Villas in Kissimmee and Holiday rentals - Holiday Lettings - Holiday Rentals Kissimmee

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Kissimmee

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15,382 Holiday homes

(45) Excellent 

40

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Holiday To Remember” A perfect exciting, fantastic holiday with all the family. Family of 6. In the last week 7.Quality time with everyone.Extremely a special and magical holiday to remember.The villa was fabulous and very homely.Perfect from start t
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from £90 / night

£545 - £565 / week

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Responds fast!
avg. 1 hour 6 minutes

from £90 / night

(55) Excellent 

Certificate of Excellence

42

Westside holiday villa rental

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Location! Location!” GREAT LOCATION of the Villa 5 minutes to Publix, 7 minutes to Target or Walmart, 15 from Disney, the house itself it is very comfortable and clean, big pool, all we needed for our vacation. If I had to book again I certainly would
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Certificate of Excellence

from £95 / night

£575 - £840 / week

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Responds fast!
avg. 16 minutes

from £95 / night

(24) Excellent 

Certificate of Excellence

12

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £91 / night

£550 - £750 / week

Book View

Responds fast!
avg. 1 hour 33 minutes

from £91 / night

(11) Very Good 

Certificate of Excellence

24

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Comfy home from home” Situated in great location for my husband and myself. We love to be in central 192 and it must be here, so convenient for shopping and eating etc. peaceful community also. Home was comfy, would stay here again. Had a well equip
…see more

Certificate of Excellence

from £75 / night

£525 / week

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Responds fast!
avg. 22 minutes

from £75 / night

12

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

from £75 / night

£525 / week

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from £75 / night

(15) Very Good 

Certificate of Excellence

90

Holiday townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Wonderful vacation rental.” Great place to stay. Close to shopping and parks. House was very clean. Owner and management staff were so nice. Pool was clean and warm Refreshing after a long day at the parks. Would recommend this vacation home to my
…see more

Certificate of Excellence

from £70 / night

£600 - £750 / week

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from £70 / night

(33) Excellent 

24

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“FANTASTIC VILLA.....GREAT COMMUNICATION WITH OWNER” Lovely villa, spacious enough for 8 people and fully equipped. The location is lovely too, very quiet, with regular landscaping and nice views. The villa is approximately 2-3 miles from lots of res
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from £75 / night

£550 - £650 / week

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Responds fast!
avg. 1 hour 24 minutes

from £75 / night

13

Holiday villa rental

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £90 / night

£630 / week

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Responds fast!
avg. 38 minutes

from £90 / night

(3) Excellent 

103

Kissimmee holiday villa accommodation

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool

from £133 / night

£925 / week

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Responds fast!
avg. 3 hours 5 minutes

from £133 / night

(16) Very Good 

Certificate of Excellence

40

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Merry christmas” We enjoyed our first ever family vacation over the holiday. The house was beautiful and very close to everything. It was a stress free stay and look forward to staying at this home in the future.
…see more

Certificate of Excellence

from £100 / night

£679 / week

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from £100 / night

(8) Excellent 

21

Trafalgar Village holiday home rental

Kissimmee / Trafalgar Village

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“ideal family villa” The booking of this villa we had a very good service, very helpful with all our questions, nothing was to much trouble very straight forward. The villa was wonderful clean spacious and mordern, it had everything you could need i
…see more

from £108 / night

£825 / week

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from £108 / night

(10) Excellent 

24

Holiday home in Kissimmee

Kissimmee / Tuscany, Florida

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Wonderful holiday in a fantastic Villa!” This was our second family holiday to Orlando so we had an idea of what we were looking for from a villa and a location close to the parks. We considered a number of possible options before settling on Luce Del
…see more

from £115 / night

£815 - £980 / week

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from £115 / night

(40) Very Good 

23

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Great place to stay” Great location really close to Disney parks. Communication with owners was great with lots of information with directions to condo and everything we needed to know while we were staying in the condo. Clean and modern and great ame
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from £53 / night

£245 - £360 / week

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Responds fast!
avg. 3 hours 16 minutes

from £53 / night

(24) Excellent 

21

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“As good as it gets” From the first contact with the owner to our last day at the villa was excellent. The villa décor and facilities were just what we hoped for and more. From our location it was only a short trip to the theme parks eating out or shop
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from £79 / night

