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The best Orlando vacation homes with private pool are in gated resort communities in Kissimmee and the Reunion area, 15 to 30 minutes by car from Walt Disney World. There, you rent a whole house with its own pool and still get a clubhouse with water slides, a lazy river or a bar. For a family of six or more, or two families traveling together, one home often works better than two or three hotel rooms.
A vacation home is not a hotel with a bigger room, though. Check-in usually happens at a gatehouse or clubhouse, heating the pool can cost extra, homeowners’ association (HOA) rules limit cars and coolers, and fees vary from home to home. This guide compares seven communities whose official pages we checked, and explains what changes when you swap a hotel for a pool home.
Fees and policies change often, so treat every number below as correct at the time of writing and confirm it before you pay.
Quick answer: For the easiest booking, choose Encore Resort at Reunion (every home has a private pool, plus a guests-only water park and theme park shuttles) or Margaritaville Cottages Orlando (its Elite cottages have private pools, and pool heating is included). For the shortest drive to Disney, look at Windsor Hills Resort, where every single-family home has a screened pool with a spa. Storey Lake sits closest to Universal and SeaWorld, while Windsor at Westside and Solara pair pool homes with big clubhouse water areas off US-192.
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How we chose
We kept only communities near Disney with an official source for how they work: the resort operator, the HOA or a rental site endorsed by the community’s management. Then we weighed:
- Private pools: whether the operator says every home has one, or only some, so you know when to filter listings.
- Location: road distance and drive time to the Magic Kingdom parking lot and to Universal, calculated with OSRM routing. These are free-flow estimates, so allow extra time for I-4 and US-192 traffic.
- Shared amenities: clubhouse pools, slides, lazy rivers, dining and shuttles, as stated on official pages.
- Fees and rules: resort fees, pool heating, deposits, parking limits and check-in steps, where they’re published.
We don’t use review scores, and no community paid to be included.
Orlando vacation homes with private pool compared
| Resort | Area | Homes | Private pool | To Magic Kingdom lot |
|---|---|---|---|---|
| Encore Resort at Reunion | Reunion, Kissimmee | 4–13 bedrooms | Every home | About 10 mi, 20 min |
| Windsor Hills Resort | Old Lake Wilson Rd | Condos to 6-bed homes | All homes; townhomes plunge pool | About 9 mi, 15 min |
| Margaritaville Cottages | US-192, Kissimmee | 1–8 bedrooms | Elite and some other cottages | About 9 mi, 17 min |
| Reunion Resort & Golf Club | Reunion, Kissimmee | 3–15-bed homes, villas | Homes (check each) | About 12 mi, 22 min |
| Storey Lake | Kissimmee, east of I-4 | Varies by owner | Varies by home | About 10 mi, 17 min |
| Windsor at Westside | Off US-192 west | 4–9 bedrooms | Pool homes; townhomes vary | About 14 mi, 24 min |
| Solara Resort | Off US-192 west | Varies by owner | Varies by home | About 14 mi, 26 min |
Drive times are OSRM estimates without traffic, from each clubhouse or front desk.
1. Encore Resort at Reunion
Encore is the closest thing to a hotel among Orlando’s pool-home communities. One operator, Rentyl, runs the front desk, the guests-only water park and the restaurants. Its FAQ says every home has a private pool, and homes range from 4 to 13 bedrooms. Not every home has a spa, but you can request one.
The clubhouse at 7635 Fairfax Drive handles check-in. On-site dining includes Finns Restaurant, the Bis Grill, the Shark Lounge and the Encore Coffee House, and there’s a manned entrance gate with security on site around the clock.
- Why stay: a guaranteed private pool at every home, plus a water park only Encore guests can use.
- Getting there / to the parks: Encore says Walt Disney World is about 7 miles or 15 minutes away. Our routing gives about 10 miles and 20 minutes to the Magic Kingdom parking lot, and about 18 miles and 27 minutes to Universal. Theme park shuttles are covered by the resort fee and must be reserved with the concierge. Airport transfers cost extra.
- Good to know: the resort fee varies by home. It covers Wi-Fi, the water park, resort pools, the fitness center, attraction transportation and self-parking. Pool heat costs $40 a night from May through October and $60 a night from November through April. Check-in is at 4 p.m. and check-out at 10 a.m. The lead guest must be 21 or older, and there’s a $500 refundable incidental deposit at check-in.
Best for: big groups who want one booking, a pool at the door and hotel-style services.
2. Windsor Hills Resort
Windsor Hills, at 2600 N Old Lake Wilson Road, is the closest of these communities to Disney. Its official rental site, run on behalf of the Windsor Hills Master Association, says all single-family homes have a private screened pool with a spa, and each townhome has a plunge pool. Single-family homes have 4 to 6 bedrooms, and there are also condos and townhomes. Behind the 24-hour manned gate is a clubhouse with a lagoon-style pool and water slides, a fitness center, a 40-seat movie theater and an arcade.
