Westchester County Rentals

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10,038 Houses

“Disney vacation” Beautiful vacation home! We loved the spacious living arrangement and proximity to a shopping center. Only about 15-20 minutes to Disney parks. Would certainly recommend this house and stay again!

Responds fast! avg. 30 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$170

5-star LUXURY RESORT:Tennis, Pool, Spa, 3 acre Estate near Beach, Golf, Races

Rancho Santa Fe house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,088

The Ever After Estate - 13BR Sleeps 45 People & Has 62 Private Acres

Clermont house

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 43

“Everything you could ever imagine !!!” My new Wife and I just got back from our stay. We held our Wedding there. We had both our immediate families stay with us during 3 days of our 4 day stay. Plenty of room for all, we had 15 adults and 8 kids total. This place is just so amazing. My wife and I toured it prior to our stay and missed so many things because there is so much detail. Our favorite place was the pool area. The day after our wedding some of us hung out at the pool for a couple of hours. The kids all had a blast between the pool slide, video games, ball pit, mini golf, and movie room. This made it easy for us to focus on set up and tear down for the wedding. We had 220 guest during our day and everyone loved the place. Biggest question was how did you find this place. Great photos from our day hit facebook immediately with babies on the Carousels,kids playing mini golf, and people around the tropical pool setting. Andrew, Felicia, and his staff were very helpful. Andrew answered all our questions with fast response times through out the planning. Felicia was there when we checked in and ensured we were settled and answered any last minute questions. The detail andrew put into his Estate is amazing. Every thing out there takes you away from your everyday. We are so lucky that such an awesome place was shared with our family and friends to enjoy. It was the perfect place to hold our special day. The last day I spent an hour taking photos of the Estate in which I noticed the incredible landscape,a touch that just simply takes your breath away on the beauty of life. Andrew thought of it all. The only down fall, which was our fault, is that we did not have enough time to enjoy everything. This was due to a short stay, wedding set up and tear down. Our next stay will be longer. My older Sister from Philly was talking about a family meet up next year. Boy I Hope so. All our Wedding dreams came true. Thank you Ever after Estate and Thank you andrew.

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,985

“Harbor View Grande Suite # 707 Excellent 5 Star *****” A Big Thank you to the owners and Staff of 707. The accommodations where beyond our expectations. The décor was professionally done and the Suite was spotless upon arrival. The champagne was a special treat and all the beach chairs, umbrellas, coolers for our use was that extra touch. Harborview is centrally located to all shops and restaurants. The balcony views from sunrise to sunset was truly magnificent. Highly recommend to all friends and relatives. Will definitely return. Thanks again. Anthony David

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$269

THE SANIBEL SUN CASTLE Luxury home, heated pool, great location, bike to beach

Sanibel Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$573

“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: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$189

The Harmoni in Serenity - Orlando

Clermont house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$126

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,143

Beachway Per Ankh - **Private Heated Pool Minutes From The Beach**

Pompano Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$373

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$292

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: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$476

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: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$400

North Myrtle Beach • Oceanfront • Booking for 2024!

Myrtle Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$252

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$321

⭐ Sensational Large 7 Bedroom Home with Pool,Hot Tub,Games Rm, 5 Min Disney ⭐

Four Corners house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$401

Responds fast! avg. 1 hour 31 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$968

20% OFF Sale Prime Location. Heated Pool, Game Room, Grill, near Disney World

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$182

Responds fast! avg. 2 hours 20 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$217

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$363

Villa by Disney

Davenport villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“idilic location/ perfect for visiting theme parks” Service from owners fist class. House was exactly as described. Ideal location for theme parks and shopping and eating. Could not get grandkids out the pool they absolutely loved it. 2nd time we have stayed there and will have no hesitation booking again should we go back to Florida.

Responds fast! avg. 1 hour 18 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$144

Highlands Reserve villa :South facing private Pool

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$208

Windsor Hills Retreat Villa

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$458

A little piece of paradise: Villa Santorini on the Lake

Rotonda West villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$195

229 -TROPICAL RESORT LIKE HOME. CLOSE TO BEACH. PRIVATE HEATED SALT POOL/HOT-TUB

Deerfield Beach villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 51 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$395

Tides-N-Tunes

Cape San Blas house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 21 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,214

Be Beautiful

Cape San Blas house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 21 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$890

Windsor Hills Disney Townhouse, Newly Redecorated

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$160

Remodeled, Modern Decor, Oceanview, Nice Balcony!

Arcadian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 41 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$457

Watersong

Cape San Blas house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 21 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$895

Florida Golf Vacation Villa

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$338

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

Four Corners house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$320

Calabay Palms Villa - Luxury 5 Bed - Sleeps 10/2 - South Facing Pool - Hot Tub

Four Corners house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$244

Lovely 5 Bedroom Home Close To Disney

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$259

Off the Hook

Cape San Blas house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 20

Responds fast! avg. 3 hours 21 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$1,286

Sandy Bottom

Cape San Blas house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 21 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$563

Sea View Place

Cape San Blas house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 21 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$470

Responds fast! avg. 11 minutes

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$630

Match: Cot available Balcony or terrace Private outdoor pool (heated) Golf course on site or within 15 min walk

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Price per night from

$802

Viewing 38 of 10,038
rentals in Westchester County

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