5 Bedroom Kissimmee Villas

Search for your perfect Florida holiday villa by availability, number of bedrooms, location and specific requirements. All villas are within a 30-minute drive of Walt Disney World Resort. Where you find suitable villas or want to compare villa amenities, location and price, simply Save to Shortlist.
5 Bedroom Kissimmee Villas
5 bedroom Florida vacation homes although very similar in what they offer to 4 bedroom properties, give you that extra space - especially when you want to bring the mother-in-law along! Whether a single storey or split over two floors, these villas are ideal for two families or a large single party - with a variety of bedroom layouts offering multiple en-suite bedrooms. For guests with limited mobility or requiring wheelchair access, always check with the owner as to whether there is a ground floor bedroom and bathroom. Almost all villas of this size will offer garaged parking or where the space has been converted - a games room.
Where you have searched on specific dates and prices are available, then an estimated price for your dates will be shown. Where no dates are selected, then the lowest nightly rate will be shown. These prices are for renting the villa (not per person) and will include local Florida taxes but will exclude any discounts or optional extras e.g. pool heating.
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#229  Smiths Disney Villa

5 Bedrooms, sleeps 10
• 4 Ensuite and 1 Twin
• 4.5 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Disney Springs 18.5 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling Payment accepted in US Dollars
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From £110 / US$174 per night
This luxury 5 bedroom, 4 bathroom 2830 sq ft Villa is perfect for accommodating extended families sharing 5 star accommodation at very reasonable rates. Features include a private custom shape pool with large sun deck, no rear neighbours, free WIFI, games room, free local and USA calls, BBQ available on request for an additional small daily fee, and essential baby equipment. Only 15 minutes from Disney parks.

Our luxury villa offers...

- 5 bedrooms, 4 en-suite
- Massive patio area with custom shaped private pool & spa with no rear neighbour

#120  Executive 5 Bed Villa in exclusive gated community of The Shire, West Haven

5 Bedrooms, sleeps 10
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Community Clubhouse
• Disney Springs 14.9 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room 360° Video Tour Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £174 / US$235 per night
5 Bed / 4 Bath Executive Home with South Facing Private Pool, Spa and Screened Balcony with No Rear Neighbours in Private Gated Community of The Shire at West Haven 15 Minutes from Disney

Huge 3,221sq ft of indoor living space just 15 minute drive from Disney.


****** SUPERIOR VACATION HOME SLEEPS 10 WITH 5 BEDROOMS AND 4 BATHROOMS ******


2 KING SIZE MASTER BEDROOMS WITH EN-SUITE BATHROOMS
HEATED CHILD FRIENDLY POOL & SPA WITH PRIVATE SOUTH FACING ASPECT AND...

#153  Beautiful Florida holiday home with private south facing pool & spa

5 Bedrooms, sleeps 10
• 2 Ensuite, 1 Double and 2 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Disney Springs 6.9 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £99 / US$153 per night
Beautiful Florida holiday home with private south facing 30’x18’ pool & spa, located in the quiet gated community of The Hamlets. Just off highway 192 in Kissimmee, it is only a few minutes drive to hundreds of shops, restaurants & attractions and some are even within walking distance. Our home is just a short drive to Disney Maingate & Sea World.. The villa is beautifully furnished to the highest standards with themed rooms for children.

We hold a TripAdvisor Certificate of Excellance for 2017, 2018 and 2019

#155  Sunrise Dream, Lakeside Haven, Disney only 4 miles,Hot Tub, Games Room, 2 Master Suite

5 Bedrooms, sleeps 10
• 2 Ensuite, 1 Double and 2 Twin
• 3.5 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Lake Views
• Disney Springs 10.3 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £182 / US$255 per night
Welcome to Villa Sunrise Dream, our fabulous lakeside haven, in Kissimmee, Orlando, Florida.

In a prime location, just 4 miles from Disney World on the stunning gated community of Sunset Lakes (a prestigious, peaceful, gated community), we are close to US192 in the much sought after Formosa area with many shops and restaurants nearby. Villa Sunrise Dream is close enough to the attractions (Disney is less than 10 minutes) to return home for a leisurely lunch and cooling swim during your day . Golfers will be spoilt for choice with numerous superb courses nearby.

