50 Best Vacation Rentals in Emerald Isle Kissimmee - Holiday Lettings - Cabins

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Emerald Isle Kissimmee

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50 Vacation rentals

(6) Very Good 

20

Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
A luxurious 4 bedroom, 3 bathroom vacation villa features a large private south facing pool and spa with conservation view plus fully air conditioned rooms and tv's and dvd's in living room and all bedrooms. The home is on the superb Emerald Island Resort and close to  …see more

from $95 / night

$662 - $838 / week

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from $95 / night

(9) Excellent 

48

Vacation villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa is situated in the beautiful Emerald Island Resort, regarded as one of the best resorts in the area. It is located south of Hwy 192 near Mile Marker 5 just minutes from I4. It is approximately 4 miles to the gates of Walt Disney World and within easy reach of  …see more

from $111 / night

$1101 - $1300 / week

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from $111 / night

(2) Excellent 

15

Kissimmee Vacation villa accommodation

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
Just as the name suggests, Emerald Island Resort is truly a tropical oasis. Nestled within a protected wetland, a unique vacation destination. Emerald Island is located minutes from Walt Disney World and the myriad other resorts and activities that bring millions to Or  …see more

from $185 / night

$1296 / week

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from $185 / night

(18) Very Good 

20

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Swimming pool
The home is a beautifully furnished and spacious property, well-maintained by our Management Company. It is situated off Highway 192 in the prestigious Emerald Island Resort, one of the premium vacation communities in the area, a tropical oasis nestled within prote  …see more

from $164 / night

$1103 - $1487 / week

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from $164 / night

(4) Excellent 

28

Vacation home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 50 mi
  • Swimming pool
This home has it all !! *Newly Installed Granite kitchen worktops* Our 3,400sqft beautifully decorated Villa is a Luxurious 5 star, 7 bedroom, 5 Bath home, a Private Screened-in South Facing Pool and Jacuzzi with a beautiful view over a lake and preserve, (no homes beh  …see more

from $200 / night

$1394 / week

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from $200 / night

(14) Very Good 

29

Vacation home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully furnished luxurious 6 bedroom, 5 bathroom pool home is ideal for the guests who are looking for that perfect Disney vacation. Luxuriously decorated and furnished throughout by an interior designer, our home will sleep 12 people in comfort and style and  …see more

from $162 / night

$1134 - $1764 / week

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from $162 / night

24

Vacation villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Here's a vacation home that has everything you ever wanted in your own home...Big Refreshing Pool...over sized bubbling spa....lots of room for everyone to relax and unwind. Our Home is the ultimate paradise for a Disney holiday which has to be experienced to b  …see more

from $108 / night

$750 - $927 / week

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from $108 / night

(7) Very Good 

24

Vacation home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 130 mi
  • Swimming pool
Had a major refurbishment completed in last 3 years, including new furniture throughout, new tile flooring throughout, granite work surfaces and new appliances in this 2005 Emerald Island Resort, Kissimmee, pool home. Located 3 miles from Disney World main gate, and eas  …see more

from $208 / night

$1040 - $1582 / week

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from $208 / night

(3) Very Good 

43

Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are situated 5 minutes from Disney & local shops & amenities are just around the corner.Emerald Island is the closest community to the theme parks.Whilst staying in our home you can benefit from all the facilities of Emerald Island Resort, including v  …see more

from $89 / night

$618 - $769 / week

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from $89 / night

(1)  

24

Vacation villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 3 nights min

  • 7 bedrooms
  • Sleeps 16
  • 3 nights min
  • Swimming pool
  • Air conditioning
Here's a vacation home that has everything you ever wanted in your own home...Big Refreshing Pool...oversized bubbling spa....lots of room for everyone to relax and unwind. Our Home is the ultimate paradise for a Disney holiday which has to be experienced to be  …see more

from $177 / night

$1235 - $1588 / week

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from $177 / night

20

Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Only 3 miles to Disney, 15 miles to SeaWorld, 17 miles to Universal Studio and has easy access to all major theme parks. This beautiful villa locates in the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded gate. This villa has 8 bedrooms 4.5 ba  …see more

from $351 / night

$1600 - $3189 / week

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from $351 / night

(4) Excellent 

98

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 96 mi
  • Swimming pool
  • Child friendly
In our house, fell like you are at home, with the comfort of a King suit and an attached bathroom with garden tub and 3 more bed : queen bed and fully attached bathroom and kids rooms with 2 twin beds in each and their own bathroom to share. Enjoy the heated swimming po  …see more