£550 / week

Enquire View

from £79 / night

(15) Excellent 

30

Kissimmee holiday villa rental

Kissimmee / Windsor Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Everything you need..and more” Beautiful open plan villa, lots of room, clean, the sofas are really soft and cosy after a day at the parks. The pool was a definate hit with the kids, as was the games room. The gated community was very friendly and h
…see more

from £96 / night

£650 - £700 / week

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Responds fast!
avg. 3 hours 12 minutes

from £96 / night

(24) Excellent 

23

Kissimmee holiday villa let

Kissimmee / Bellavida Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fabulous!” 2nd visit to 'Belleair' Villa at the lovely Bella Vida Resort. We enjoyed our stay so much the first time that we returned again this year! Fabulous, spacious accommodation (seven of us this year and eight last year) with quality furnishin
…see more

from £149 / night

£1,045 - £1,495 / week

Enquire View

from £149 / night

(13) Excellent 

28

Holiday villa in Kissimmee

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £130 / night

£910 - £1,200 / week

Enquire View

from £130 / night

(68) Excellent 

60

Villa rental in Kissimmee

Kissimmee / Indian Ridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent Location and a Wonderful Home.” Never booked through holiday lettings before so I was a bit nervous however I needn't have been. From the first moment I had contact with the owners of Russel Ridge communications and reassurance have been exc
…see more

from £90 / night

£500 - £725 / week

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from £90 / night

30

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £80 / night

£554 / week

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from £80 / night

(19) Excellent 

Certificate of Excellence

49

Bungalow rental in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Family friendly vacation home with screened in pool...immaculate and exactly as posted!” The home was very clean and had a fully functional and equipped kitchen. The bedrooms were each spacious and had sufficient linens. There is wi-fi and sufficien
…see more

Certificate of Excellence

from £83 / night

£518 - £590 / week

Book View

Responds fast!
avg. 58 minutes

from £83 / night

(4) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Tuscany, Florida

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £54 / night

£380 / week

Book View

from £54 / night

(42) Very Good 

20

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing property!” This property really is as amazing as the photos show! Andy offers great communication before, during and after the stay, and it really is a fantastic place to stay. We visited Universal Studios and Wet'n'Wild and it's about a 20
…see more

from £80 / night

£500 - £550 / week

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from £80 / night

(22) Excellent 

24

Holiday villa letting

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Wonderful” The house was perfect size . It had everything you could need for the stay. The pool was great! Game room kept the kiddos busy during our down time. Perfect distance from everything like the theme parks. We went to universal studios. than
…see more

from £72 / night

£483 - £643 / week

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from £72 / night

(16) Excellent 

18

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Golfers paradise” What a lovely place to stay. It was home from home. As we play golf every other day it is somewhere to completely relax on our day off. Slightly too large for two but it was so spacious and relaxing it didn't matter to us. Hopefully
…see more

from £90 / night

£495 / week

Enquire View

from £90 / night

(7) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Country Creek

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £80 / night

£525 - £650 / week

Book View

from £80 / night

(18) Excellent 

20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £85 / night

£595 - £735 / week

Book View

from £85 / night

(31) Very Good 

Certificate of Excellence

36

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £75 / night

£500 - £600 / week

Book View

from £75 / night

(5) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Kissimmee / Lindfields

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £87 / night

£609 - £665 / week

Book View

Responds fast!
avg. 38 minutes

from £87 / night

(28) Very Good 

25

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just Perfect” My wife and I are regular visitors to the Orlando area and have stayed in several Rental Villas in the past. It was our first time at ‘Ventura Villa’ hopefully not our last, we had a really enjoyable stay. The villa is clean, well fur
…see more

from £80 / night

£525 - £1,054 / week

Book View

from £80 / night

(14) Excellent 

Certificate of Excellence

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £130 / night

£910 / week

Book View

Responds fast!
avg. 52 minutes

from £130 / night

(14) Excellent 

Certificate of Excellence

22

Kissimmee holiday villa let

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Super Villa in a super location,” A perfect location for us just a couple of minutes from Kissimmee, Everything you need is there, pool, hot tub, games room, WiFi and as it's English owned it even has a kettle ! (Most Florida Villas don't). Clear i
…see more

Certificate of Excellence

from £85 / night

£595 / week

Book View

from £85 / night

(9) Excellent 

Certificate of Excellence

20

Kissimmee holiday villa rental

Kissimmee / Oak Island Cove

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Super villa” Great for all age groups - has everything you would ever need - teenagers loved the table tennis plus pool. 8 month old grandaughter had cot, toys high hair. The villa is close to shops & theme parks. Quiet estate with villa overlooking l
…see more

Certificate of Excellence

from £100 / night

£700 - £875 / week

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from £100 / night

(6) Very Good 

75

Kissimmee holiday villa let

Kissimmee / Cumbrian Lakes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £85 / night

