Vacation Rentals & Condos in Madeira Beach

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Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$206

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$212

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

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$336

The Peninsula Clermont, Orlando

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent Vacation! Can't wait to go back” We absolutely loved your villa and the resort it was situated in. From the moment we arrived we enjoyed every minute. The house was very quiet and spacious. It can easily fit in two families of 4. The house was clean inside out. The mattresses were plush and bedding soft. The Mickey/Minnie room was super cute and my kids' favorite! We all slept like babies every night. The furniture was solid wood and looked brand new. It was also nice to have a kitchen with anything and everything we needed. It's a paradise to have that much space for a vacation. All theme parks including the Lego land were easy to access. There were Publix, McDonald, Danny's close by with plenty of choices to eat out. We were not able to swim in the pool or check the clubhouse. Will try out next time. The view from the backyard was gorgeous! We would definitely be back again soon. I would be happy to refer any friends thinking of travelling to Orlando area.

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$131

Responds fast! avg. 3 hours 10 minutes

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$287

Luxury Vacation Home Near Disney

Davenport house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$343

8BR Charming Villa near Disney, Theater, Pool, Spa

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Responds fast! avg. 2 hours 36 minutes

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$287

beautiful condo with magnificent views of mandalay

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$153

HOME AND BARN HACKING DISTANCE TO WEF

Wellington farmhouse

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$974

Golf - Florida 3 Bed Villa on 99 Hole Golf Estate

Rotonda West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great Location to Beaches- Quiet Getaway” My husband and I have previously lived in Southwest Florida and have been trying to get back for a vacation for a few years now. This house was perfect for our needs. The house was well stocked and comfortable. Our kids ages 12, 10, and 5 had a great time! Our only minor complaint was with the pool. It was pretty chilly since it is solar heated. My kids still got in, but it was too cold for my husband and I. The management team made everything very easy for us. We would like to visit again!

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$189

Disney, Universal, Beaches, Golf, New Rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$218

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$336

⭐⭐⭐Disney Contemporary 3 ⭐⭐⭐

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

“Cheerleading Comp” We had a great time and the house was more then we could ask for. There was so much room the beds were all very comfortable . The house was clean it ready for our stay on time. The pool was clean large area to sit and relax. The rooms were large and had lots of room for your things. The area is very quiet and close to everything. I will for sure rent this home again in the future and would recommend to friends and family.

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$281

“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: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$189

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

“Decent place but lacking in some areas” For one week in July 2014, my family from Alabama to Alaska (with us from Canada) all stayed at 928 Solona Circle. Overall we were happy with the house rental but do not stay here if you need assistance with anything. It took my 4 phone calls over 3 days to just find out what the Wi-Fi password had been changed to (the one that we were emailed was incorrect). It may not be the safest neighbourhood as there were police men in the gated area twice during our stay. And the house was filled with broken outlet covers and had very dirty couches, which needed steam cleaning. It was a spacious home and we loved the walk-in closets as well as the ease in which to find it and the easy drive to Disneyworld. But if you want to stray there, you need to supply everything- even your own toilet paper and Kleenex. The jets ion eth hot tub did not work and the game room had a broken foosball table. Overall we were mainly happy with our stay but were disappointed with a few things.

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$189

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$331

Storytellers Villa

Four Corners villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Truly Amazing” Storytellers the most amazing place to stay. I will definitely return. The owner was always prompt on responding to emails and went above and beyond helping us with our stay. My family and I enjoyed the pool, the cinema, and spa during our stay. We had absolutely no problems with our stay at Storytellers. My 5 year old granddaughter loved the Frozen Room and didn't want to come home. The house is so inviting and beautiful. This house is a must if you are planning a trip to Kissimmee area.

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$395

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$338

Surprise Yourself With Unforgettable Deluxe Villa w/ Private Pool+Spa+Baby Gears

Four Corners villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$402

Serene & Attractive Pool Home Near Gulf Beaches

Estero house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 19 minutes

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$229

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$182

“Very welcoming and worth it !” Me and my family absolutely loved this vacation house everything was so welcoming and near perfect ! This house is definitely something we will never forget and hopefully when we come back we will be able to rent from kim molnar again ! Everything was to a T ! Thank you so much kim !

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$458

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: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$400

Highland View 6BR Villa Private Pool/SPA Near Disney

Four Corners villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

Responds fast! avg. 2 hours 36 minutes

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$248

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$402

Venice Immaculate RemodeledHome-2 Bdr/2 Bath-Pool-WIFl&CABLE-2 Miles to Beach

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$172

Treat Yourself and Family to a Deluxe Villa w/ Superb Rooms+Private Hot Tub

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“A good choice for our family” This place was as expected, except that the floors needed mopping. This home is advertised as children friendly, but bare feet and small children soon became dirty by crawling on these floors! We began our stay by double mopping both ground and upper floors, as well as the stairs. Other than that, we were happy with our stay, and would choose this place again!

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$137

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$402

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$177

Solterra | 5 Star Resort | Disney Area 4654

ChampionsGate villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 1

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$121

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: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$103

⭐Deluxe Villa+Private Pool+Hot Tub+Theatre Room+Pool with Waterslides⭐

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$401

Spacious modern pool home, Family & Golf trips - 4727

Hernando house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$315

The Gables of Vero Beach

Vero Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$401

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

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$182

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$490

Responds fast! avg. 2 hours 20 minutes

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$217

Amazing Villa with south facing pool and conservation view

Orlando villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Golf course on site or within 15 min walk

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Price per night from

$228

Viewing 38 of 3,653
rentals in Madeira Beach

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