Emerald Isle Kissimmee Rentals

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166 Houses

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$401

Match: Cycling trips

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Price per night from

$401

Great rentals within 20 miles that match your search

Luxury Condo, Steps to Disney, ESPN, Free Wi-Fi, parking, Unbeatable location

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$91

Swiss 45 - Swiss Waterski Villa

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$401

Match: Cycling trips

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Price per night from

$287

Family Golf Resort 'Villa Bonita' Southern Dunes

Haines City villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“nice house” everything was updated and nice ,except for the mattress they are very old every time we when to sleep and got up we had back paint everybody, and everyroom they need to updated...other then that it was very nice

Responds fast! avg. 1 hour 17 minutes

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$121

Spacious 4-bed lakeside pool villa near Disney

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great Location” We stayed from Saturday to Saturday. Overall the house was good. Pros: Clean, spacious, close to Disney Parks, close to stores, very quite place, easy access, comfortable furnitures, Cons: master bedroom was hot, internet service went down mostly at night time like it has a timer at night, and odd times during day time only for few minutes, the pool only the first day when we arrived pool was with cloudy water and water very hot all the time, we think the heater was on. Cable TV, we had two afternoons that we had no signal. The house has two blenders both not working. No raw meat knife, we had to buy our own for cooking. We wanted to use the garage to place our car, it has many objects we could not use it.

Responds fast! avg. 1 hour 57 minutes

Match: Cycling trips

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Price per night from

$162

❤️ 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!!

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Price per night from

$252

Spacious condo | extra amenities | epic lake-view

Orlando apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Everything we could have wished for and more!!” Just back from a two week stay here. Condo looks exactly as it does in the photos, stunning! We have been to Orlando many times, however this is by far the best condo we have ever stayed in. Everything went really smoothly, from booking, paying and getting all the necessary information required. The location is excellent, close to parks and the pool was great also. We had decided to take it "easy" this time round in Orlando and having such a beautiful place to stay in was wonderful. Great to sit outside on the porch in the evening watching various fireworks and enjoying the evening sun. The condo was also well equipped and felt really at home here. Would recommend and hopefully will return soon.

Match: Cycling trips

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$196

❤️ 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: Cycling trips

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Price per night from

$401

From $110/nt,Near Disney,Seaworld,Convention Center,4br/3ba townhome with hottub

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

Match: Cycling trips

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Price per night from

$132

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Price per night from

$171

Charming 3-Bedroom Home w/ Sun-Kissed Private Pool

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$158

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!

Match: Cycling trips

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Price per night from

$227

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: Cycling trips

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$132

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$121

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: Cycling trips

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$149

“Good price for family of 10” With 5 bedrooms, fits 10 comfortably. Owner is very helpful and location is 20mins from the parks. Walmart and restaurants are very close.

Responds fast! avg. 1 hour 27 minutes

Match: Cycling trips

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Price per night from

$149

5* Windsor Palms, Conservation View, South Facing!

Orlando house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$212

Unique 5 Star Home - Private Pool, Free SOLAR Pool heat, WIFI, BBQ, Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Violet lane” Home was clean and charming.We enjoyed the pool and privacy greatly. Owner thought of most anything we may need, except one; toilet paper. This was our first time staying in a private home rather than a hotel so perhaps it isn’t a given but if we had known, it would have saved us an immediate trip to store. I cannot speak for other guests but felt that not starting laundry, despite stating was not mandatory, not doing so may affect my deposit. A few other minor issues: missing ping pong table, “key?” to working slot machines, how, or if, the ice maker worked and where the garage door opener was located(we did find on the furnace in the garage the day before we left), and whether the swinging chair was safe to use, despite the crack, may have been problems easily remedied with a phone call but ultimately not important enough to bother owner and take time away from us. Not meant to be a negative review, it is not. Overall, we had a lovely time and would stay again. However, it seemed important to be honest in regard to our experience.

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Price per night from

$149

YOLO HOUSE, WINDSOR WHERE LUXURY MEETS ADVENTURE : POOL / SPA INCLUDED

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

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$575

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Price per night from

$218

4bdrm Family Villa, Home away from Home!

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$178

Luxury Resort Villa- 3 miles to Disney- Free Wifi

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$109

Victorias Villa Upgraded 4 Bed 3 Bath Solar Heated Pool/Spa

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Cycling trips

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Price per night from

$172

Large 7 Bedroom House on Emerald Island Resort

Four Corners villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$184

Awesome House on an Awesome Resort....Orlando area

Haines City house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$126

Disney Vacation Condo - stay 6 days get 7th FREE

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Owner is awesome. Goes beyond to satisfy guest” This is a 3 bedroom 2 bath unit. Unit has everything you need. It was clean except for the carpets. I called the owner and she asked what did she need to do to make this better. I said clean carpets. She sent Stanley Steamer out to clean them! That was awesome! Loved that we had washer and dryer in the unit. The unit does need some TLC. Deck attached to the master is in need of repair and the bathroom could use and update for sure. We enjoyed our stay and it was very comfortable! Owner is fabulous to work with...best ever!

Match: Cycling trips

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Price per night from

$100

Sunny Pool Home, Gated Resort near Disney

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 48 minutes

Match: Cycling trips

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Price per night from

$184

Disney Pool Home in Gated Resort near Golf

Orlando villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 48 minutes

Match: Cycling trips

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Price per night from

$132

Debbie's Florida Retreat a Luxury Vacation Home

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Fabulous Stay in Kissimmee” We loved staying at this home. It was so fun for the kids to have a private pool and so convenient for us as parents. The house has everything you need to make the stay easier...including a crockpot and belgian waffle maker. It was a nice distance from DisneyWorld. The only negative was the distance to Universal Studios. We would totally stay at this home again! We loved it! Also, Chad and Debbie are easy to work with and quick to respond and help your stay work well. We had initially booked to come in March 2020 and had to push it back a year due to covid-19. They could not have made the process easier.

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$217

Disney Vacation Villa 5 br/3 ba (pool, game room)

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$184

Scotty's Luxury Orlando Villa - Snowbirds welcome

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$172

Beautiful 7 bedrooms, South Facing Pool Spa, 3 miles to Disney, Key Less Entry

ChampionsGate villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 14 minutes

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$344

Spacious and Clean, Pool and Spa, Wifi, Keyless Entry,Close to Disney, 4 masters

Four Corners villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 14 minutes

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Price per night from

$344

Disney 5 Star Vacations / The Osprey Villa

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Great House!” Great house, lots of room for 8 adults down for a golf trip. Close to all of the courses we played. Celebration, Mystic Dunes, Falcons Fire, Orange Lake. The longest drive we had was 15 minutes! House was very clean with plenty of utensils, plates, glasses, and towels.

Responds fast! avg. 30 minutes

Match: Cycling trips

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Price per night from

$172

Villa Mirasol - one of the best houses at Reunion

Reunion villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$374

“Great stay” Pro- This home is huge! Plenty of living space for a big family. Hot tub and pool were heated. Beautiful decor!! Really comfortable beds. We were so close to Disney very convenient to jump right on highway. Championsgate was very nice. Owners were so responsive whenever I had a question. Cons- The hot tub takes awhile to heat up to max heat. The t.v were a little complicated to work. We were so tired after a day at the parks it wasn’t a big deal for us. Some little things should be updated but nothing major (like missing pieces to games, remotes, and the cover to hot tub) We really enjoyed this house and would stay again! Thank you!!!

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Price per night from

$400

Viewing 38 of 166
rentals in Emerald Isle Kissimmee

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