You book directly with each home’s owner or manager, not with a central front desk. Once you arrive, you pick up free wristbands at the Welcome Center in the clubhouse. Guests need them to use the community pool, hot tub and water park.
- Why stay: the shortest drive to Disney on this list, and a pool with a spa at every single-family home.
- Getting there / to the parks: the resort says it’s 2 miles from Walt Disney World’s gates, which is close to the property line rather than to a park. Our routing gives about 9 miles and 15 minutes to the Magic Kingdom parking lot, and about 16 miles and 25 minutes to Universal. The rental site’s transportation page recommends a car, Uber or Lyft; a paid park shuttle mentioned on its home page may not run, so confirm it.
- Good to know: the community pool and hot tub are open 8 a.m. to 10 p.m., and the pool is heated to 82°F in winter. Slides run 10 a.m. to 8 p.m. from April through September and until 6 p.m. from October through March. RVs, trailers and other oversize vehicles must use a separate lot, and town-home driveways fit one car.
Best for: Disney-focused families who want a full pool home as close to the parks as possible.
Check available homes at Windsor Hills Resort on Booking.com
3. Margaritaville Cottages Orlando
The Margaritaville Cottages are the vacation-home side of Margaritaville Resort Orlando, off US-192 at 8000 Fins Up Circle. They’re rented through Rentyl, and the colorful cottages have one to eight bedrooms. Not every cottage has a pool. The official room pages list a private pool for the Elite cottages from two to eight bedrooms (waterfront in the largest sizes), plus a few other pool cottages, such as the 3-bedroom Water’s Edge Cottage with Pool. Rentyl’s FAQ says pool, spa and hot tub heating is complimentary.
Cottage guests get the same services and resort amenities as hotel guests, including the resort pools and theme park shuttles. For room details and the hotel side of the resort, see our Margaritaville Resort Orlando guide.
- Why stay: pool heating included, a hotel front desk, and dining you can walk to.
- Getting there / to the parks: the resort quotes 10 to 15 minutes to Walt Disney World and 20 to 25 minutes to SeaWorld and Universal. Our routing gives about 9 miles and 17 minutes to the Magic Kingdom lot. Shuttles to the major theme parks are part of the resort fee, and you reserve them with the concierge.
- Good to know: the cottage resort fee rises with size. At the time of writing, the official room pages list $34.40 a night for one bedroom up to $58.50 for eight, included in the rate. Each cottage includes two parking passes. Extra cars pay $20 plus tax a night for self-parking per the resort’s FAQ, or $25 a day per Rentyl’s cottage FAQ, so confirm yours. Check-in is at 4 p.m., check-out is at 11 a.m. and you must be 21 or older. There’s a $50-per-day incidental deposit. Rentyl lists a two-night minimum stay, but the resort’s FAQ says there’s none, so check your terms. Island H2O Water Park is ticketed separately unless your rate says otherwise.
Best for: families who want a pool cottage but still like hotel restaurants, a bar scene and a front desk.
Check your dates for Margaritaville Cottages Orlando on Booking.com (choose an Elite cottage if you want a private pool)
4. Reunion Resort & Golf Club
Reunion is a golf resort with three championship courses designed by Arnold Palmer, Tom Watson and Jack Nicklaus. It has more than 80 rental homes, which Reunion advertises with 3 to 15 bedrooms. Its FAQ says the homes have their own amenities, including private swimming pools, but each home differs, so confirm the pool. Guests also share eight resort pools and a five-acre water park with a lazy river and slides.
The resort also rents one- to three-bedroom villas and tower suites. On Booking.com, Reunion’s own listing shows those villas and suites with water park access, not the pool homes. If you want a private pool, book the home through the resort’s site, or confirm the listing says “private pool.”
- Why stay: a quieter golf setting, a big water park and homes for very large groups.
- Getting there / to the parks: the resort fee includes a scheduled Disney shuttle that drops off at EPCOT or Hollywood Studios, with Disney buses onward. Reserve online up to three days ahead, by 7 p.m. the day before. Reunion runs no shuttle to Universal or SeaWorld. By car, it’s about 12 miles and 22 minutes to the Magic Kingdom lot, or 20 miles and 30 minutes to Universal.
- Good to know: the resort fee is $40 plus tax a night (it may be higher for larger homes), and parking is $20 plus tax a day per unit, with no RV, boat or trailer parking. Pool heating is a daily fee for most homes and can take up to 12 hours to warm up. Check-in is at 4 p.m. and check-out at 10 a.m. Pets aren’t allowed in villas or homes, and water park access depends on how you book.