#282  Sunset Dream, Lakeside 4 Miles to Disney, Hot Tub, Games Room, 2 Masters

5 Bedrooms, sleeps 10
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Lake Views
• Disney Springs 10.3 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £182 / US$255 per night
Welcome to Villa Sunset Dream, our second fabulous lakeside haven, in Kissimmee, Orlando, Florida.

In a prime location, just 4 miles from Disney World on the stunning gated community of Sunset Lakes (a prestigious, peaceful, gated community), we are close to US192 in the much sought after Formosa area with many shops and restaurants nearby. Villa Sunset Dream is close enough to the attractions (Disney is less than 10 minutes) to return home for a leisurely lunch and cooling swim during your day . Golfers will be spoilt for choice with numerous superb courses nearby.

#485  Spectacular view of Lake Berkley and Island

5 Bedrooms, sleeps 11
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Lake Views
• Community Clubhouse
• Disney Springs 9.3 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling
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From £160 per night
It's all about 'THE VIEW'!!!

We extend a warm invitation to you and your family, to enjoy the delights of our luxurious 5 bedroom (2 en-suite masters), 4 Bathroom Executive Lake View home with the added bonuses of a games room, private screened pool and a lanai.

Our beautiful, spacious and inviting home has been professionally furnished and is comprehensibly equipped with everything that you would require for the perfect vacation - even down to an umbrella! Yes it does sometimes rain in Florida!

Winter Haven enjoys a prime location within Lake Berkley resort,...

#209  Watersong Sunset Villa - Stunning 5 Bedroom Home in Exclusive Gated Resort

5 Bedrooms, sleeps 10
• 3 Ensuite, 1 Double and 1 Twin
• 4.5 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Lake Views
• Community Clubhouse
• Disney Springs 19.0 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £135 / US$185 per night
Welcome to Watersong Sunset Villa where a fabulous vacation awaits. Enjoy the delights of all the Orlando attractions and then relax in the tranquillity and luxury of your own private surroundings.

Situated on the prestigious gated community of Watersong with a 24-hour security guard, our stunning South-West facing villa offers everything you need for the perfect family getaway.

Our fully air-conditioned home is set on an extra-wide plot and, with a huge 3,200 sq ft of living space, 5 bedrooms and 4.5 bathrooms, easily accommodates 10 people, plus a baby. Set...

#339  Luxury 5 Bedroom Pool Villa at the Stunning Watersong Resort

5 Bedrooms, sleeps 10
• 3 Ensuite and 2 Twin
• 4.5 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Community Clubhouse
• Disney Springs 19.0 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Barbecue Grill 360° Video Tour Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £106 / US$146 per night
Fabulous Luxury 5 Bedroom, 4.5 Bathroom Florida Villa with Magnificent 30ft Heated Pool/Spa close to Disney and Orlando attractions.

One of Watersong's most popular, luxury villas, just 15 minutes from Disney

Situated on the lovely Watersong gated Community, our luxurious villa is available for your dream holiday.

Featuring a super extended sun deck, one of the largest at Watersong, backing on to a tranquil conservation area full of Florida nature, and with a lanai to provide shade when you want it.

You will adore the spacious living accommodation, 4K smart...

#139  5 Bedroom villa with south facing extended pool and deck

5 Bedrooms, sleeps 10
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Community Clubhouse
• Disney Springs 9.9 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £135 / US$205 per night
Welcome to our 5 bedroom vacation home located within the upscale, gated community of Emerald Island Resort in sunny Central Florida. Located just 3 miles from the Walt Disney World Main Gate, our home is ideally located for easy access to some of the Worlds best theme parks, award winning dining options and the best in brand-name shopping.

Our home features 5 spacious bedrooms, a spacious family room with direct pool access, a fully equipped kitchen, a generously equipped games room and a large, private swimming pool with spa. Needless to say, our home at Emerald Island...

