Holiday Homes in Naples

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Featured Holiday Homes in Naples

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
Property grounds
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
10.0 out of 10, Exceptional, (3)
"House was great, location was perfect and the local property manager was very responsive and helpful. "
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
☼ Maine Lakefront Getaway ☼
Outdoor dining
☼ Maine Lakefront Getaway ☼
9.6 out of 10, Exceptional, (62)
"We had a lovely stay! The house was just right and the lake was beautiful "
☼ Maine Lakefront Getaway ☼
Gorgeous home w/private hot tub, wood stove, firepit - near lake, skiing, hiking
Fridge, microwave, oven, stovetop
Gorgeous home w/private hot tub, wood stove, firepit - near lake, skiing, hiking
9.0 out of 10, Wonderful, (30)
"Very cozy home with a lovely master bedroom a nice outdoor hot tub."
Gorgeous home w/private hot tub, wood stove, firepit - near lake, skiing, hiking
Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons
Pool
Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons
10.0 out of 10, Exceptional, (20)
"We had a great time during our week at Highland Lake. The property was just what we were looking for. The host was great to work with, quickly answering all our questions. The lake and area are beautiful."
Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons
Tranquil cottage near beach with private dock, spacious patio & modern comforts
View from property
Tranquil cottage near beach with private dock, spacious patio & modern comforts
9.6 out of 10, Exceptional, (12)
"It was a good experience overall, other than a couple of guys inspecting the back of the property one morning. And we had yard work happening one morning. Later that week, both of the entrances to the cottage were being paved while we were out, and we had no way back to the property . All in all it was an ok experience."
Tranquil cottage near beach with private dock, spacious patio & modern comforts
Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine
Beach nearby, sun-loungers
Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine
10.0 out of 10, Exceptional, (42)
"Our third stay at this property."
Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine
Lovely home on Crystal Lake with private dock, lake views, deck, & grill
TV, fireplace
Lovely home on Crystal Lake with private dock, lake views, deck, & grill
9.2 out of 10, Wonderful, (23)
"This is an ideal location for a fun getaway for any season. Plenty of room for a large/extended family. While there is a road between the house and lake it didn’t detract from the experience at all. Pro tip, in cooler seasons turn on the ceiling fans to push the warmer air down. Otherwise the main room will feel cold. The dock is slightly off level and a couple doors don’t latch completely but those are just signs of a well loved camp."
Lovely home on Crystal Lake with private dock, lake views, deck, & grill
6 bedroom waterfront cabin -enjoy beautiful sunsets!
Smart TV, books, stereo
6 bedroom waterfront cabin -enjoy beautiful sunsets!
9.8 out of 10, Exceptional, (16)
"We had a great stay in this house. Enough space for everyone and we loved the open concept livingroom/kitchen area. The sunsets over the mountains are gorgeous! What a great spot on Frye Island. We will definitely be back!"
6 bedroom waterfront cabin -enjoy beautiful sunsets!
Lakefront House
Dining
Lakefront House
10.0 out of 10, Exceptional, (20)
"Amazing property. Lakeside view and quiet neighborhood, except for a few loons! Beautiful and comfortably appointed for a weekend away. Hot tub was a big hit and nights by the fires were just what we needed at the end of each day. "
The price is AU$1,615
includes taxes & fees
1 Oct - 2 Oct
Lakefront House
Serenity on Sebago Lake
View from property
Serenity on Sebago Lake
10.0 out of 10, Exceptional, (31)
"My family and I were lucky enough to book this house last minute before the summer ended. The location on the lake was incredible, the house was so warm and comfortable, and the kitchen was fully stocked (we love to cook somewhat elaborate meals). We were 8 adults and 2 pre-teens and everyone left thrilled with our experience. The two boys couldn’t get enough of the paddle boards and the game room. "
Serenity on Sebago Lake
Rise & Shine on Sebago Lake
Fridge, microwave, oven, stovetop
Rise & Shine on Sebago Lake
9.8 out of 10, Exceptional, (8)
"We wanted a place for extended family to be together for a family wedding at Caswell Farms There was room for everyone and a wonderful Lake Sebago view from multiple rooms We enjoyed kayaking, hot tub, wonderful kitchen amenities for a lobster boil Conveniently located to stores and restaurants Wonderful home and memories made!! Attentive hosts and maintenance staff Loved it!"
Rise & Shine on Sebago Lake
Views of the Sunrise from the Deck; Beach, Ski, snowmobile@The Water's Edge
Exterior
Views of the Sunrise from the Deck; Beach, Ski, snowmobile@The Water's Edge
10.0 out of 10, Exceptional, (15)
"This house was perfect for our larger group! The lake was amazing and the house had plenty of space for all of us. We had everything we needed at the house and had an amazing week!"
The price is AU$1,961
includes taxes & fees
30 Sept - 1 Oct
Views of the Sunrise from the Deck; Beach, Ski, snowmobile@The Water's Edge
"Loon Cottage" on Sand Pond
Property grounds
"Loon Cottage" on Sand Pond
10.0 out of 10, Exceptional, (3)
"The cabin was very clean when we arrived. The beds were very comfortable. The cabin has everything you need including many things in the kitchen to make meals if you want to. Towels, sheets, blankets, and swim towels were also provided. We enjoyed using the paddle boards and paddle boats. The pond was great for swimming and boating. The cabin has windows on all sides so we enjoyed lots of fresh air. It was also very quiet, restful, and peaceful on the pond. "
"Loon Cottage" on Sand Pond
Point Sebago Gated Golf & Beach Community
Fridge, microwave, oven, stovetop
Point Sebago Gated Golf & Beach Community
10.0 out of 10, Exceptional, (3)
"The house was clean and well appointed. We would definitely stay here again!"
Point Sebago Gated Golf & Beach Community
Spacious Lakefront home on Moose Pond
Exterior
Spacious Lakefront home on Moose Pond
10.0 out of 10, Exceptional, (13)
"Rare eastern shore of Moose pond cottage complete with dock, sandy beach, fire pit. House super clean. Plenty of room for family. Large kitchen makes it easy to cook while you enjoy the views. Big deck right on the lake. For our family this home has it all. The wonderful hosts even allow dogs! Thanks for much for giving us time at your family’s lake front cottage. Hope to return! "
Spacious Lakefront home on Moose Pond
NEW LISTING! Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning
Fridge, microwave, oven, dishwasher
NEW LISTING! Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning
2.0 star property
NEW LISTING! Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning
WATERFRONT ON LONG LAKE
Exterior
WATERFRONT ON LONG LAKE
10.0 out of 10, Exceptional, (8)
"The Deck House was a great spot for our family vacation this year. We had a large group of adults + 1 baby and there was plenty of room to spread out. The kitchen was perfect for cooking large meals with two fridges and a large range/oven. Lots of space for yard games and great fishing and kayaking spot. Everything was clean and beds were very comfortable. "
WATERFRONT ON LONG LAKE
Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!
Sun-loungers, beach towels
Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!
10.0 out of 10, Exceptional, (90)
"Great stay! Fantastic house for big group of family! We were in the area for a wedding nearby, and it was perfect for us. Would consider again for a family get together when the weather is warmer and enjoy the beach and the lake!"
Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!
Lakefront, dog-friendly home with dock, kayaks, SUPs, canoe, huge deck & firepit
Fridge, microwave, oven, stovetop
Lakefront, dog-friendly home with dock, kayaks, SUPs, canoe, huge deck & firepit
9.2 out of 10, Wonderful, (20)
"This house was perfect for a two night Brothers weekend. The house lived up to the pictures and it’s in a beautiful spot. House was clean. It wasn’t a dealbreaker, but there was a sulfur smell while taking a shower. It could probably use a better water filtering/softening system."
Lakefront, dog-friendly home with dock, kayaks, SUPs, canoe, huge deck & firepit
Beautiful Farmhouse located on 1200 acres of private bliss with a quiet pond.
Property grounds
Beautiful Farmhouse located on 1200 acres of private bliss with a quiet pond.
10.0 out of 10, Exceptional, (160)
"Retired ladies annual “Girls weekend” Already planning for next year. Best time ever"
Beautiful Farmhouse located on 1200 acres of private bliss with a quiet pond.
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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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Other property types in Naples

