Vacation Rentals & Condos in Madeira Beach

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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: Cot available Golf course on site or within 15 min walk

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$217

“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

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Price per night from

$170

“Excellent and perfect House for vacation.” this was my first experience and was the best, perfect area, all was close in case we need to buy something. The house was full equipped for everything you need and very clean. The state park pass was excellent, with access to a perfect beach. we had a very great and fun time with the family.

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$264

Luxury 6bed 5.5bath Extended Pool Villa Nr Disney. Guard Gated 5*Resort

Davenport villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 13

“BEAUTIFUL!!” Everything was even better than we expected. The villa was exactly as pictured in the online photos. Very spacious, clean and quite serene. SIMPLY BEAUTIFUL!

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$195

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 Golf course on site or within 15 min walk

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Price per night from

$1,985

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

Sanibel Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$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

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Price per night from

$189

The Harmoni in Serenity - Orlando

Clermont house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$126

Upgraded 5-star Penthouse, Bahama Bay near Disney

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Very comfortable stay - enjoyed every moment of it!” Very spacious accommodations. We stayed 2 families with little girls who were very anxious to see Disney World parks. The condo was perfect for our stay, we were just about 20 minutes from Magic Kingdom so we were there in a snap. The resort is beautiful and we can't wait to come back again. There are multiple swimming pools, one close to condo's building, another one - bigger and open until 10 pm - near the club house / reception. Another similar size pool at the restaurant area with little white sand beach, volleyball net and table tennis. Also we enjoyed playing tennis on the real hard court surface near reception, very good quality and with lighting. When you need a day off from visiting parks and all these crowds staying on the resort is the great option. Shopping is very close to the resort - 7 minutes drive to Walmart, so you could get anything you need, open 24 hours. We also recommend buying tickets to all attractions at the Walmart since there is a small discount vs buying at the gates. Overall - great experience, highly recommend to anyone. Will definitely come back again!

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Price per night from

$227

❤️ 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!!

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$252

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Price per night from

$292

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...

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$401

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 Golf course on site or within 15 min walk

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Price per night from

$476

Responds fast! avg. 33 minutes

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Price per night from

$213

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 Golf course on site or within 15 min walk

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Price per night from

$400

ADVENTURE ISLAND & Busch Gardens Home

Tampa house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

“Home away from home” The home was magnificent, very spacious, very clean, the decor was awesome!!!location is great we all loved it Mr Sidney was very nice the rental process was very easy. Thank you we will rent from you again.

Responds fast! avg. 2 hours 59 minutes

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$190

♥ Orlando Disney ChampionsGate Golf 8BR/5BA Vacation Home (9093)

ChampionsGate house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

“GREAAAAAT” This house was awesome...very clean had everything For You To Use. I Will Highly recommend this house For Everyone!!! Thank You so Much For an awesome Experience..we Loved It...We Will See You Next Year!!!!

Responds fast! avg. 1 hour 40 minutes

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$373

UNIQUE LUXURY POOL VILLA - Private Pool/Golf View/Fully Refurbished Aug 2017

Haines City villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 20 minutes

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Price per night from

$217

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Price per night from

$321

❤️ Super Cozy Family Friendly Home, Private Pool, Hot Tub, Minutes to Disney

Four Corners house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

“Perfection In Every Way - An Unequalled Family Stay” Not only did the kids totally adore their themed rooms, the adults couldn't have been more delighted with our Serendipity rental. We were 3 families: 6 adults, 1 child and 2 infants. We celebrated Grandpa Norm's 70th birthday at Serendipity and at Walt Disney World. When we found Serendipity on Tripadvisor Flipkey, we immediately knew this was the perfect place to base our family for our Florida celebration and once we were in touch with the owners, Ken and Sarah, we were confident we had made the right choice. Every detail of our planning was enhanced by prompt replies from Sarah to our inquiries and every detail of the home in pictures and description on Flipkey were accurate to a "t." Each family could enjoy their privacy if they desired in their separate bedrooms with private baths but the living space made for a gathering of the entire family for companionship, conversation and dining effortless. And the outdoor space and pool area added to our family time together, especially after our long days at the Disney parks. We never felt crowded indoors or out. Every room and the outdoor area appeared to be professionally decorated. Sarah and Ken had supplies (cereal, milk, juice, coffee, bread, jam and much more) waiting for us so we didn't have to make a trip to the grocery store our first venture out. The house is located close to the parks, shopping, restaurants and grocery stores and Ken and Sarah's secret directions to the parks were flawless and fast. We had a couple of special requests re parking and items needed for the infants. The special requests were handled right away and the supplies for infants (see Flipkey description) was unbelievable - oh, and the gameroom! A man cave and kids cave dream come true and if anyone had wanted to golf - there were even golf clubs provided among numerous other resort quality extras. Well, I could go on and on but let me say: Don't hesitate to stay at Serendipity. Sarah and Ken will make sure you are comfortable in every way and that your every question about the house and planning your activities while visiting the area are covered. You will call them friends, as I do, even though we only corresponded by email. Again, I will say: Serendipity is perfection!

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$401

⭐ 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 Golf course on site or within 15 min walk

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Price per night from

$401

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Price per night from

$247

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

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$182

Disney Area Family Villa, Orlando - Golf Course Views (Sleeps 10)

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 30 minutes

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Price per night from

$201

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Price per night from

$490

Responds fast! avg. 2 hours 20 minutes

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Price per night from

$217

Luxury 4 bed villa, south facing pool, water view

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$178

Beautiful Disney Villa in Championsgate

ChampionsGate villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$360

Near Disney, 5 Star Princess Themed Home and Resort

Kissimmee house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$657

Lilo's Paradise in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$802

Responds fast! avg. 2 hours 20 minutes

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$217

Villa Bayside - Modern Coastal Designed Home

Cape Coral house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$344

“Another perfect stay!” It couldn't have been more perfect! Christmas and New Years in paradise. Of course, we are biased, we are the owners, but every time we get to come and enjoy our house we thank our lucky stars that we bought it. Its a great mix of comfort and luxury and we love our afternoon snacks and a drink while watching the sun go down. This year we had the family down again for Christmas (on the lanai!) So much fun to entertain at the big table and share a meal. Even though it was a bit chilly we turned on the pool heat and had a consistent 90 degrees...the moonlight swims were fabulous! Whats also great is that it is such a quick drive over to the beach, we can just hop in the car in within 15 min be down there for the sunset, New Year's fireworks or just a stroll. Looking forward to our next visit!! We hope you will enjoy the house as much was we do!

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$229

Hollywood Florida Vacation House Pool, free golf - Cribkeys

Hollywood house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$252

Jasmine Villa. Beautifully positioned overlooking lake and preserve

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$196

Disney Pool Home in Gated Resort near Golf

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 48 minutes

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Price per night from

$132

KYLEMORE

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$184

Emerald Island Villa,3 mi to Disney,Water View,4BedRm/3Bath,Gap Discount,Pool

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Cot available Golf course on site or within 15 min walk

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Price per night from

$171

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rentals in Madeira Beach

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