#144  BrightwaterVilla spacious lakeside home at beautiful gated / guarded Lake Berkley

5 Bedrooms, sleeps 11
• 2 Ensuite, 1 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Lake Views
• Community Clubhouse
• Disney Springs 9.3 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From £165 / US$216 per night
BrightwaterVilla
Our spacious 5 bedroom, 4 bathroom, lakeside home in an oasis of calm off Highway 192 in Kissimmee within walking distance of Medieval Times, WalMart. 7.8 miles to Disney.

We sleep 10 in comfort. 11th guest charged at $25 / £18 per night including taxes. 11th guest is accommodated on a sofabed in upstairs open plan den; or we have 2 travel cots / cribs for infants.

We are baby and toddler friendly. Bed side guard, stair gate, 2 high chairs, 2 good quality reclining buggies / strollers with hoods.

Downstairs and upstairs lake and pool facing...

#443  Superior Villa with Extended Pool and Deck

5 Bedrooms, sleeps 10
• 3 Bathrooms
• Private Pool
• Wi-Fi
• Barbecue
• Community Clubhouse
• Disney Springs 15.3 miles
Private Pool Wi-Fi Internet Barbecue Grill Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Borders Golf Course Payment accepted in Sterling
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From £104 per night
OUR VILLA IS ONLY 10 MINUTES FROM DISNEY

Larger than average fully air conditioned beautiful modern 5 bedroom elegant, contempory executive villa for guests who deserve the very best. EVERYTHING is provided to make your holiday carefree in luxury accommodation.

HIGHLANDS RESERVE is one of the most highly sort out golf communities in the Disney area with a welcoming feel.

The south-west facing 32ft pool with multi coloured lighting backs onto the golf course so is very private. It has soft lighting and luxurious padded patio furniture to enjoy.

#335  5 Bed 5 Bath Villa with South Facing Pool

5 Bedrooms, sleeps 10
• 5 Ensuite
• 5 Bathrooms
• Private Pool
• Wi-Fi
• Community Clubhouse
• Disney Springs 8.0 miles
Private Pool Wi-Fi Internet Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling
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From £123 per night
Stunning 5 bedroom 5 bathroom villa with south facing pool located on Windsor Hills, the closest 5* gated community to Disney

Our 2 storey detached home has all the comforts of home under the glorious Florida sun. Professionally furnished and styled each bedroom has its own identity encouraging a restful nights sleep after a busy day experiencing everything Orlando has to offer.

Located just 3.5 miles from the entrance to Animal Kingdom (there's a short cut to avoid most of the 192 traffic!) Windsor Hills offers a great base from which to explore Walt Disney World...

#407  MickeysDisneyVilla at Champions Gate

5 Bedrooms, sleeps 10
• 2 Ensuite and 3 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Disney Springs 15.7 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Payment accepted in US Dollars
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From US$148 per night
Welcome to our Beautiful 5 bedroom 3 bathroom home called Mickeysdisneyvilla It is in the quiet area called Sandy Ridge in Champions Gate Davenport. 5 minutes off the I-4. Two minutes away from shops Restaurants Banks Etc. 5 minutes away from 3 great golf courses at Champions Gate. Disney Parks and attractions are straight down the I-4 20 minutes drive. 12 MINUTES TO MAGIC KINGDOM - FREE wi fi - TV in all bedrooms - Wii games console ( access to Netflix ) FREE Stroller – FREE High chair – FREE Travel cot - Conservation Area to the Rear and to the left. We have a FLAT...

#261  FANTASTIC 5 bed 4 bath (3 en-suite) Luxury Villa with Private Pool/Spa

★ LATE DEAL ★ — 25 June 2022 - 22 December 2022 — PRICES REDUCED
5 Bedrooms, sleeps 11
• 3 Ensuite and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Disney Springs 14.6 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller 360° Video Tour Shops Nearby Restaurants Nearby Community / Resort Pool Tennis / Sports Courts Payment accepted in Sterling Payment accepted in US Dollars
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From £114 / US$140 per night
Aquilo House is a luxury two-storey detached home situated in the beautifully maintained Hampton Lakes community, just 20 minutes away from Disney World in Florida. The rear of the house faces south, thereby affording all-day sunshine to the pool and patio area. With approximately 3,000 sq ft of living space, the villa is much larger and better appointed than many of the properties offered for holiday rental in the Orlando area. It is fully air conditioned throughout and ceiling fans are fitted in the principle rooms to assist in the circulation of warm and cool air....