Best for: golfers and multigenerational groups who want space and a calm, residential feel.
Compare villa and suite rates at Reunion Resort & Golf Club on Booking.com (villas and suites only, not pool homes)
5. Storey Lake Resort
Storey Lake is a resort community in Kissimmee, east of I-4, with two clubhouses. The Hideaway Club has a lazy river, two-story slides (42-inch minimum height), a splash pad, mini golf, kayak rentals and a lakeside hot tub. The Bronson Club adds a second lazy river with a pirate-ship island, an arcade and a gym. Both have a full bar and a kitchen, and an on-property shuttle can take you from your home to either club.
Homes here are rented by many different owners and managers, so a private pool depends on the property. Filter for it, and check whether the listing means a full pool or a small splash pool.
- Why stay: the best location here for splitting time between Disney, Universal and SeaWorld, with two water-play clubhouses.
- Getting there / to the parks: our routing gives about 10 miles and 17 minutes to the Magic Kingdom lot, 12 miles and 20 minutes to Universal, and 9 miles and 18 minutes to SeaWorld. Plan on driving, since the clubhouse shuttle stays on property.
- Good to know: both clubs open at 9 a.m. for the pool and gym, and the Hideaway Club closes at 9 p.m. You need proof of your stay to enter, either the community’s QR code or an email confirmation with your dates and address. Guests under 18 must be with an adult. Outside food, drinks, alcohol, coolers and tumblers aren’t allowed in the clubs.
Best for: families planning both Disney and Universal days who want a pool home in the middle.
6. Windsor at Westside
Windsor at Westside opened in 2015 and was built by Pulte Homes. The HOA’s site describes single-family pool homes and townhomes with 4 to 9 bedrooms. Its 10,000-square-foot clubhouse has a zero-entry pool with a waterslide, a lazy river, a hot tub, a kids’ water playground, a kids’ activity center, a free game room and the Tu Casa Bar and Lounge for poolside food.
To check in, show your booking confirmation and driver’s license at one of three guest gates to get a community access card. At the clubhouse, your party signs a pool waiver once a day.
- Why stay: big homes for large groups and a well-equipped clubhouse.
- Getting there / to the parks: about 14 miles and 24 minutes to the Magic Kingdom lot, and 21 miles and 34 minutes to Universal, by our routing.
- Good to know: the pool is open from 9 a.m. until dusk and the clubhouse from 9 a.m. to 9 p.m. Outside food, drinks and coolers aren’t allowed on the pool deck. Vehicle limits are strict: three cars for townhomes and 4–5-bedroom homes, four for 6–7 bedrooms and five for 8–9 bedrooms. RVs, trailers and boats aren’t allowed, and pet rules are set by each homeowner.
Best for: groups of 10 or more who will drive to the parks and spend downtime at the clubhouse.
7. Solara Resort
Solara is a gated Mattamy Homes community off US-192, at 1575 Carey Palm Circle. The HOA says it’s about 8 miles from the theme parks. Its Grand Clubhouse is open daily from 8 a.m. to 8 p.m. It has a resort pool with cabanas, a zero-entry splash pad and waterslides, the Solstice Bar and Grill, a tiki bar, a fitness center, basketball and beach volleyball courts, and a FlowRider surf simulator.
As at Storey Lake, homes are rented through individual owners and managers, so filter for a private pool.
- Why stay: a standout clubhouse with a surf simulator that teens will actually use.
- Getting there / to the parks: about 14 miles and 26 minutes to the Magic Kingdom lot, and about 22 miles and 36 minutes to Universal, by our routing. You’ll want a car.
- Good to know: the HOA publishes clubhouse hours but not guest fees. Check your listing for cleaning fees, pool heat and the security deposit.
Best for: families with older kids who want an active clubhouse and don’t mind a longer drive.
Vacation homes vs hotels: what changes
A pool home gives you separate bedrooms, a full kitchen and a pool nobody else uses, but a few things work differently:
- Pool heat is often extra: Florida pools can feel cool from roughly November to March. Encore charges $40 to $60 a night, Reunion charges a daily fee for most homes, and Margaritaville’s cottages include it. For other homes, ask the manager for the nightly price and how many hours ahead it must be switched on.
- Fees vary by home: besides the nightly rate, you may see a resort fee, a cleaning fee, a damage deposit or a booking fee. Compare total prices, not nightly rates. Rates vary by season, availability and how far ahead you book.
- Check-in rules: many operators require the lead guest to be 21 or older (Encore and Margaritaville both do). Community gates usually ask for your confirmation and ID.
- HOA rules apply: expect vehicle limits, bans on RVs and trailers, wristbands or waivers at the clubhouse, no coolers on the pool deck and county noise rules (Encore notes that amplified sound must stop by 10 p.m.).
