Chestnut Hill Rentals

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12,768 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: Heated pool Games room

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Price per night from

$149

The Charming Mickey's Tree House,

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Mickey Mouse Hut” Wonderful home. Everything you need for a home away from home. Pool was awesome. More than enough pool towels to use. Home was very spacious. Only complaint I had was it was not enough cookware to use to cook meals enough for a large group. Other than that small gesture, I give it 5 stars. Thanks for letting us share another vacation in Florida in your home.

Responds fast! avg. 2 hours 46 minutes

Match: Heated pool Games room

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Price per night from

$123

20 mins to Disney, Immaculate 6 Bed, Private Pool

Clermont villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$218

Gorgeous apartment just minutes to Disney parks, Orlando Florida.

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful Place to stay” I stayed at the Island Club for a period of 3 months and was very happy with my stay. It was quiet, and comfortable. I liked the layout of my condo which was on one floor. My family of 5 had plenty of room to enjoy. I also liked how there was a patio in back. It made it feel more like a home. We stayed on the top floor where there was vaulted ceilings and lots of windows in the front room. This made it feel more spacious and rich. The amenities were additionally nice as well. There were 2 different pools and jacuzzis, tennis court, clubhouse and work out room to enjoy. I also liked how you could park right up against your condo building. The location was very convieinent as well. It is close to all major attractions. 15 minutes from Disney - 25 from Universal and close to shopping, and restaurants. I would stay here again in a heart beat!

Match: Heated pool Games room

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Price per night from

$125

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great Stay” The house was a better option than hotel rooms. The house was very clean and they had everything necessary for a pleasant stay. They also provided pool towels for the pool or jacuzzi. The jacuzzi was nice and hot and a good option in the evening. Each bedroom had a TV and they had a pool table in the garage. It's a quiet neighborhood. It's not far from Disney or Walmart for groceries.

Responds fast! avg. 2 hours 44 minutes

Match: Heated pool Games room

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Price per night from

$121

Caledonia Lodge - fabulous 5 bed villa nr Reunion

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Love it” me and my family loved this place,kids love the pool me and my wife loved the game room,for peace and quiteand my dauthers love all the space they had.

Responds fast! avg. 1 hour 17 minutes

Match: Heated pool Games room

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Price per night from

$161

Close to Disney,Seaworld,Convention Center,4br Townhome with Hot Tub

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great Family Friendly Home” We had a blast. It felt safe and secure. It was clean and spacious. I have a large family of 9 and everyone had plenty of space. Quiet but friendly neighbors. Amenities were awesome. Hot tub was so relaxing. We had a great time.

Responds fast! avg. 1 hour 27 minutes

Match: Heated pool Games room

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Price per night from

$132

“A great and fun place to stay” The house is spectacular. Very very well stocked and the manager Al made sure we had everything we needed and even came out a couple of times to quickly address any concerns we had. Very very close access to the beach and dock. Garage well stocked with water toys, chairs, fishing rods, etc. Everything you need. Abundant toiletries, towels, games and entertainment made for a very comfortable stay. Gift basket was a nice touch. Super easy checkout! We will definitely look to rent from again if we ever come back to the area, which we hope to do someday. Thanks!

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Price per night from

$228

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Price per night from

$287

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

Match: Heated pool Games room

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Price per night from

$138

3 bedroom home private pool near Disney I4 & shops

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Supervisor” It was really nice. We stayed for three nights and we enjoyed it. It was close to the parks, to publix, restaurants, and gas stations. Only one negative was that there were no phone signal.

Responds fast! avg. 44 minutes

Match: Heated pool Games room

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Price per night from

$121

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

Match: Heated pool Games room

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Price per night from

$132

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Heated pool Games room

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Price per night from

$1,118

PRIVATE BEACH OPEN** Beachfront bungalow 4BR *Htd POOL*Pet

Indian Shores house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“A wonderful place to be!” Our rental was right on the pool/beach. It was perfect! Gorgeous pool and the beach - beautiful, private - everything you could want. The cottages were spacious, clean and kitschy. They had everything you needed. You could tell good people stayed there as everything was well kept and stocked. The owner, Liz, was lovely and even though we had no pets, every pup there was well behaved and everyone was respectful of the rules. The people staying at the other cottages were wonderful and had stayed there before. Obviously Liz knows what she’s doing . My parents also stayed with us and both of them loved the place. The beds were very comfortable which doesn’t always happen in rentals. Hoping to see you next year! Cheers!

Match: Heated pool Games room

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Price per night from

$487

Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

Match: Heated pool Games room

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Price per night from

$207

Life is better on the beach! Renovated - Beach Chairs Included !

Panama City Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Match: Heated pool Games room

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Price per night from

$190

NICE BEACH CONDO DIAMANTE AREA

Acapulco apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool Games room

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Price per night from

$160

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Heated pool Games room

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Price per night from

$212

Marriott's Royal Palms Resort Orlando Near Disney

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool Games room

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Price per night from

$171

Sweetbay Villa

Clermont house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great home.” Everything was as pictured. Clean and quiet area close to many restaurants and shopping. Owner was easy to work with and responsive.

Match: Heated pool Games room

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Price per night from

$207

“Great House!” The owner was very attentive and accommodating. We didn't have wifi the entire time we were there. The placement didn't allow for anyone to use it in the house. I would suggest moving the cable router to the main tv room. Use a splitter and you're in business. Otherwise it was a great house for the price!!

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Price per night from

$167

2 bdrm 2 ba condo across from White Sands Beach

Kailua-Kona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful Paradise” This immaculate well maintained condo came equipped with everything needed to snorkel, body board, picnic or just rest by the ocean. The view from the balcony was breathtaking. The condo grounds, pool area, hot tub and barbecue were very well maintained. The office staff, Kitty , welcomed us when we checked in and represented the condo owners with courtesy and kindness. The owners provided us with locations of stores to purchase groceries or whatever needed. Their personal touches on their condo made us feel like we were at home.

Responds fast! avg. 1 hour 25 minutes

Match: Heated pool Games room

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Price per night from

$176

Disney Pool Home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Heated pool Games room

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Price per night from

$218

Caribe Cove Resort - 2 BR * Unit Top floor * New Mattress - WiFi/Parking free

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool Games room

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Price per night from

$253

Watersong Resort | Pool & Spa | Games Room 338

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Heated pool Games room

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Price per night from

$120

IRRESISTIBLE! 5* 3rd FL GULF FRT! 2BR 2B, *Free Bch Setup Mar-Oct *1:30cst ck-in

Panama City Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool Games room

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Price per night from

$400

9 Br/6 Ba luxurious Pool House from $380/nt, Close To Disney

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Great time!” House was a perfect fit for my family. We had a great time and plan on making this a yearly trip. Central to everything, but far enough away you didn’t feel trapped. Would highly recommend it!

Responds fast! avg. 1 hour 27 minutes

Match: Heated pool Games room

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Price per night from

$344

HOME ON the NIAGARA RIVER - 4 BR POOL - HOT TUB NEAR NIAGARA FALLS RIVERFRONT

Niagara Falls house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Cozy house on the Niagara River” This house was fabulous for our weeklong stay. One of the most important things for me was that I was able to do my work. The internet connection was fast and reliable. The house was very comfortable and clean. The house is directly on the Niagara River in a quiet neighborhood and just across the street from The Riverstone Grill restaurant. We enjoyed eating at The Riverstone Grill twice during our stay. As long as I'm mentioning restaurants, we also ate at Dick and Jenny's on Grand Island and that was an excellent meal as well. The house has everything you need for your stay. Linens, extra blankets, towels, dishes, snacks, full kitchen, clothes washer and dryer, toiletries, games, videos, and even a high chair. Glenn was always just a phone call away and was wonderful about helping us whenever we had questions.

Match: Heated pool Games room

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Price per night from

$310

Boho Chic Music Promoter Guest House w/ Pool The Malibu Retreat

Malibu guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 9

Responds fast! avg. 3 hours 53 minutes

Match: Heated pool Games room

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Price per night from

$438

The Ultimate Florida Vacation

Poinciana villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” Very cozy, out in suburbs. Neighborhood clean and friendly. Pools and outdoor basketball courts and activities for the kids.

Match: Heated pool Games room

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Price per night from

$110

Best View of North Beach to Aventura! Stunning Sunrises!

North Bay Village apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Heated pool Games room

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Price per night from

$86

Our GULF FRONT CONDO2 at Pelican Walk

Panama City Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“:)” It was wonderful we enjoyed every second recommended for a friend I will stay there next time thank you thank you thank you

Match: Heated pool Games room

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Price per night from

$258

Match: Heated pool Games room

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Price per night from

$228

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

Match: Heated pool Games room

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Price per night from

$206

OCEAN VIEW STUDIO AT BEACH FRONT RESORT

Ka'anapali hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Heated pool Games room

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Price per night from

$1,031

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

Match: Heated pool Games room

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Price per night from

$344

DISNEY area Vacation Home at Regal Palms sleeps 9 w/Free WIFI

Davenport townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

“Great place!” Loved the area, away from the traffic, very pleasant. Will stay again. Family enjoyed it. Great way to separate older kids.

Match: Heated pool Games room

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Price per night from

$217

Spacious Disney pool home w/ Spa, near golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“PERFECT FAMILY VILLA!” This villa is HUGE and gorgeous! We were traveling with a large family and with 7 bedrooms and 9 beds plus a crib in the master there is more than enough room for your whole family to enjoy a get away! There are 2 rooms located down stairs so if anyone is disabled they can use these rooms. This home is beautifully decorated and so comfortable for us. We thoroughly enjoyed the screened in private pool -with a bathroom entrance right off the pool area! We felt very safe in the community this villa is in and the area surrounding it. Champions Gate is a gorgeous little community with everything you need within 10 minutes. We were visiting Disney and found this villa a wonderful option to staying in the parks. It took us 15 minutes to get to any park and we always parked and loaded a tram quickly and went right to the door. I don't know why people have always convinced me staying of property would be such a hassle..it was no hassle at all! A lovely bonus to this villa was an ice cream truck driver lives right down the street and hits the neighborhood 2 times a day. The kids LOVED that! The home came with all the comforts needed to make us feel at home. Including pool toys, 2 high chairs, iron/ironing board, hair dryers, big beach towels, bath towels and rags, kitchen towels and all the cooking utensils and appliances needed for cooking meals. We did have a dilemma with an odd shape staircase that our child gate would not fit and a toddler but we just moved a couch to block the entry from the livingroom to the front area and that worked well. The home is tiled so it was easy to keep the floors clean. The beds were comfortable and the pillows were mixtures of full and flat to suit all preferences. The home smelled nice and did not have the mild moldy smell many FL homes can have from the high humidity in the area. The owners were a pleasure to work with, very accommodating, helpful and prompt to answer my silly questions about where items in the house were and how to work locks etc We will for sure stay here the next time we visit orlando area. This villa felt like home and was hard to leave. It truly is so comfortable and I am a hard one to please! If you are reading this and considering this home...seriously do not continue your search. There is so much that can go wrong when renting homes on vacations. But this one does everything right!

Match: Heated pool Games room

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Price per night from

$212

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