Chestnut Hill Rentals

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10,747 Houses

5Br/3Ba townhome with hot tub/ lake View,Close Disney,Seaworld,Convention Center

Kissimmee townhouse

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Ok” Overall it was fine..checkout was at 11 and at 10 cleaners knocked on door and then preceded to sit in driveway waiting for us to leave. There was no dish soap or soap in bathrooms which would have been nice.

Responds fast! avg. 1 hour 27 minutes

Match: Children's pool Climbing frame

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Price per night from

$149

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Price per night from

$490

5br/3ba townhome with hot tub,Near Disney,Seaworld,Convention center

Kissimmee apartment

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Vacation rental” The overall experience was nice. The hot was only hot for one day and wouldn't get hot again there after. The cookware needs to be updated but overall we had a great time. I wouldn't definitely rent this rental again.

Responds fast! avg. 1 hour 27 minutes

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$138

From $110/nt,4br/3ba townhome with lake view,Near Disney,Seaworld

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$132

Capaes - Luxury 4 Bedroom Duplex with Pool - Sleeps 10

Santa Elena condo

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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$144

Farm Barcoiça

Ferreira do Zezere farmhouse

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

“where I'd like to spend my life !” quiet, clean, fantastic house, ideal for family with small children, away from everything. perfect for my idea of perfect vacation.

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Price per night from

$550

Reunion Resort-luxe 3BR/3BA Villa-Water Park

Reunion hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Terrific Property” Dear Stacy and Craig, What a time we had! Expecting, as many Orlando-travelers do, that the theme parks would be our only major attractions, we were so pleased to be able to add our accommodations to this list as well. The Sagers have made it absolutely impossible for their guests not to have a first-class time in their condo on the Reunion property. And what an amazing property it is! Swimming pools galore (to include my daughter and son's favorite water park with a lazy river) and my personal favorite swimming and late-afternoon beverage/snacking pool area, Seven Eagles. It is here that we were able to really let-down after an amusement park day and relax only to go home to Stacy and Craig's little slice of heaven with beds that beacon even the most restless tourists. I loved the beds! So incredibly comfy with just the perfect linens making vacationers want to stay in bed just a little longer before heading back out to Sea World; Animal Kingdom; the Magic Kingdom, and the the like (all of which are not more than 15 minutes away). A true place of luxury, the Reunion four star hotel is always available to the Sager's guests serving up pub and kid fare all day and night; fine dining; and late night cocktails and sushi on the 11th floor where fireworks from local theme parks are a daily occurrence. Will we go back, yes! In fact, we have already booked again with the Sagers so we can dream away some of those cold winter days and nights looking forward to our next tip down. Thanks to you both for a wonderful stay. Jen and Dan Smith

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Price per night from

$205

8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$344

AWESOME WHITEFISH TOWNHOUSE/Big Mountain/Glacier/3 bd/3 lvls/2 pools/GREAT HOSTS

Whitefish apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“A Forest Bungalow!” My family and I had a great time at Ptarmigan, Big Mountain-Whitefish, MT. We did it all! Went to Glacier National Park, enjoyed Big Mountain, toured the town and relaxed in the hottub! Our favorite part was making meals in a house in the woods. It was so magical being surrounded by cedar trees on a mountainside. Thanks for the memorable stay!

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$247

Making Waves

Surfside Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Making Waves” Very nice home. Perfect for 4 adults and 4 children. House was clean. Appliances were older, but all in good working condition. Main beds were comfortable. Grandson loved the bunk beds. Golf cart is always a plus and a “must” at Oceanside Villages for easy travel to the beach, pools and playground.

Responds fast! avg. 13 minutes

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$195

“Good price for family of 10” With 5 bedrooms, fits 10 comfortably. Owner is very helpful and location is 20mins from the parks. Walmart and restaurants are very close.

Responds fast! avg. 1 hour 27 minutes

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$149

⭐Comfy Villa w/ Golf Clubhouse - Adventure & Thrills For Everyone⭐

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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Price per night from

$336

Lake Travis The Hollows Largest 3BR/3BA Villa with Beautiful Lake Travis Views!

Jonestown apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$287

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$121

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Price per night from

$201

2-br watervu apt-Seawind onthe Bay,Montego Bay,Jam

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$212

Mountain Paradise Rancho Rio Alegre In Dominican Rep

Monsenor Nouel Province house

  • 17 bedrooms
  • 15 bathrooms
  • sleeps 40

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Price per night from

$1,374

Responds fast! avg. 1 hour 47 minutes

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Price per night from

$636

Vacaciones de invierno en la playa o con teletrabajo.

La Serena apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$103

Luxury 3 Bedroom Cottage, Pool&WiFi,Steps to Beach

Myrtle Beach cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Gulfstream” We had an amazing stay. The pool was very close to our front door. Jay was accommodating and quick to answer any questions we had.

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$195

9br/6ba pool villa from $380/nt,Close to Disney

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 20

“Nice house for large family” The house itself is very attractive. The bedrooms were very well appointed. There were sufficient towels and plates, silverware, glassware, etc., for our party. Our major problem was the parking. It is a very over-crowded community and we had five cars (to be expected in a six master-bedroom house that fits 18+), and we often had trouble parking near the house. My only other complaint (if you could call it that) was the trash. We had one large trash can and it got picked up on Monday morning. We were there for six full days with 13 people, so we easily refilled it up and then had multiple loose bags with nowhere to put them through the end of our stay. No recyclable can was available, either, so recyclables had to go in trash bags. Owner was easy to work with. Thanks for a very nice home!

