Book Holiday Homes in Naples

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Featured Holiday Homes in Naples

NEW LISTING! Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning

NEW LISTING! Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning

2 out of 5
Bridgton
Located in Bridgton (West Bridgton), this vacation home is within a 5-minute drive of Moose Pond and Shawnee Peak.
NEW LISTING! Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning
Secluded, dog-friendly home near pond with private hot tub, huge deck, & firepit

Secluded, dog-friendly home near pond with private hot tub, huge deck, & firepit

Sweden
Located in Harrison, this vacation home is within a 15-minute drive of Highland Lake and Stearns Pond.
Secluded, dog-friendly home near pond with private hot tub, huge deck, & firepit
Luxurious,  4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine

Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine

Bridgton
With a stay at this vacation home in Bridgton, you'll be on the waterfront, just steps from Long Lake and a 4-minute drive from Deertrees Theatre and Cultural ...
Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine
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Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Poland
Located in Poland, Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views is on the waterfront, a 1-minute drive from Thompson Lake and ...
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
☼ Maine Lakefront Getaway ☼

☼ Maine Lakefront Getaway ☼

New Gloucester
Located in New Gloucester, this vacation home is on the waterfront, a 1-minute drive from Sabbathday Lake and 7 minutes from Poland Spring Preservation Society ...
☼ Maine Lakefront Getaway ☼
Modern, Luxury Lakefront Home on Crescent Lake, Maine

Modern, Luxury Lakefront Home on Crescent Lake, Maine

Raymond
Located in Raymond, this vacation home is on the waterfront, a 1-minute drive from Crescent Lake and 8 minutes from Panther Pond.
Modern, Luxury Lakefront Home on Crescent Lake, Maine
NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!

NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!

Casco
Located in Raymond, this vacation home is on the waterfront, a 1-minute drive from Crescent Lake and 7 minutes from Raymond Pond.
NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!
Family & pet friendly lakeside home with game room, close to park & pools

Family & pet friendly lakeside home with game room, close to park & pools

Lake Arrowhead
Located in Lake Arrowhead, this vacation home is within a 15-minute drive of Stratham Hill Farm Park and Woodland Valley Disc Golf.
Family & pet friendly lakeside home with game room, close to park & pools
Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

Auburn
With a stay at this vacation home in Auburn, you'll be within a 5-minute drive of Androscoggin River and Bonney Park.
Cozy Home Away From Home! Right Outside of the City! Dog Friendly!
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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.

Naples Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Naples vacation homes are the perfect way for you to wing it.

Holiday houses in Naples let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Naples in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Naples adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Naples with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Naples vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Naples Holiday Homes essential information

Accommodation
353 Holiday Homes
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Highest Price
Popular accommodation
NEW LISTING! Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning, Secluded, dog-friendly home near pond with private hot tub, huge deck, & firepit, Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine, Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views, ☼ Maine Lakefront Getaway ☼, Modern, Luxury Lakefront Home on Crescent Lake, Maine, NICEST LAKEHOUSE IN MAINE -- PRIVATE BEACH -- LUXURY!, Family & pet friendly lakeside home with game room, close to park & pools, Cozy Home Away From Home! Right Outside of the City! Dog Friendly!

Top trending hotels in Naples

fall foliage time

Book it now

Enjoy Trickey pond

fall foliage time Book it now Enjoy Trickey pond

Naples
A stay at this cabin places you in the heart of Naples, within a 5-minute walk of Trickey Pond and Sebago Cove.
fall foliage time Book it now Enjoy Trickey pond
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

Naples
When you stay at this cottage in Naples, you'll be on the waterfront, within a 5-minute drive of Brandy Pond and Songo River.
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Relax & Recharge this Fall! Tranquil Family-Owned, Sebago Lake Area, Pets free

Relax & Recharge this Fall! Tranquil Family-Owned, Sebago Lake Area, Pets free

Naples
When you stay at this cottage in Naples, you'll be on the waterfront, within a 5-minute drive of Brandy Pond and Songo River.
Relax & Recharge this Fall! Tranquil Family-Owned, Sebago Lake Area, Pets free
Save an average of 15% on thousands of hotels when you're signed in
Great Place for a Family Retreat! Sleeps 10

Great Place for a Family Retreat! Sleeps 10

Naples
With a stay at this vacation home in Naples, you'll be just steps from Sebago Lake State Park and Sebago Lake.
Great Place for a Family Retreat! Sleeps 10
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See all available properties in Naples
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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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^Subject to availability and chosen travel dates.