#460  Calabay Palms Villa - Calabay Parc (Not Tower Lakes)

5 Bedrooms, sleeps 12
• 1 Ensuite, 1 Double and 3 Twin
• 3.5 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Disney Springs 18.5 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Payment accepted in Sterling
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From £155 per night
​Calabay Palms Villa is a Privately owned Luxury 5 Bedroom, 3.5 Bathroom, Fully Air-Conditioned, with 5* Games Room, South Facing 33' x 12' Private Pool and Hot Tub. Sleeps 12​

​Located within the immaculate and beautiful landscaped gardens of Calabay Parc set in the pine tree and orange grove Highway 27 approximately a five minute drive south from Highway 192 and north to Interstate 4, 35 minutes from Orlando International Airport

Calabay Parc is now firmly established and accepted as one of the most desirable communities for those wishing to...

#431  5 bedroom villa on Sandy Ridge in the Kissimmee/Davenport borders

★ LATE DEAL ★ — 10 March 2022 - 31 December 2024 — Discount for Snowbird stays
5 Bedrooms, sleeps 10
• 3 Double and 2 Twin
• 4 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Lake Views
• Disney Springs 15.7 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Payment accepted in Sterling
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From £136 per night
This is a luxury 5 bedroom 4 bathroom 2 living room double storey villa with own private pool with jacuzzi ( recently resurfaced) on a large corner plot overlooking a small lake. On the conservation area of sandy ridge. We are on the borders of Kissimmee/Davenport just a short drive to ChampionsGate and Interstate 4

#160  SOUTH FACING, 5 BEDROOMS, 3 BATHROOMS, GAMESROOM, KISSIMMEE

★ LATE DEAL ★ — 26 June 2022 - 1 July 2022 — Short Break Deal
5 Bedrooms, sleeps 12
• 1 Ensuite, 3 Double and 1 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Games Room
• Lake Views
• Community Clubhouse
• Disney Springs 9.3 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Games Room Cot and Stroller Shops Nearby Restaurants Nearby Community / Resort Pool Clubhouse Tennis / Sports Courts Gated Community Payment accepted in Sterling Payment accepted in US Dollars
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From £160 / US$233 per night
Welcome to our true south facing villa with stunning, uninterrupted views of the largest lake on Lake Berkley resort. Being one of only seven villas with this south facing view you can be assured when the sun is shining it will be on you, great to relax, enjoy and listen to nature and watch wildlife from the pool deck. If you still want to enjoy the outdoor sun but fancy some shade the lanai is ideal for alfresco dining with picturesque views. The large pool deck hosts a private pool, hot tub and lanai with sun loungers, table and chairs.
The Villa boasts over 3000 ft.²...

#286  Ex Show model 5 Bed Villa not overlooked

5 Bedrooms, sleeps 12
• 2 Ensuite, 1 Double and 2 Twin
• 3 Bathrooms
• Private Pool with Spa / Hot Tub
• Wi-Fi
• Barbecue
• Games Room
• Disney Springs 8.2 miles
Private Pool Spa / Hot Tub Wi-Fi Internet Computer or Laptop Games Room Barbecue Grill Cot and Stroller Wheelchair Accessible Shops Nearby Restaurants Nearby Gated Community Payment accepted in Sterling Payment accepted in US Dollars
Book this villa
From US$171 / £128 per night
Location Location Location
that’s the first thing you need to know about where you want to stay on your vacation
is there shops nearby YES 1 min drive or 5 Min’s walk
is there Restaurants nearby Yes 1 min drive or 5 Min’s walk
is the villa in a private gated community Yes
are there villas overlooking this villa No you have complete privacy
is the villa in a safe area Yes its in the Formosa Gardens area
Shortlisting a is the easiest way to compare specific villas for availability, location, amenities and price. Saving a villa to your shortlist will not contact the owners, so for more information on renting the villa, you still need to send an enquiry.