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$401

Penthouse w Ocean, Mountain & Pool Views

Farallon apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$315

Williamsburg Deluxe Cabin

Williamsburg log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$273

Christmas Mountain Village - 3 Bedroom Unit

Wisconsin Dells log cabin

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$172

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Price per night from

$336

From $110/nt,Near Disney,Seaworld,Convention Center,4br/3ba townhome with hottub

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$132

5 bedroom Private Family Get Away

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,374

Charming house in the countryside

Milagro cottage

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$538

Responds fast! avg. 3 hours 5 minutes

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$381

“Perfect localtion and great house with a perfect pool.” I'm a rookie at time sharing, but the owner helped me all the way. We saved money by staying here instead of inside Disney. The location was only 10 to 15 minutes for all of the Parks.

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Price per night from

$1,030

Great Pocono vacation from the city noise

Bushkill house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$144

Comfy house in Playa del Carmen

Playa del Carmen house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$29

“A Classy Vacation Experience in any Season” My brother, who has problems walking, and I stayed at Sunnybank for a little under a week in the early spring when the Corolla horses are foaling. The layout of the well-appointed, three-storey main building was perfect for our needs: the fabulous view from the top floor living room provided the inspiration for him to walk up the grand stair case, and he could take the elevator when he was having problems walking. (There are two bedrooms with walk-in showers to accommodate people who have a problem walking.) It rained the first two days, which might have been gloomy any where else, but the library of videos, and stashes of games and playing cards gave us the opportunity to connect in ways that we hadn't since we were children. The fabulous cook's kitchen and multiple eating areas can accommodate a wedding party, family reunion, or any get away time one might want. Mine was a working vacation and the office there, which is outfitted with excellent Ethernet and WiFi connections plus a daybed for napping, was a better arrangement than my office at home. Comfort and casual, yet classy ambience abounds at Sunnybank. An excellent find!

Responds fast! avg. 3 hours 13 minutes

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$800

Off Season Mid Week $95 per couple / per night

Lake Geneva house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Super Friendly” Great folks running this place. They really give the home town experience with amenities of a major hotel. This property is right next to a beautiful lake. The options are great for either the relaxed weekend or if you want to water skiing or out on a boat to fish it is all there. Really pleased with vacation this has turned into and relaxation is the key!

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Price per night from

$1,031

❤️ Super Cozy Home Minutes to Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Birthday Trip!” I do believe this might have been the funnest trip I've ever taken in my life. Having every single thing just minutes away from you was such a delight and such a pleasure to not have to drive around constantly in the car. This community is gated and seems like a really fun place to actually buy a vacation home. Actually, while we were there we looked into it and might be doing the same thing that this particular person is offering on TripAdvisor as well! First of all, the house was just absolutely amazing... Bigger than my own home even. It was just me, my son and my husband and our house was absolutely humongous. We actually had thought we would have another family with us but it fell through. Everything was clean and perfect. There were many things like dishwasher, laptop, printer, hair dryer, straightener, toiletries, food! When we arrived, we already had some basic needs that were furnished To Us by the owners. It was such a treat to see that they really cared about us to furnish those things! There was a perfect screened in porch out the back over looking a little bit of a water marsh where we got to watch the birds everyday. The wildlife in our particular yard was extremely delightful. From frogs to lizards two birds two cranes we had an amazing time when we were relaxing at home. To my delight, there were also three swimming pools in the complex. One of the pools were in the middle of the community which was right down the street from our home, then there were two others inside the clubhouse which were also fantastic. We really enjoyed the hot tub and sitting underneath the shelter when it started to rain. Since I knew it would be very hot and we would be extremely exhausted, I asked for a maid service halfway through our vacation and I'm so happy I did. It was nice to come home after dinner to a 100% clean house with clean towels and everything perfect. I recommend that you get the service as the cleaning lady does an excellent job! The next time we booked our Walt Disney World vacation I will be using this home again without a doubt. Even though we stayed 7 days, we still did not get to see everything that we wanted to. Next time we come down we are doing 10 to 12 days for sure and cannot wait to come back to Vista Del Lago. I was really surprised on how many friends we made while we were there!! If you are looking for a family home that could easily sleep 7 people, please do yourself a favor and book this, you will be so glad that you did!!

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Price per night from

$252

***HUGE SALE $109N! Great Ocean View! Beach 5 Min Walk GYM/Sauna/GRILL

Miramar Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

“Great location, beautiful views, and nice accomodations” We had a nice stay here at the Ariel Dunes II. The location is great! It is convenient to the beach (a short, but nice walk), and there are also a couple of good beach-side restaurants nearby. There's also a good grocery store nearby within a very short drive, as well as many other shopping possibilities a traveler might need. The unit was nicely furnished and decorated with contemporary furnishings and was quite comfortable. I, for one, appreciate places near the beach that are not decked out with peach and teal walls or seashell sculptures from the eighties. :) The view was also quite nice from the balcony and I spent some nice mornings out there having breakfast while soaking in the sights and sounds of summer.

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$164

Luxurious 3 Bdrm Condo at Reserva Conchal located on the same property as Westin

Playa Conchal apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Morales Family” Our stay at Daphne's condo was comfortable, pleasant, and memorable! The condo is nicely furnished, spacious and clean. The location offers quick access to pool area and beautiful scenic view from balcony. The Conchal Resort offers excellent shuttle service to all areas within resort property and staff is very friendly. Daphne was very helpful in providing information and travel tips. We enjoyed our stay and plan on returning next year. Thank you Daphne!

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Price per night from

$687

3 Bedrooms Irvine Family Friendly Vacation Villa

Irvine townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$229

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