Chestnut Hill Rentals

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10,082 Houses

Resort Villa on Beach with Private Pool & Staff

Punta de Mita villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$2,050

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Price per night from

$228

Stunning Home at Paradise Palms Resort

Kissimmee house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$550

Recently Renovated Beautiful Beachfront Condo

New Smyrna Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Ocean front property” Very nice property. Very clean. Feels like you're at home. I would recommend this property to anyone. Beautiful setting

Responds fast! avg. 2 hours 15 minutes

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$206

Contemporary Golf Course Home

La Quinta house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$516

Your Disney Davenport Getaway!

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 6 minutes

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$138

Condo 1236 at Ventana Vista

Tucson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$243

BEST BEACH OCEANFRONT VIEWS! 5-STAR AMENITIES! Rated #1 Travel review SPECIALS!!

Orange Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

“Wonderful beach condo with amazing ocean views” I stayed at Audrey and Eric's condo during Hangout Music Fest, and it was a comfortable place to sleep, eat, get work done, and enjoy the view of the ocean. Checking in and out was hassle-free, as was communicating with the owners. Definitely a great spot for anyone looking to enjoy some time on the beach.

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$572

Slice of Paradise at Hampton Beach, NH

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$269

Condo 1179 at Ventana Vista

Tucson house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“This is a home away from home” We must like this condo since we have rented it for the past several years! Ventana Vista is private and, when we have been there(February), very quiet. The property is nicely located near Sabino Canyon and has good access to shopping and other Tucson activities. There is a pool and fitness room, too. We have found Tucson Vacation Rentals' service to be excellent - the check-in procedure is convenient and the condo is clean, well stocked and very well maintained. The facilities(laundry, kitchen, internet, TV) are up to date and in great working order. The furnishings are tasteful and very comfortable, as well. In short, this is a splendid base for a Tucson visit.

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$157

Villa 128 at Montecristo Estates in Cabo

Cabo San Lucas villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$745

Condo 1111 at Ventana Vista

Tucson house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$228

FLAGSTONE VILLA

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$361

Condo 2138 at Ventana Vista

Tucson condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$228

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$1,799

Panoramic Ocean and River View (daytona beach)

Daytona Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Our stay was great!” We can not complain! We thoroughly enjoyed our room! The location was great! Our week was wonderful. We can't wait to visit again!

Responds fast! avg. 59 minutes

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$218

Luxury 3-bdr house next to Disney

Kissimmee townhouse

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$195

Amura 1. Luxury 3 bedroom 2 bath Vacation rental

La Cruz de Huanacaxtle apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Great views from both balconys” We enjoyed our stay. The swimming pool at the complex and the beach club were spectacular. The walk back from the beach club was the hardest as it was a long uphill climd to the condo.

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Price per night from

$224

"Always Summertime at the Beach"

Marina del Rey apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$327

Dis Oasis Villa at Windsor Palms Resort - Close to Disney!

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

“Wonderful house for a large family group” The beds were comfortable, the house was immaculate and our needs were taken care of instantly by the owner. Close to shopping, restaurants and Disney World parks.

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Price per night from

$400

The French Suite in Las Vegas Tropical Luxury Home

Las Vegas private room

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$338

Jaco's Best Luxury and Value Condo

Jaco apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Best Vacation Ever” This was the perfect condo for our best vacation ever. We came as three couples and each couple had its own private room, bathroom and balcony. The design of the condo allows for a huge great room were we all gathered to discuss our daily events. The owner arranged to have his own private limo/guide pick us up from the airport. He also arrange free pedicures and manicures as well as nail art from a local Spa. It was the best my nails have ever looked in my entire life. When we arrived at the condo we were in awe of the beautiful condo and the breath taking views of the pacific ocean. The condo has an 20 foot mural of the ocean that you see when you first enter the unit. Your eyes then go from the mural to the most beautiful ocean view that my husband and I have ever seen. This unit was immaculately clean and decorated with luxury sculptures. The mattresses and linens were best we have ever slept on in all of our years of travel. During the mornings we would walk the beach, then each afternoon we did a local trip of either Zip-Linning, Fishing, ATV, or hiking. Then in the late afternoon the ladies went to the private pool as the men worked out in the private work out room. At night we went to some fabulous restaurants that the owner recommended and got a discount for us. Two nights we went out dancing to early in the morning. One thing we never missed was the sunsets from the balcony. The view from his balcony was spectacular. I would highly recommend you staying at this condo. We are coming back next year and this is the only place we will stay.