Blueberry season ? Book it now Enjoy Trickey pond
Exterior
Blueberry season ? Book it now Enjoy Trickey pond
10.0 out of 10, Exceptional, (285)
"This was our 2nd stay, celebrating another anniversary and once again it did not disappoint. We were able to enjoy 4 glorious days/nights in what we have truly come to think of as a little piece of heaven on earth. This year we did everything and nothing all at the same time... Lounging on the dock, naps in the hammock, grilling steaks, kayaking with the loons, floating in the beautiful water, fishing, having fires. And we got to do it all in the peace and solitude of this quiet little cabin,...
Blueberry season ? Book it now Enjoy Trickey pond
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
3 bedrooms, iron/ironing board, free WiFi
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
10.0 out of 10, Exceptional, (134)
"From the time I booked throughout the whole stay, the owner was very responsive and helpful . Had information at the house that helped with the stay and gave us great places to see , things to do and places to eat . The home was beautiful , was right on the water . Would definitely recommend to others ! "
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
Beach
Relax & Recharge this Fall! Tranquil Family-Owned, Sebago Lake Area, Pets free
9.8 out of 10, Exceptional, (110)
"The location is beautiful and peaceful and within the vicinity of a variety of fun attractions. The cabin was nice, clean, and well furnished. Kyle really went above and beyond accommodating us during our stay. He provided a lot of helpful information, not only about the property itself, but the surrounding area. He clearly communicated everything and gave us advance notice if he needed to visit the property for any reason, such as maintenance work. I cannot recommend this property enough. "
Relax & Recharge this Fall! Tranquil Family-Owned, Sebago Lake Area, Pets free
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.