- No daily housekeeping by default: most homes are cleaned before you arrive and after you leave. Ask what’s included if you’re staying a week.
- Taxes: short-term rentals in Osceola County pay the same lodging taxes as hotels, which were 13.5% in total at last check.
If you only need two or three bedrooms and want daily housekeeping, a hotel suite may be simpler. Our guides to 2- and 3-bedroom suites near Disney World and Orlando hotels with kitchens compare those options.
Where the pool-home communities are
Most of Orlando’s pool-home resorts sit south and southwest of Disney, in Osceola County:
- US-192 west and Old Lake Wilson Road: Windsor Hills, Margaritaville, Windsor at Westside and Solara, close to shops and Disney’s southern entrances. For hotels here, see our best hotels in Kissimmee.
- Reunion (I-4, south of Disney): Encore and Reunion Resort, quieter and golf-focused.
- Kissimmee, east of I-4: Storey Lake, the better pick when Universal and SeaWorld matter as much as Disney.
- Davenport and ChampionsGate: more communities farther southwest, with longer drives. Our Davenport hotel guide covers that area.
Still deciding on an area? Start with our guide to where to stay in Orlando.
How to choose
- You want zero surprises: book Encore or the Margaritaville Cottages, with one operator and a front desk.
- Disney is the main event: Windsor Hills has the shortest drive, and Margaritaville’s resort-fee shuttle covers the parks if not everyone wants to drive.
- You’re doing Disney and Universal: Storey Lake saves time on the Universal days.
- You have 10 or more people: Encore, Reunion and Windsor at Westside offer homes with 9 to 15 bedrooms.
- You’re traveling in winter: budget for pool heat, or pick a cottage where it’s included.
- Several cars: check the HOA vehicle limit before your group drives down. Disney’s standard theme park parking is $35 a day, so a resort shuttle can pay for itself. Our list of Orlando hotels with free parking helps if a hotel ends up being cheaper.
Resort homes with big amenities: see our Evermore Orlando Resort review, the Encore Resort at Reunion review and Orlando resorts for large groups.
Hotel or house? see Orlando hotel vs vacation home: park perks, fees, taxes and space compared.
Frequently asked questions
Do all Orlando vacation homes have a private pool?
No. Encore Resort at Reunion says every home has one, and Windsor Hills says all single-family homes have a screened pool with a spa (townhomes there have plunge pools). At Margaritaville, only the Elite cottages and a few other cottage types listed with a pool have one. At Storey Lake, Solara and other communities, it depends on the individual home, so filter listings for “private pool” and check the photos.
How much does it cost to heat a private pool in an Orlando vacation home?
It depends on the operator. Encore charges $40 a night from May to October and $60 a night from November to April. Reunion charges a daily fee for most homes and warns heating can take up to 12 hours. Margaritaville’s cottages include heating. For homes rented through owners or managers, ask for the nightly price and when to request it.
Which vacation home resort is closest to Disney World?
Of the communities in this guide, Windsor Hills Resort on Old Lake Wilson Road has the shortest drive. Our routing gives about 9 miles and 15 minutes to the Magic Kingdom parking lot. Margaritaville is about 17 minutes away, and Encore about 20 minutes. Allow extra time on US-192 and I-4 at rush hour and on busy park mornings.
Do vacation homes near Disney have shuttles to the parks?
Some do. Encore and Margaritaville include theme park shuttles in the resort fee, with reservations through the concierge. Reunion includes a Disney shuttle that drops off at EPCOT or Hollywood Studios. Windsor Hills’ rental site mentions a paid shuttle but now steers guests to rideshares. At most other communities, you’ll drive, so budget for Disney’s $35 standard daily parking.
Can you use the clubhouse and water park when you rent a vacation home?
Usually, yes, as long as you prove you’re a registered guest. Windsor Hills issues free wristbands, Storey Lake asks for a QR code or booking email, and Windsor at Westside asks for a daily pool waiver. Reunion’s water park access depends on how you booked, so confirm it’s included before you pay.
Bottom line
For most families, the easiest Orlando vacation homes with private pool are at Encore Resort at Reunion and the Margaritaville Cottages, where one operator publishes the rules and the pool is part of the deal. If you’d rather be closer to Disney, choose Windsor Hills. If you’d rather split time with Universal, choose Storey Lake. Whichever you pick, compare the total price including fees, pool heat and the deposit before you book.
Check your dates at Encore Resort at Reunion
Sources checked in October 2026: Encore Resort at Reunion FAQ, Windsor Hills guest FAQ, Margaritaville Cottages Orlando FAQ, Reunion Resort FAQ, Windsor at Westside guest information.