Orlando Villa Holidays 2026/2027 - Book private pool villas near Disney, flights included

Orlando Villa Holidays 2026/2027 - Book private pool villas near Disney, flights included

Charter Travel is one of the UK's most trusted Orlando Villa Holiday Specialists, established in 1988 and rated 4.9 Excellent on Trustpilot. As a fully ABTA and ATOL protected travel agent / tour operator, we offer complete financial protection on every booking. Orlando Villa holidays from £995 per person. 

Orlando Villa Holiday packages include flights with airlines such as Virgin Atlantic, British Airways, Aer Lingus, Delta Airlines and more. We can also organise other elements of your Florida Holiday including car hire, theme park tickets to Walt Disney World and Universal Orlando Resort, and more. Your personal travel specialist knows Orlando inside and out and will create a tailor-made package to help make your holiday unforgettable. Book your 2026 / 2027 Orlando Villa Holiday with a low deposit today. Orlando Villa Holidays for 2028 are now also available to book!

Why book with Charter Travel

When it comes to booking in Orlando Villa Holiday from the UK, choosing the right travel agent makes all the difference. Charter Travel have been arranging Florida Holidays since 1988, and our team has personally visited every villa resort we offer. Meaning we can advise you on exactly which communities’, budget and travel dates will work for your family.

Charter Travel regularly negotiates exclusive rates with villa owners across Orlando’s most popular resort communities. Orlando Villa Holiday Packages are be tailor-made to suit your budget and requirements. Travelling during off peak periods such as January, May, and September can reduce cost significantly, and opting for a smaller villa or condo during peak dates like the Easter and Summer School Holidays are great way to save money.

Rated Excellent on Trustpilot

Thousands of families have trusted Charter Travel with their Orlando Villa Holidays and shared their experience on Trustpilot. Read independent reviews on Trustpilot on why you should book with us for your next Orlando Villa Holiday.

Fully ABTA and ATOL protected - Your money is 100% safe

Every Orlando villa holiday we sell is fully protected by both ABTA and ATOL, this means you can book your holiday with total confidence.

Exact Villas – No ‘Allocated on Arrival’

Charter Travel only books exact villas, never ‘Allocated on Arrival’. Your personal travel specialist will show you a variety of Orlando Villas to choose from, so you know exactly which property will be staying in for your holiday. Our team works directly with villa owners across Orlando’s most popular resort communities (including the ever-popular Windsor Hills, Emerald Island and Windsor Palms Resorts) to bring you the best villas possible.

Everything in One Package – Flights, Car Hire, Villas, Theme Park Tickets

We organise your entire Orlando Villa Holiday package with flights, car hire, your chosen villa, Walt Disney World and Universal Orlando Resort theme park tickets, and any other extras you want. We want your booking process to be stress free, so you can focus on what's important - enjoying your holiday!

Get Your Orlando Villa Holiday Quote

Tell us your preferred dates, passengers and departure airport and our Florida specialists will check live prices and availability.

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Book and Save on your Orlando Villa Holiday

Flights + Car + Villa Packages

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Orlando Villa Holiday Deals – Best Prices for 2026 and 2027

November Orlando Villa Holiday
November Orlando Villa Holiday
 Quote CHH582
 4 bedroom Orlando villa with own pool, close to all attractions
 Selected travel dates November 2026
 Based on 4 Adults & 4 Children
Direct return flights
from £995 pp
February 1/2 Term 2027 Orlando Villa Holiday
February 1/2 Term 2027 Orlando Villa Holiday
 Quote CHH584
 10 nights in a 5-Bed Named Villa Paradise Palms
 Based on 18 February 2027
 4 adults & 4 children
Return flights to Orlando
from £1155 pp
March 2027 Orlando Villa Holiday
March 2027 Orlando Villa Holiday
 Quote CHH585
 10 nights in a 5-Bed Orlando Villa on Solara Resort
 Travelling 3 March 2027
 4 Adults & 4 Children
Return flights to Orlando
from £1395 pp
7 nights Margaritaville Resort Orlando Cottage Holiday
7 nights Margaritaville Resort Orlando Cottage Holiday
 Quote CHH1147
 Return flights to Orlando
 Travelling selected dates 2026
 4 adults & 2 children sharing
4 Bedroom Cottage
from £1195 pp
2026 Orlando Villa and Universal Helios Grand Hotel
2026 Orlando Villa and Universal Helios Grand Hotel
 Quote CHH1689
 10-nights 4-bedroom Orlando Villa
 Selected dates 2026
 2 adults 2 children
Return flights
from £1766 pp

Popular Orlando Villa Resorts

Emerald Island Resort

Emerald Island Resort

3-7
2-7
4-16

Emerald Island Resort is an Orlando Villa Resort close to Walt Disney World with a large spacious clubhouse. Book your Orlando flights & villa holiday package for 2026. Location is key and this resort is an oasis in the heart of Orlando, offering 4 bedroom villas to larger 7 bed homes

Windsor Hills Resort

Windsor Hills Resort

3-7
2-5
2-16

Windsor Hills Resort is a beautiful gated community close to Orlando’s famous theme parks. Windsor Hills offers comfortable 3 bedroom condos and town homes along with spacious 4, 5 and 6-bedroom villa with private pools - perfect for groups and families! 