from $100 / night

$701 - $1260 / week

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from $100 / night

23

Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
For those looking for the ultimate vacation rental experience, this is the right villa! Located in the tropical grounds of Emerald Island Resort near Disney World, this huge 7 bed villa villa offers outstanding amenities at affordable prices for parties of up to 16 gues  …see more

from $225 / night

$1500 - $2800 / week

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from $225 / night

(7) Excellent 

48

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
A 6 bed/5.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned game room and a south-facing pool/spa.With 4 king master suites and 2 themed kids rooms, this villa can accommodate up to 14 in sheer luxury. The large pool  …see more

from $240 / night

$1700 - $2800 / week

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from $240 / night

(1) Excellent 

20

Vacation villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Only 3 miles to Disney, 15 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, shipping center, restaurants, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful com  …see more

from $300 / night

$1300 - $2639 / week

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from $300 / night

(3) Very Good 

12

Vacation home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Living Room2 and 3 seat sofa's with coffee table ,40" flat screen TV with DVD / BLURAY player. Ceiling fan.Dining AreaTable and 4 chairs KitchenFully equipped with all the utensils you will ever need.Utility RoomFull lau  …see more

from $63 / night

$882 / week

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from $63 / night

28

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Emerald Island Resort is surrounded by a conservation area and encompasses over 300 acres with 11 heavily wooded acres right in the middle of the community. As you pass through the 24 hour guarded gatehouse the playful dolphin fountains welcome you to this unique resort  …see more

from $234 / night

$1638 - $1827 / week

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from $234 / night

(5) Very Good 

22

Vacation villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We offer a beautifully furnished villa on Lido Key Drive. It is 1935 Sq ft and has 4 bedrooms 3 bathrooms.A south westerly facing extended pool deck with raised spa and childs safety fence, the pool deck is 40' x 21' with the pool being 26' x 12&  …see more

from $114 / night

$794 - $1053 / week

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from $114 / night

(2) Excellent 

100

Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 5 nights min

  • 7 bedrooms
  • Sleeps 16
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 120 mi
  • Swimming pool
Golden Palms is a luxury villa of the highest quality in Orlando, Florida. The villa is well appointed with fine furniture and fully air conditioned with additional ceiling fans through out. With a large South facing pool and spa Golden Palms is the perfect holiday home  …see more

from $234 / night

$1632 / week

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from $234 / night

23

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
Our Spacious 8 bedroom pool/spa villa is located at prestigious Emerald Island Resort, a gated community with 24/7 security guard at gate and only 3 miles away from World Disney. Emerald Island Resort featured with its own clubhouse sauna, fitness center, video games ar  …see more

from $351 / night

$1600 - $3189 / week

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from $351 / night

(2) Very Good 

38

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
Pamper yourself in this luxury Emerald Island Resort villa near Disney World. Offering outstanding amenities at affordable prices, this luxury villa with private south-facing pool and spa accommodates 14 guests in sheer comfort and luxury in 6 bedrooms. Like none other  …see more

from $225 / night

$2301 - $2800 / week

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from $225 / night

8

Townhouse rental in Kissimmee with golf nearby

Kissimmee / Emerald Isle Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our Emerald Island Townhouse has a prime location within the resort, right infront of the heated pool and spa, with plenty of chairs and sun loungers to relax on after a busy day in the parks. Also close by are the tennis courts and a childrens play area. The ho  …see more

from $96 / night

$600 - $875 / week

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from $96 / night

(2) Very Good 

100

Vacation villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Secret Key Cove VillaSecret Key Cove VillaNow with direct secure booking and instant confirmationOur beautiful Orlando vacation Villa rental, with many upgrades is a fabulous holiday rental home with private pool, is set in the peaceful and tranquil loca  …see more

from $140 / night

$981 - $1422 / week

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from $140 / night

(3) Very Good 

19

Villa rental in Kissimmee with swimming pool

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 5 bed villa is located in the sought after resort of Emerald Island. It appeals to visitors because it is so close to Disney and it has a lively Clubhouse. Here you find the community pool, tikki bar, fitness and theatre rooms. The home itself is on one level and h  …see more

from $120 / night

$838 - $1235 / week

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from $120 / night

(2) Good 

30

Vacation villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
HI SPEED INTERNET,POOL/SPA EXT/DECKING,GAMESROOM,THEMED BEDROOMS,FREE USA CALLSWelcome to our family Florida Villa a Beautiful 4 bedroom 3 bathroom Vacation VillaLocated in Orlando's most luxurious 24/7 manned gated community, Emerald Island Resort!!  …see more