£595 - £840 / week

Book View

Responds fast!
avg. 38 minutes

from £85 / night

(88) Excellent 

Certificate of Excellence

22

Holiday villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Nice condo to stay with a family” Everything about this condo was accurate based on Debbie's description and previous reviews. Upon arriving, the binders with everything you need to know about the condo and the surrounding area were very helpful. Th
…see more

Certificate of Excellence

from £70 / night

£485 - £600 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from £70 / night

(28) Very Good 

18

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect Family Villa” Great location within easy reach of all attractions including Clearwater and Kennedy Space Centre. Well equipped with comfortable bedrooms and lovely well maintained pool. Perfect villa for having those vital rest and relax days
…see more

from £75 / night

£495 - £595 / week

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Responds fast!
avg. 1 hour 59 minutes

from £75 / night

(17) Excellent 

28

Kissimmee holiday villa rental

Kissimmee / Veranda Palms

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
“Perfect Villa” The villa was incredible. Big and spacious rooms, pool was great, games room was great, and had all amenities we needed.It is in a perfect location for Disney parks (15 mins), universal parks (20 mins), international drive (20 mins) and
…see more

from £95 / night

£650 - £800 / week

Book View

from £95 / night

(42) Excellent 

Certificate of Excellence

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“A beautiful home in the sun.” We stayed in this lovely villa for two weeks and we honestly could not fault it. The location is very good with easy access to Disney plus the i4 and the 192. There is a Walmart under 2 miles away and a number of great re
…see more

Certificate of Excellence

from £90 / night

£630 - £770 / week

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Responds fast!
avg. 21 minutes

from £90 / night

(7) Excellent 

26

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 £105 / night

£550 - £670 / week

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from £105 / night

(20) Excellent 

23

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Really lovely villa” I would throughly recommend this villa,it is truly a great place to stay,very well equipped, and very clean throughout the owner Rose is very helpful with any questions, and is one of the nicest people I have had the pleasure
…see more

from £75 / night

£495 - £595 / week

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Responds fast!
avg. 1 hour 24 minutes

from £75 / night

(35) Excellent 

Certificate of Excellence

16

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic! Didn't want to leave!” The best vacation, my family ever had. Two small children ages 6yrs. and 4yrs. loved the kiddie pool.
…see more

Certificate of Excellence

from £90 / night

£630 - £662 / week

Book View

Responds fast!
avg. 3 hours 33 minutes

from £90 / night

Top Destination reviews

The Beautiful Life - Family Villa, 6 miles to Disney Pk
Highly recommended - Great place with all you need

Took the family to Disney for a few days in March and found Lee's place on VRBO - first time we use this service. This home is amazing, the whole family loved the pool, hot tub, games room, and overall comfort. Nice quiet neighborhood, tons of restaurants very close by. We went to Magic Kingdom and Animal Kingdom, and both were about 15 minutes away. Special thanks to Lee who was extremely kind and helpful, walking me through the VRBO process as well as providing advice on how to make the best of our Disney visits. Will definitely reach out again next time we plan a Disney trip.see more
The Road to "Mandyville"- Fantastic 3 Bedroom Villa
Honeymoon

Brilliant can't fault it at all, everything you need to hand, recommend this villa plenty of space great … see more
VILLAS AT ISLAND RESORT MINUTES FROM DISNEY
FANTASTIC HOME

me It's a Home away from Home. I had a fantastic stay, fully equipped with everything needed in a home, wish I could have stayed longer. Very close to Disney, many other exciting activities and of course shopping malls and outlets at my finger tips. I had the time of my life in the relaxing beautifully furnished home and would highly recommend to others thinking of going on a holiday. You would definitely enjoy the cozy home, club house with pool and spa. I really had a great time and will definitely be booking for my next trip next year. Thanks Irene. Keep up the good hospitality and quality of your home furniture and appliances. I have already spread the word to my family and friends. Hope you get a lot of future bookings. Good luck for the future.see more
The Perfect 6 Bed Resort Home,
Family Christmas Vacation 2017

The home was lovely. It felt like home away from home. Besides Property Management not answering 2 messages about the pool, everything was beautiful. Thanks for allowing my family into your home … see more
The Florida Pad
Very clean, fuctional and cozy home!

We are 5 person family with teen kids and stayed 5 days in dec-jan in the house. We loved the house, enough room for all of us, very well working wi-fi, all cooking utensils were in good shape etc. The pictures do not give the real picture, we think. Voimme suositella tätä taloa. Sijainti rauhallisella omakotitaloalueella. Lämmitetty uima-allas etc oma piha. Siistiä ja puhdasta.see more
Secret Key Villa for up to 8 guests
Emerald isles

We had a fab villa with heated pool. It was immaculate. Emerald isles is an easy location and is very well maintained … see more