downtown & beach

11. Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!

Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!
Bridgton
10.0 out of 10, Exceptional, (4 reviews)
"The house was clean and beautiful! The host made sure we had everything we needed including items for our doggie. We would definitely recommend staying here!"
United States
Jacqueline R.
The price is NZ$999
includes taxes & fees
10 Nov - 11 Nov
Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!

12. The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi

The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi
Bridgton
10.0 out of 10, Exceptional, (3 reviews)
"Host was amazing. Great spot in Bridgton!"
Canada
Joshua
The price is NZ$651
includes taxes & fees
10 Nov - 11 Nov
The Birch Retreat — Private Luxury Tiny Home in Bridgton, Maine with AC & WiFi

13. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is NZ$468
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom house with shared beach access to Sebago Lake

14. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
Newly Remodeled Cottage with AC- Sebago Lake Area

15. Winter Farmhouse - Hot Tub, Sauna & Ski Day Trips

Winter Farmhouse - Hot Tub, Sauna & Ski Day Trips
Harrison
The price is NZ$1,338
includes taxes & fees
16 Nov - 17 Nov
Winter Farmhouse - Hot Tub, Sauna & Ski Day Trips

16. EPIC VIEWS - Pond - Crooked River 14 ACRES - SECLUDED

EPIC VIEWS - Pond - Crooked River 14 ACRES - SECLUDED
Harrison
9.2 out of 10, Wonderful, (7 reviews)
"It felt like having a main lodge or cabin AND a 'campsite' down by the river. Enjoyed kayaking and canoeing. Perfect for what we needed, as far as lots of room for kids and dog to run around. Liked the decor inside, nice vibe. We were sad to leave."
United States
Alisa B.
The price is NZ$1,140
includes taxes & fees
10 Nov - 11 Nov
EPIC VIEWS - Pond - Crooked River 14 ACRES - SECLUDED

17. Ell Suite walk to town beach

Ell Suite walk to town beach
Bridgton
8.8 out of 10, Excellent, (3 reviews)
"Great spot as advertised "
United States
mark l.
The price is NZ$255
includes taxes & fees
18 Nov - 19 Nov
Ell Suite walk to town beach

18. THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (16 reviews)
"Had a wonderful overnight - was perfect weekend getaway. Was great being in nature!"
United States
Alex D.
The price is NZ$494
includes taxes & fees
10 Nov - 11 Nov
THE LILLIPAD.Off-grid A frame. Sebago lake region!

19. Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table

Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
Brownfield
10.0 out of 10, Exceptional, (6 reviews)
"Great little camp with lake access! Thanks for hosting us :-)"
United States
Anonymous traveller
The price is NZ$549
includes taxes & fees
16 Nov - 17 Nov
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table

20. Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass

Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Norway
9.8 out of 10, Exceptional, (12 reviews)
"Such a great and cozy few days away from reality, highly recommend this warm, home away from home kind of place!"
United States
Elizabeth S.
The price is NZ$1,298
includes taxes & fees
22 Nov - 23 Nov
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
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 Naples Hotel Reviews

Find out more about Naples

Everything you need to know about Naples 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 Naples 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 Naples holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Naples holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Naples. 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 Naples 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 Naples holiday rentals we have selected for you start as low as NZ$319 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Naples rentals

At Expedia, we put the best Naples 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 Naples 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 Naples 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 Naples. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Naples?

Yes, there are holiday rentals in Naples close to Steamboat Landing Mini Golf, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Naples. Make sure you have time to check out the parks and coffee shops during your trip.

What are some of the best holiday rentals that Naples has to offer?

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings: This holiday home rental outside of Naples is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and 1 hot tub.

How many holiday rentals are there in Naples?

With 70 Expedia holiday rentals, you're guaranteed to find just the right place for your Naples stay.

What’s there to see and do in Naples?

Brandy Pond and Long Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Steamboat Landing Mini Golf. Other places in town to visit include Sebago Lake State Park and Sebago Lake.

What’s a holiday rental in Naples like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Naples. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips.