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Kissimmee

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293 Holiday homes

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Travellers going to Kissimmee are booking December dates now. Secure your holiday home today and have the perfect trip.

(1) Excellent 

20

Kissimmee holiday 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
You don't need a magic wand or a secret potion to have a dream holiday of a life time . . . . . . All you need is Magic Villa!!!And as Magic Villa is only 10 minutes' drive from Disney the location is magic too!  …see more

from £135 / night

£945 - £1204 / week

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from £135 / 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
“Very enjoyable stay at Simba's Magic home.” Very enjoyable stay at Simba's Magic home. Dealing with the owner, Sri, was super easy and our group really liked the house. Having stayed in Emerald Island several times, this was the best property we've r  …see more

from £192 / night

£1380 - £2320 / week

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from £192 / night

(1) Excellent 

84

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Skc Villa Luxury Award Winning Vacation villa rental, in Orlando, FloridaSet in a Gated CommunityThis 2 story upgraded Villa has, 4 bedrooms, 3 bathrooms, air conditioning and is set in a private location with its own private pool and spa. The luxury Skc VillaNow with  …see more

from £112 / night

£784 - £1138 / week

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from £112 / night

(21) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Immaculate - delivers above and beyond ..” An immaculate villa, perfectly presented and equipped with everything you could need. Choosing a villa always comes with a little bit of interpretation but Sundown Palm delivered above and beyond the descrip  …see more

from £190 / night

£1330 - £1850 / week

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from £190 / night

(4) Very Good 

22

Holiday villa with swimming pool in USA East Coast

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Florida Jewels - 4 bed 3 bath Luxury Villa on Emerald Island, Games room with pool table Arcade game darts and more, extended south west facing pool with spa, free local national and international landline calls.  …see more

from £90 / night

£630 - £835 / week

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from £90 / night

(2) Very Good 

35

Holiday townhouse rental

Kissimmee / Windsor Hills Resort

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“FANTASTIC!” I would highly recommend this 3 bedroom townhouse with heated pool. It was everything and more when we arrived. The outdoor pool was perfect for the kids and the park in the back yard was great to have them play frisbee and soccer. The loc  …see more

from £86 / night

£600 - £800 / week

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from £86 / night

85

Holiday villa with swimming pool in Kissimmee

Kissimmee / Sunset Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
5 Bedroom south facing lakeside pool villa in Sunset Lakes just a stones throw from Walt Disney World. Very private pool area yet with beautiful lake and sunset views.  …see more

from £95 / night

£665 - £995 / week

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from £95 / night

8

Kissimmee holiday villa rental

Kissimmee / Trafalgar Village

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Easy, friendly booking, very good rates and a fun, peaceful relaxation away from the hustle and bustle of the parks guaranteed.We can boast a remarkable, fast acting local management. A phone call with any problem will be sorted fast.  …see more

from £84 / night

£588 / week

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from £84 / 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
Why stay anwhere else when you can get all this within 5 minutes (3 miles) of Disney World Orlando Florida?  …see more

from £88 / night

£560 / week

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from £88 / night

24

USA East Coast holiday villa rental

Kissimmee / Lake Berkley

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Lake Berkley is a private gated community - a veritable oasis ! Located just off the busy and action packed Highway 192 with its array of shops, entertainment & restaurants, Lake Berkley offers the perfect location for that holiday of a lifetime in the Sunshine Stat  …see more

from £123 / night

£860 / week

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from £123 / night

28

Villa rental in USA East Coast

Kissimmee / Emerald Isle Kissimmee

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Marriott Retreat - one of the closest 24 hour Guarded Gatehouse Resorts - Less than 3 miles from Disney - Luxury Executive Villa - 5 bedroom, 5.5 Bath, with Private Pool (30 x 14ft) & Spa with Extended Pool Deck area - 8ft slate Pool Table- Credit Cards acceptedVi  …see more

from £186 / night

£1300 - £1450 / week

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from £186 / night

(3) Excellent 

100

Kissimmee / Paradise Palms

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 103 km
  • Swimming pool
  • Child friendly

 …see more

from £96 / night

£672 / week

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from £96 / night

(5) Excellent 

43

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic villa and excellent location..” When visiting this fabulous villa I was very impressed with the layout and the pool area, much larger than expected. there was lots of additional equipment in the kitchen area. On arrival we were greeted with  …see more

from £66 / night

£460 - £640 / week

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from £66 / night

(1) Excellent 

24

Holiday villa accommodation

Kissimmee / Formosa Gardens

8 18 1 night min

  • 8 bedrooms
  • Sleeps 18
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
St. George's Manor is the flagship villa of 4 luxurious vacation homes by St. George's Villas - our small, family-run villa rental business. We own all of our villas so we can guarantee you the best service with an unmatched passion for making your holiday the best it c  …see more

from £500 / night

£3480 - £4176 / week

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from £500 / night

(11) Excellent 

31

Kissimmee / Paradise Palms

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £80 / night

£924 / week

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from £80 / night

(2) Excellent 

24

USA East Coast holiday home rental

Kissimmee / Lindfields

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is magnificent, fully furnished and equipped to the highest standards with air conditioning and ceiling fans. It has a master bedroom with an en-suite, 3 further double bedrooms and a main bathroom, towels and bed linen are provided. It has a spacious  …see more

from £61 / night

£425 - £500 / week

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from £61 / night

30

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our luxury 2875 square foot villa is located on the beautiful prestigious community of Terra Verde. This ideal 6 bedroom 5.5 bathroom family home is fully air-conditioned, central heated and sleeps up to 14 people comfortably.  …see more

from £180 / night

£1260 - £1680 / week

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from £180 / night

(3) Average 

48

Kissimmee holiday villa rental

Kissimmee / Indian Creek

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The perfect florida villa” This was our second visit to Florida pearl and yet again it didnt disappoint! It was lovely to be back! Florida pearl is in a fantastic location for visiting all the disney theme parks,just a 5 min drive away. Also close by  …see more

from £90 / night

£630 / week

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from £90 / night

22

Kissimmee holiday villa let

Kissimmee / Lake Berkley

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
to do  …see more

from £85 / night

£595 / week

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from £85 / night

(1) Excellent 

55

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Loved it so much” Just spent 2 weeks in this villa, loved it so much! Many happy memories of a great holiday, we are definitely looking into coming again. Slept 6 more then comfortably and the pool is in a great position, gets a few hours sunlight bu  …see more

from £90 / night

£550 - £785 / week

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from £90 / night

(23) Excellent 

20

Holiday 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 km
  • Swimming pool
  • Child friendly
“You must stay in this Home” We have stayed at Emerald Island Resort on several occasions because we like the closeness of the location to the main attractions and the safety of the gated community with 24 hour security. So, when looking for a property  …see more

from £160 / night

£1120 - £1600 / week

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from £160 / night

(4) Very Good 

100

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful sunsets and a fabulous vacation home” We choose Star Lake View as we were looking for a nice lakeside view as we were not disappointed. The views of the sunset were gorgeous and we loved spotting all the wild birds. The villa was immacula  …see more

from £90 / night

£585 / week

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from £90 / night

(3) Excellent 

42

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Cumbrian Lakes

5 11 4 nights min

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
3 D Cinema room with luxury seating . Pool & Spa privacy Water slide /OUTDOOR TV.Unrivalled games room Wurlitzer JukeboxElectric scooters Playstation 3 consoles .iphone docking stations .BBqBaby/toddler cot/bumpers and safety items Fishing equipmentbikesGames roo  …see more

from £140 / night

£980 / week

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from £140 / night

(3) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
6 beds, 4Bath with 3 master suites, new digital TV set in all bed rooms, a 60" TV in living room, Minutes to Disney World and shopping malls, A great place for family vacation with gated community & forest view. A Child high chair, 3 strollers are available on  …see more

from £128 / night

£904 - £1520 / week

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from £128 / night

(5) Excellent 

31

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Lovely villa in great location” Villa as described clean and modern. Pool heating made water a pleasure to swim in. Owner Marie very helpful and responsive via email. Whilst she is based in England has a friend who came around to help solve a few mino  …see more

from £66 / night

£460 - £630 / week

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from £66 / night

(7) Excellent 

22

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
“Excellent property and very helpful owners” This house is excellent and very well maintained. It had all the amenities / facilities we needed and in good working order. Very comfortable and easy to relax after long days at the theme parks. Julie and M  …see more