from $108 / night

$693 - $832 / week

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from $108 / night

(4) Excellent 

39

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
A 7 bed/4.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned theater/game room and a south-facing pool/spa.With 2 king master suites, 2 queen bedrooms, 2 themed kids rooms with two twins each and another room with 2 b  …see more

from $240 / night

$1726 - $2900 / week

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from $240 / night

24

Townhouse rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Our luxurious 1300 sqft, 3 bedroom / 2.5 bath townhouse that sleeps up to 8 is fully air conditioned and very well equipped including a TVs and DVD players in all bedrooms, a PS2 games console for the kids, wireless internet access, free local & national telephone c  …see more

from $111 / night

$701 / week

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from $111 / night

24

Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Only 3 miles to Disney, 14 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded gate.  …see more

from $300 / night

$1300 - $3126 / week

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from $300 / night

(1) Excellent 

20

Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Look no further for your perfect "magic" holiday here at Magic Villa situated within the luxurious Emerald Island Resort. This spacious villa has been refurbished to a luxurious standard, which provides everything you could possibly need for a relaxing, stres  …see more

from $171 / night

$1191 - $1518 / week

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from $171 / night

8

Vacation home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Holiday Lettings Special: Free Pool Heat October through May (Spa heat is always free).Be sure to click the link below to the homeowner's site for more details, a floorplan, more pictures and lots more information. (below where it says 'CLICK HERE - Di  …see more

from $170 / night

$1184 / week

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from $170 / night

(1) Excellent 

84

Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
SKC VillaOur beautiful Orlando vacation Villa rental, with many upgrades is a fabulous holiday rental home with private pool, is set in the peaceful and tranquil location of Emerald Island Resort a gated community. With every possible resort style amenity at  …see more

from $140 / night

$981 - $1422 / week

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from $140 / night

22

Vacation townhouse with shared pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Come and stay in our lovely Florida holiday home located right on Disney's doorstep. It's located in the stunning Emerald Island resort, a prestigious gated community. It's beautifully decorated, with enough space to comfortably sleep 6 people.  …see more

from $76 / night

$567 / week

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from $76 / night

21

Vacation villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Location: Emerald Island Resort, Kissimmee Central West, Kissimmee, Central-Disney-Orlando Area, Florida, USA View MapHI SPEED INTERNET,POOL/SPA EXT/DECKING,GAMESROOM,THEMED BEDROOMS,FREE USA CALLSAccommodations: , 4 Bedrooms, 3 Baths (Sleeps 8)Welco  …see more

from $125 / night

$826 - $1201 / week

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from $125 / night

(24) Excellent 

20

Vacation villa with golf nearby in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
The Luxury, The Home,The Location! The MAGIC is so close you can see the fireworks!! SIMBA'S PRIDE (Sleeps 12 plus infant)Where the magic starts! Family Friendly, 6 Bed, 4.5 bath Villa with Oversize South facing Pool and Spa, 3miles to Disney, Gated/ Gu  …see more

from $200 / night

$1400 - $2001 / week

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from $200 / night

15

Kissimmee Vacation home accommodation

Kissimmee / Emerald Isle Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our Florida home holds so many happy family memories and is very special to us but as we are unable to use it as often we would now like, it is lovely to be able to share it with other families looking to make their own memories. The resort is very well maintained, has  …see more

from $91 / night

$611 / week

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from $91 / night

99

Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 120 mi
  • Swimming pool
Wilderness Lodge is a large premier villa located in the beautiful Emerald Island Resort. It has a south facing private pool plus spa with amazing views over a beautiful lake and woodland conservation area. The Emerald Island Resort is one of the closest to Disney World  …see more

from $189 / night

$1323 / week

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from $189 / night

(2) Excellent 

27

Vacation villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
A 7 bed/4.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned game room and a south-facing pool/spa.With 2 king master suites, 2 queen bedrooms, 2 themed kids rooms with two twins each and another room with 2 bunk beds  …see more

from $225 / night

$2301 - $2800 / week

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from $225 / night

(1) Very Good 

20

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $200 / night

$1400 - $3501 / week

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from $200 / night

(3) Very Good 

48

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 56 mi
  • Swimming pool

 …see more

from $99 / night

$792 - $1400 / week

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from $99 / night

(4) Excellent 

20

Kissimmee / Emerald Isle Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 280 mi
  • Swimming pool
  • Child friendly

 …see more

from $251 / night

$1751 - $2800 / week

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from $251 / night