Westchester County Rentals

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10,034 Houses

“Great Family Memories” We give this home an A+!! Everything about it from the appearance, to the owner (Liz), to the location, and the management company combine to give you unprecedented good customer service that insures a great experience. Everything is geared towards you! The house is actually even nicer than the pictures depict!! We had 5 adults and one child stay and there was plenty of room for everyone. We loved the layout. Our granddaughter squealed with delight when she saw the Mickey Mouse room. She even asked to go to bed several nights!! We enjoyed going to nearby outlet malls, Disney, Disney Springs, restaurants close by, and even grilling out on the patio while family members swam in the pool. The game tables in the garage provided some lively competition. The greatest compliment you can give a place is to say you would return again. When we come back to this area again, Pilgrim's Paradise will be at the top of our list to stay at again! Liz made everything run smooth and was a delight to work with!! Thanks for sharing your beautiful villa with our family!!

Responds fast! avg. 1 hour 56 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$189

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,139

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$474

9Br/6Ba luxurious Pool House from $300/nt, Close To Disney

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 27 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$400

Grand Pacific Palisades - Two bedroom - Ocean View

Carlsbad condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$408

Beachside LUAU Sandestin 6th floor 1 bedroom TRAM/beach gear

Sandestin condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 1 hour 1 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$99

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.

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$399

♥EEV♥ South-facing Pool & Spa - Gated Resort - Games Room

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$113

Wheelchair Accessible, Roll In Shower, Pool Hoist, Luxury Disney Vacation Home

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$284

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$113

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 10 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$103

Private heated pool, single floor house. Golf community.

Chandler house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$251

8br/6ba pool villa from $280/nt , Close to Disney

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 27 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$343

♥EEV♥ South Facing Pool & Spa - Games Room - Gated Resort with Amenities

Davenport villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$113

Scottsdale, AZ - MULTI-MILLION DOLLAR - 5 Star Dream Vacation Private Resort!

Paradise Valley villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$3,422

Cork Way Villa

Davenport villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 37 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$165

Orlando, Villa With south facing Private Pool, Close To Disney

Davenport villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$137

Large Villa / private game room/yard

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Family vacation” My family was very impressed with the villa. Property manager, George, was very helpful. I would recommend this villa to others. My family will definitely stay at this villa again

Responds fast! avg. 3 hours 15 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$189

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$159

Embark Dream Vacation Home 40 People at Solterra Resort

Davenport house

  • 14 bedrooms
  • 6 bathrooms
  • sleeps 40

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,181

Remodeled, Modern Decor, Oceanview, Nice Balcony!

Arcadian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$457

Solara Resort 7BR 14 Guest Pool, Span, BBQ, Games NO Rear Neighbors

Four Corners house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$268

Newly Remodeled,Ocean View,Private Maisons Sur Mer

Arcadian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$78

DISNEY house! FREE heated pool, spa, game room, themed bedrooms, BBQ, Lazy river

Four Corners house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$319

New, High Floor, Private, Maisons Sur Mer, Direct!

Arcadian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$58

Right Next Door to Disney Windsor at Westside!

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$291

New, Oceanview Remodeled, Private Maisons Sur Mer!

Arcadian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$61

⚜Experience an Enchanting Dream Vacation 14BED Bowling/Games Room/Pool/Spa⚜

Davenport house

  • 14 bedrooms
  • 11 bathrooms
  • sleeps 28

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,044

Newly Added,Ocean Views - Private Maisons Sur Mer!

Arcadian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$58

Updated Oceanview Modern Decor, Private Balcony!

North Myrtle Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$35

New, Oceanview Remodeled, Private Maisons Sur Mer!

Arcadian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$115

Newly Renovated, Modern, Ocean-View, Great Balcony

Arcadian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 43 minutes

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$35

Pamper Yourself /14 BED/Bar/Lazy River in Solterra Resort

Davenport house

  • 14 bedrooms
  • 5 bathrooms
  • sleeps 36

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,118

⚜Indulge in Sunshine Bliss! Luxurious 7-BD Pool Home Awaits Your Escape!⚜

ChampionsGate house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Balcony or terrace Children's pool Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$383

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Windsor Palms Resort/southwestPool/GamesRoom/Gated

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Cozy and great location” Stayed for wife's birthday and it was great. Cozy home with all the extras. Big screen TV to watch the games, gameroom to keep the kids entertained, pool was nice size.10 to 15 mins away from the mouse named Mickey. I Will come again. Recommend 100%. Owner communication is superb...

3 of 4 match: Balcony or terrace, Golf course on site or within 15 min walk, Children's pool, Private outdoor pool (heated)

3 of 4 filters match

Price per night from

$400

House of Views-3 Bedroom 3 bath nestled on a beautiful golf course

Mesa house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Children's pool, Golf course on site or within 15 min walk, Balcony or terrace, Private outdoor pool (heated)

3 of 4 filters match

Price per night from

$599

Responds fast! avg. 1 hour 55 minutes

3 of 4 match: Children's pool, Golf course on site or within 15 min walk, Balcony or terrace, Private outdoor pool (heated)

3 of 4 filters match

Price per night from

$265

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

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Balcony or terrace, Children's pool

3 of 4 filters match

Price per night from

$205

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