Windsor Palms Resort Orlando

Windsor Palms Resort Orlando

3-6
2-4
2-12

Book Windsor Palms for your Orlando Villa Holiday! Stay close to Walt Disney World in a large villa with private pool and communal facilities. Book your flights and villa holiday- ABTA and ATOL Protected.

Champions Gate Resort

Champions Gate Resort

3-9
3-5
6-21

Simply stunning with world-class amenities and unique villas. The resort also features a huge resort-style pool with water slides, lazy river, splash park, state-of-the-art fitness center, tiki bar and movie theatre along with a playground and volleyball courts.

Solterra Resort

Solterra Resort

4-7
3-5
2-14

Luxury villas 4 to 8 bedroom excellently located in a central position for all the major Orlando attractions with excellent resort amenities and spacious villas. 

Storey Lake Resort

Storey Lake Resort

3-9
2-6
2-21

The resort is located in Kissimmee with easy access to Orlando’s major attractions, dining, and shopping areas. Storey Lake has 3 and 5 bedroom town homes and 5-9 bedroom private pool homes.



Orlando Villa Holidays FAQs

Orlando Villa Holidays vs Hotels, which is right for your family?

Many UK families visiting Orlando for the first time ask whether they should stay in a villa, offsite hotel or a Disney / Universal Hotel. Both Disney and Universal offer onsite hotels but staying off-site can significantly reduce costs for your Orlando holiday. Staying in an Orlando Villa gives you private space, your own pool, full kitchen, multiple bedrooms, and plenty of space to relax. For families with young children and multi-generational groups, a villa holiday can offer better value and more relaxed experience.

Car Hire and Orlando Villa Holidays

When booking an Orlando villa holiday, we strongly recommend hiring a car for the duration of your holiday. Orlando villa resorts are located around Walt Disney World but Orlando is not a very walkable area and the car is strongly recommended to ensure you have the freedom to explore and visit the theme parks as you wish

Which Orlando Villa Resort is best for families with young children?

For families with younger children, we most often recommend Windsor Island Resort, Emerald Island Resort or Storey Lake Resort. All three of these resorts offer gated security, communal pools great for toddlers and young children, and short drives to Walt Disney World. Windsor Island Resort has one of the most impressive water park style amenities of any Orlando Villa Resort community, making ideal for families who want resort-style facilities along with their own private villa and pool

Where is the best place to book an Orlando Villa Holiday from the UK?

Charter Travel is a UK based, ABTA and ATOL protected travel agency/ tour operator specialising in Orlando Villa Holidays since 1988. When you book with Charter Travel, not only is your money fully protected and guaranteed but we can book everything in one package holiday. You also get a personal travel advisor who will give you expert tips and tricks to ensure you have the best Florida holiday possible.

Why should I book my Orlando Villa Holiday with Charter Travel?

Charter Travel is consistently rated as one of the UK's leading Orlando Villa specialists with a 4.9 excellent rating on Trustpilot. We do not book ‘Allocated on Arrival’ villas, so you choose your exact villa before you even leave the UK. All packages include flights, car hire, villa, theme park tickets and any extras you require (unless unwanted). Our travel advisors have genuine personal experience with every resort we recommend and book, and you deal with the same advisor from enquiry to returning home. Plus, your advisor will be on hand to answer any questions that you may have

How do I find best deals on Orlando Villa Holidays?

The best Orlando Villa Holiday deals are typically available when you book early, ideally 12-18 months before travel. The cheapest Orlando Villa Holidays will be during January, June, early May, September and early October as these are off peak travel dates for Orlando. Our prices on our website are just a sample of what we can offer, for live pricing and availability please get in touch by calling us on 01635 551011 or filling in our online enquiry form.

Are Charter Travel Orlando Villa Holidays ABTA and ATOL protected?

Yes every holiday package booked with us is fully protected by both ABTA and ATOL.

Are Orlando Villas cheaper than staying in a Disney or Universal hotel?

In most cases, yes, especially for larger families or groups. The cost of an Orlando Villa Holiday with Charter Travel depends on factors such as the villa size, length of stay, and number of guests. However, villas often offer much better value than traditional hotel accommodation because the cost can be shared among more people. Most Orlando, Disney, and Universal hotels typically accommodate up to four guests (two adults and two children), whereas Orlando Villas range from four to nine bedrooms and can comfortably sleep between 8 and 18 people. This allows larger groups to split the overall cost, making it a more affordable option. Villas also come with fully equipped kitchens, giving you the flexibility to prepare meals rather than dining out every night. Over a 10 to 14-night stay, these savings can add up significantly, making a villa holiday an excellent value-for-money choice.

Why Book an Orlando Villa

Benefits of Orlando Villa Holidays

Location

We work with a number of Orlando Villa owners in Florida, meaning you will be able to carefully select where you want to stay. You might want a villa close to Walt Disney World for example on Emerald Island Resort, or a villa close to Universal Studios Florida, for example Vista Cay Resort. Perhaps, on your 2026/2027 Orlando Villa holiday you want to stay a bit further out from central Orlando, but still near all the major attractions, in Davenport’s Providence or Aviana Resorts. When booking your Orlando villa holiday in 2026/2027 your options are endless.

Space

One of the main benefits of booking an Orlando Villa holiday is the abundance of space you will have on your 2026/2027 Orlando holiday. In an Orlando Villa you will have your own private pool, large kitchen, large living area, multiple bedrooms, game room, driveway for parking and much more. There is plenty of space for the whole family to enjoy.

Orlando Villa Facilities

Unlike a regular hotel room, your Orlando Villa will come equipped with a full service kitchen, laundry facilities like a washing machine and dryer, a large living room, and anything else you can think of to enjoy a home-away-from-home holiday in Orlando in 2026/2027.

Resort-like Facilities and Amenities

There are a number of Orlando Villa resorts that also offer guests extra amenities including a large communal pool, pool bar, fitness facilities, game rooms, and more. Favourite resorts in Orlando for these extra resort like amenities are Windsor Palms, Storey Lake Resort, Windsor Island, Emerald Island, Champions Gate and more. Some Orlando Villa resorts even come with their own water park facilities, for example Encore Resort at Reunion, Windsor Hills Resort, Solterra Resort and more.

Free Parking

There is no greater perk in Orlando than free parking! On your Orlando Villa holiday in 2026/2027 you will not need to pay parking fees as your Orlando Villa will come with its own driveway, and town houses feature complementary street parking.

Private Pool

In your Orlando Villa, you will be able to enjoy your own private pool or plunge pool! You will have plenty of space to stretch out on the terrace area surrounding your pool, maybe even cook a BBQ or two! During the winter months, you may want to heat your own Orlando Villa pool- this is something that may be able to be pre-purchased when booking your 2026/2027 Orlando Villa holiday. Speak to one of our specialist Travel Advisors about booking pool heating with your Orlando Villa.

Cost of an Orlando Villa Holiday

Why an Orlando Villa is more cost effective

When you book an Orlando Villa for your 2026/2027 Orlando holiday, it often becomes cheaper as you will be able to split the cost between multiple guests. It is the perfect way for groups of friends or even multi-generational families (grandparents, parents, children) to enjoy a more affordable Orlando holiday in 2026 as you'll be splitting the cost between you.

Cheapest Orlando Villa Resorts

The cost of an Orlando Villa holiday can vary depending on what time of year you travel, for example travelling in off-peak seasons such as January, May, September and early October will often result in a cheaper Orlando Villa holiday. However, there are other ways of keeping your Orlando Villa holiday costs down. For example, for a cheaper Orlando Villa holiday why not consider an Orlando Villa Resort community without large communal facilities such as Crescent Lakes Resort and/or Indian Creek Resort. You will still benefit from all of the Orlando Villa amenities you are expecting such as a private pool, large kitchen, multiple bedrooms, spacious living area, parking, and more, except you may not have a large list of communal facilities – however, for many travellers this is not an issue, so this is a great way to keep your Orlando Villa holiday cost down.

Luxury Orlando Villa Holidays

Orlando Villa holidays and luxury holidays go hand in hand, there are many Orlando Villa resorts that offer a luxury holiday. Reunion Resort is the epitome of luxury; it offers a 5-acre water park, championship golf course, 7 restaurants, and shuttle services to Walt Disney World. Many of the Reunion Resort Orlando Villas back onto the golf course offering a stunning backdrop on those pool days, there are even Reunion Resort Villas that offer in-home movie theatre experiences or the ultimate luxury stay. Of course, there are plenty of other Orlando Villa Resorts that offer guests a luxury experience; Champions Gate Resort is an excellent luxury Orlando Villa holiday option that offers a championship golf course, water slides, and excellently designed villas. Another luxury Orlando Villa resort option is Providence Resort - this Orlando Villa resort offers large and spacious villas with a clubhouse, fitness centre, communal pool, and fantastic golf course.