from £95 / night

£570 - £630 / week

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from £95 / night

(1) Excellent 

21

USA East Coast holiday villa rental

Kissimmee / Lake Berkley

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
*5 Star Rated Accommodation***Over 34 Guest Reviews*** NO BOOKING FEE ! *24hr Guarded and Gated Resort just minutes from Disney World *5 Person Luxury Hot Tub with coloured perimeter lighting *The BEST view on Lake Berkley **In the Centre of the 14 acre Natural Sprin  …see more

from £175 / night

£1225 / week

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from £175 / night

(28) Very Good 

20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very peaceful area to vacation.” Very nice home with all the amenities needed for your vacation. Close to all Disney adventures and alot to do nearby in Kissimmee. Lots of shopping near home too. Very clean home. Would not think twice about rentin  …see more

from £90 / night

£628 - £720 / week

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from £90 / night

(5) Excellent 

36

Holiday villa with shared pool in Kissimmee

Kissimmee / Sunset Lakes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“An excellent holiday” Our stay at Tina & Andy's villa in Sunset Lakes was excellent. It is in a perfect location being in a gated community close to all amenities such as shops, restaurants and Theme Parks. The Villa is very clean and spacious with  …see more

Pricing unknown

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Pricing unknown

99

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
THE VILLA FOR A LUXURY HOLIDAY! South facing pool plus spa, games room, BBQ and beautiful lake and woodland conservation views. One of the closest to Disney World!  …see more

from £150 / night

£1050 / week

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from £150 / night

21

Holiday 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 £100 / night

£660 - £960 / week

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from £100 / night

(1) Average 

54

Villa rental in Kissimmee with golf nearby

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Luxury 4 bedroom villa with south facing pool and spa. Air conditioned throughout, great location just 5 minutes from Walt Disney World.Indian Ridge is a quiet residential community, yet just minutes from theme parks, shops and restaurants  …see more

from £80 / night

£475 - £675 / week

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from £80 / night

42

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Magical Home in the Perfect Location You'll LOVE! Serendipity at Indian Creek offers you all those extra finishing touches that turn an ordinary home into your very own piece of vacation paradise. ** Totally Private Pool & Hot Tub ** Outdoor Poolside Living Space with  …see more

from £308 / night

£2016 - £2856 / week

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from £308 / night

23

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
This superb luxury vacation pool home with 6 bedrooms, 5.5 bathrooms and straight forward fully inclusive pricing has everything that you could possibly need for the perfect holiday.  …see more

from £125 / night

£875 - £1225 / week

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from £125 / night

(54) Excellent 

23

Holiday villa in USA East Coast

Kissimmee / Crescent Lakes

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beyond our expectations” This was our first villa rental in USA. It exceeded our expectations, a spacious modern villa well appointed, washer , tumble dryer, TV in all rooms, dishwasher, games room with full size pool table, air hockey etc, and a love  …see more

from £90 / night

£575 - £690 / week

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from £90 / night

(1) Excellent 

31

Central Florida / Kissimmee

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £118 / night

£825 / week

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from £118 / night

(10) Excellent 

20

USA East Coast holiday villa rental

Kissimmee / Bellavida Resort

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“5 star villa - everything you need for the holiday of a lifetime” This was our third visit to Orlando and was way beyond our expectations. The villa was amazing. Spacious, luxurious and well equipped with everything you need for a relaxing holiday.  …see more

from £160 / night

£1087 / week

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from £160 / night

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Closest Resort to Disney, one of the closest villa to the Clubhouse. No rear neighbours. Great Park-view from the pool terrace.  …see more

from £148 / night

£1036 / week

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from £148 / night

(3) Very Good 

92

USA East Coast holiday home rental

Kissimmee / Cumbrian Lakes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“This place is amazing” We stayed here for a week after a tiring but fun road trip and as a base station for the theme parks! It was exactly what we needed for a group of 7 friends! Good location for the parks, lovely area and amazing view of the sunse  …see more

from £130 / night

£910 - £1500 / week

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from £130 / night

(5) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home from Home. Great Location. Perfect.” The Villa was everything we dreamed of for our first family holiday in Florida. First impressions were just as we expected, Directions to villa were spot on. Swimming pool was fab with inflatables included. Ho  …see more

from £90 / night

£630 - £665 / week

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from £90 / night

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