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$670

Sunsets, Cocktails and Memories!

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Spacious and beautiful” My girlfriends and I just finished our stay for the third year in a row. This is an outstanding condo. With four or five of us, there is plenty of room. The private spiral staircase to the beach is great! No waiting for the elevator with everyone else. We love sitting on the porch early in the morning and again at sunset. Spectacular views! Also you can visit the Suncoast Seabird Sanctuary which is about 1/2 block to the south. Would highly recommend this condo. We hope to be back again next year.

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$382

Stunning 5 Bed/3bath with Pool/Spa + Games Room

Kissimmee villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$218

“Wonderful holiday” We had a lovely holiday staying at Emerald magic, the villa was just right for our family of 12 , our 5 grandsons loved the south facing swimming pool which was always lovely and warm while we enjoyed relaxing on the 6 sunbeds. The games room had loads of things to keep them happy and occupied while the adults relaxed. The barbecue with free gas was great at mealtimes, although it was out of gas when we arrived it was very quickly replaced with one phone call as were any other problems which occurred, excellent service. Plenty of pool towels, saving packing our own and the double buggy was so handy at the parks. The location to disney parks could not be better, only about 10 minutes drive and the complex is lovely with a really friendly lady at reception. Also Thank you for the special touch of the rose on the bed which made celebrating our ruby wedding anniversary a special occasion.

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$430

Luxurious Resort Condos minutes from Disney World with full access to all

Celebration condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 8 minutes

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$103

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$516

Platinum 3 BR +Loft BR Ski-in-out Mountain Retreat

Avon townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$573

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$1,145

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$985

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$229

BRUTAL COLD: POLAR VORTEX RETURNS! 2 1/2 BR, 3 BA, FLEE THE SNOW! BEACH WARM UP!

Puerto Vallarta apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Very satisfied” Really enjoyed our stay. Excellent service and the condo was very nice. It was our third year in a row at Icon Vallarta amd we will be back, for sre in the future.

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$516

“Beautiful spacious home in a quiet Gated Community.” We were in Florida for the National Pop Warner Football finals. I was able to rent this home on short notice (one week) and was pleasantly surprised it was beautifully maintained and well stocked. Sri was very accommodating and easy to reach. We had several children with us of various ages and they were all kept occupied in the game room. Pool never really got warm but we did read the literature and wasn't expecting bath water but the pool and spa at the clubhouse was comfortable. Had a great time and would definitely rent again great value for your money. Also is very close to all the attractions just a short drive to any park you plan to visit.

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Price per night from

$430

VIDA Vacation Resort

Nuevo Nayarit house

  • 2 bedrooms
  • 7 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$436

“Large enough for the whole family” We had a great stay and were really pleased with the size of the house. It allowed members of our extended family to have privacy but of course the family room, kitchen, and media/game room were the most popular areas. The kids and grand kids enjoyed the pool. The weather was unseasonably cold but we paid to heat the pool and everyone seemed surprised and pleased that is was so comfortably warm. Sri is very easy to work with and responded super fast to email communication. This is definitely the way to go when you have a large family. Very reasonably priced for the space and accommodations.

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$430

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$430

Monsenor P-1

Playa de Cura apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$142

Lake Berkley Holiday Villa with FREE pool heating.

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated) Private outdoor pool (heated)

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Price per night from

$170

Viewing 38 of 10,082
rentals in Chestnut Hill

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