Orlando Villa Resorts: Our Top Picks

Emerald Island Resort

Emerald Island Resort is one of the original Orlando Villa Resorts, however it is still one of our absolute favourites. Located just five miles from Walt Disney World, Emerald Island Resort offers everything you need to have a fantastic Orlando Villa holiday in 2026/2027. Not only is Walt Disney World just a few moments away, located just a short drive from Emerald Island is the all-new Sunset Walk with many restaurants including Ford's Garage and The Wharf. There is also shopping and a cinema at Sunset Walk. In Emerald Island Resort you will find great communal facilities including a tiki bar, fitness room, communal pool and lounging area- plus a mini golf putting green! Emerald Island Resort offers everything from three bedroom town homes to large seven bedroom Orlando Villas with their own private pools, therefore it has something for everyone which is why we love this resort so much for your Orlando Villa holiday in 2026/2027.

Windsor Island Resort

Windsor Island Resort is one of Orlando’s newest Orlando Villa resort communities, and offers some of the best facilities of all the Orlando Villa resorts. Windsor Island Resort is home to fantastic town homes and Orlando Villas that cater to families of all sizes, plus a stunning clubhouse with an arcade, fitness centre, playground, mini golf, zero entry pool, lazy river, children’s splash pad and water slides! Whatever you are looking for on your 2026/2027 Orlando Villa holiday, Windsor Island Resort has it all! There are also a variety of things to do in the surrounding Kissimmee area; Enjoy the Florida malls, dine out at the huge selection of restaurants, and visit the nearby Walt Disney World and Universal Studios.

Windsor Hills Resort

Windsor Hills Resort is a firm favourite of everyone who visits Orlando Florida, and is a great option for your 2026/2027 Orlando Villa holiday. Windsor Hills Resort features everything from three bedroom condos and town homes up to six bedroom Orlando Villas with large private pools. You will also be just a short drive away from favourites Walt Disney World Resort and Universal Orlando, but also attractions on International Drive like ICON Park. There are also an array of communal facilities to enjoy including a clubhouse, resort style pool with water slide, children's playground, fitness centre, tennis courts, movie theatre and more.

Champions Gate Resort

Champions Gate Resort is beloved by all who visit, and it offers a fantastic array of Orlando Villas and resort amenities for your 2026/2027 Orlando Villa holiday. The resort offers everything from 9-bedroom Orlando Villas two smaller 4-bedroom Villas perfect for smaller families visiting Orlando. The resort also offers water slides, a lazy river, fitness centre, tiki bar, movie theatre, and resort style pool for you to enjoy. You will also be staying just minutes from Walt Disney World at Champions Gate Orlando Villa resort.

Car Hire & Orlando Villas

Theme Parks

When staying in Orlando Villa resort, you will need to hire a car on your Orlando holiday to enjoy Orlando’s theme parks (like Walt Disney World and Universal Resort) to the fullest. Some visitors to Orlando like to use the Orlando Villa resort shuttle buses (if they have them) or take their chances with public transport such as Ubers or pre-arranged taxis, however hiring a car on your Orlando Villa holiday gives you the ultimate amount of flexibility and freedom to come and go as you please to both the Orlando theme parks and your Orlando Villa. Plus, you will not need to worry about paying for parking on your Orlando Villa holiday as Orlando Villas offer plenty of parking space.

Dining Out

Hiring a car for your Orlando Villa holiday in 2026/2027 also means you will be able to dine out at nearby restaurants- this offers you so much more choice for when it comes to dining on your Orlando Villa holiday. Why not try the restaurants on offer at Disney Springs, for example The Edison or the T-Rex Cafe. Or try local Orlando restaurants including Millers Ale House, Ford’s Garage, Olive Garden, and much more.

Food Shopping

Orlando Villa holidays are self-catered holidays, meaning you need to visit local supermarkets like Walmart, Publix, Aldi to purchase food and drink to enjoy in your Orlando Villa. Many families find visiting the Orlando Supermarkets part of the fun of their Orlando holiday; like in the UK there are a variety of supermarkets on offer, and they all offer different prices for different items. Walmart is an American favourite and known by many visitors before they arrive, however a top saving tip from us is to visit Aldi whilst on your Orlando Villa holiday to do your food shopping as comparatively the prices are often much lower.

Your Holiday

Tailor-made to suit your requirements
Proud to work with all major airlines
Constantly recommended as unbeatable on service and value

Expert knowledge

Dedicated destination specialist
Speak to the same travel advisor throughout
Working with local tourist boards and destination managements

Trusted

Established since 1988
FCDO travel aware
24/7 emergency UK support
Award Winning

Fully Protected

You and your holiday are in safe hands with us so you can book with confidence and travel worry free.
Flight inclusive covered by our ATOL
ABTA and IATA