Holiday rentals in Naples

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars6 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.83 out of 5 average rating, 114 reviews

Home in Conway

A Large Vacation Home with hot tub, game room +

DeirdreRating, 5 stars2 months ago

Beautiful spacious home for a large group. Beds were very comfortable and we all had a great time in the game room and hot tub. Very convenient location. Note: there are very few kitchen basics- remember to pack trash bags, cleaning products, paper towels, plastic wrap, cooking oil, etc

4.98 out of 5 average rating, 54 reviews

Home in Jackson

The Sommet-Magical Views- Main house+Guest cottage

ChrisRating, 5 stars2 months ago

We loved the views at the Sommet. The house was spacious enough for all 6 of us without even spending much time in the guest house. We found the beds comfortable and the 3 bathrooms were helpful. The kitchen was pretty well stocked and we ended up eating in 5 out of 7 nights. The Uno, Jenga and Clue were big hits with the whole family. Thanks!

4.85 out of 5 average rating, 350 reviews

Home in Conway

Private In Village, HotTub, 1 bedroom, Fire Place

IsaacRating, 5 stars1 week ago

Perfect place for a weekend getaway for my wife and I. The house is comfortable and cozy to hang out at, we loved the fireplace in the living room and of course the hot tub! Quiet and secluded property while still only a 5-10 min walk to a ton of great shops/restaurants. We loved it!

5 out of 5 average rating, 6 reviews

Home in Harrison

2BR Lake House on Private Beach w/hot tub & sauna

JasonRating, 5 stars6 months ago

This is place is a gem. The lake is beautiful and the beach is very private. The house has a nice layout and is both spacious and cozy. This was our second year staying here and we plan to come back again! Dina is very responsive and great to work with.

4.85 out of 5 average rating, 105 reviews

Townhouse in Bartlett

Spacious Family Vaca Storyland*Saco*Close to all!

JoanneRating, 5 stars2 months ago

Great place to stay. The basement space for the kids is great, they each had their own bedroom but could hang in the common space. Golden Tee was a HIT! Centrally loacated to multiple ski mountains. Plenty of room to spread out and get comfortable!

Townhouse in Old Orchard Beach

4.89 out of 5 average rating, 9 reviews

Unit 3 Getaway - Perfect for Families!

DanielleRating, 5 stars8 months ago

Perfect size for our family of 4. Location to the beach was a short walk across the street. Kitchen was modern and clean. The beds were comfortable. Pillows were available to use but we brought ours from home. Two bathrooms are always a plus with two teenage girls, only request from them was a full length mirror in the 2nd bedroom to check out their outfits. Owner reached out during our stay to check in and see if everything was going well. Very thoughtful. Would highly recommend a stay here.

5 out of 5 average rating, 62 reviews

Home in Bethel

Dream Vacation Home - Full Amenities & Hot Tub

KatlynRating, 5 stars1 month ago

Group of mid 30 something’s stayed here for a long ski weekend! Plenty of space for us to spread out! Did a lot more hanging around the house than initially planned thanks to uncooperative weather, but there was plenty of games/puzzles in the house for us to use!

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Naples holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Naples's top sights

Point Sebago6 locals recommend

Sebago Lake State Park91 locals recommend

Bridgton Twin Drive-In76 locals recommend

Songo River Queen II55 locals recommend

Gary's Olde Towne Tavern48 locals recommend

Campfire Grille41 locals recommend

Other great holiday rentals in Naples

4.93 out of 5 average rating, 58 reviews

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

Elizabeth AnnRating, 5 stars1 week ago

The home was beautiful and matched the photos online. Clean and inviting! Gregory was responsive while booking and during our stay. Very kind and would stay here again for another girls weekend get away!

4.82 out of 5 average rating, 96 reviews

Home in Tamworth

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

ShaunaRating, 5 stars2 months ago

The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.

5 out of 5 average rating, 22 reviews

Flat in Bartlett

Large Family Apartment

KarenRating, 5 stars1 month ago

Kevin's place was great! Very clean, comfortable and in good area as we stayed for a week of skiing. Easy to get to Attitash ski resort and quick drive to Wildcat Mountain. Kevin was easy to communicate with and would return again next year for sure!

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars3 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

4.92 out of 5 average rating, 179 reviews

Cabin in Bartlett

Mountain View Retreat, Near skiing, shopping

JaimeRating, 5 stars3 months ago

We absolutely loved our stay! Plenty of room for 8 guests (and more!!) in a beautiful setting. There was many helpful amenities, like kitchen items, and plenty of towels. The location is perfectly centered to many popular things to do. James was always very responsive to questions left clear instructions. We highly recommend staying here and hope to do so again in the future.

Home in Old Orchard Beach

4.98 out of 5 average rating, 89 reviews

Woods Lane Golf and Beach Vacation

MarjorieRating, 5 stars7 months ago

Our group of 5 adults were so pleased we chose to stay at Jason’s house in Old Orchard Beach. We first looked at places in Portland, but Jason’s spacious house offered a quieter setting, with parking and more amenities, at a better price. Comfortable beds, immaculate throughout. Very thoughtfully appointed, with nightstands on both sides of the beds, and superior blackout blinds in the bedrooms. And we ended up spending less time in Old Port, because we enjoyed exploring the towns south of Portland: Old Orchard Beach, Saco, Biddeford, and we found good restaurants (including Holy Donuts!) nearby. We had no issues: we contacted Jason to confirmed our arrival/departure and he responded within minutes. We highly recommend!

4.9 out of 5 average rating, 94 reviews

Home in Freedom

Our Mountain Retreat – Lake Ossipee Access

FinRating, 5 stars1 month ago

Paula’s was the perfect spot for a weekend trip with a group of friends for my birthday! It had plenty of sleeping spots for us and was very comfortable, and we really loved the hot tub. They were such responsive and communicative hosts as well, and offered us a flexible late check-out. Thank you!