Stunning Villa w/ Private Pool Near DisneyN°001
West Lucaya, USA
Kissimmee
Private poolHot tubAir conditioning
From $448 per night
Smiling House brings together 3 hand-selected luxury houses in Orlando — each one chosen for its setting, its design and the service around it. Orlando is Central Florida's theme park capital, home to Walt Disney World, Universal and SeaWorld. From intimate hideaways for two to expansive homes for family and friends, every house is booked directly with our team — no middle-man, no surprises. Browse the homes below, then speak to a concierge who knows Orlando first-hand about dates, rates and the details that make a stay effortless.
Updated October 2026
Free Grill for AprilN°002
Orlando, USA
Davenport
Hot tubGymAir conditioning
From $213 per night
Storey Lake Luxury, 6BR Pool Home Near ParksN°003
Orlando, USA
Kissimmee
Private poolGymAir conditioning
From $298 per night
All 96 villas in Orlando
Every home in Orlando that can be booked with Smiling House, as a plain list.
- Themed 5 Bedrooms at Storey Lake
- 13 Beds | Movie Theater, Game Room, Water Park
- 3-story villa w/ pool, game room & theater
- 3BR Family Apartment for 8 Peaceful Residential Retreat
- 5BR Themed Family Villa Near Disney with Private Pool
- 6BR Near Disney, Pool, Games and Themed Rooms
- 8BR | Pool + Spa | 20 Min to Disney
- 9BR Family Retreat, Private Pool, Storey Lake
- Amazing beach house near the parks!
- Ocean View Beach House in Orlando
- Charming Home, Ideal Location, Spacious, Game Room
- Chic 10BR Retreat with Themed Rooms & Pool
- Chic 6BR, Pool, Themed Rooms, Near Disney
- Chic 8BR All Suites with Pool and Game Room
- Chic Modern Escape, 12BR, Pool and Game Room
- Classy 6BR Home with Private Pool
- Comfortable 3BR townhouse w/ pvt patio
- Comfortable 6BR home w/ private pool
- Cozy Family 3BR Townhouse Perfect Stay for 6 Guests!
- Davenport Luxury Villa by AllevoHomes
- Disney Bliss Themed Rooms, Game Room, Private Pool
- Disney Delight With Modern Comforts
- Lake View Seven Bedroom Villa in Orlando
- Spacious Manor Near Disney in Florida
- Epic 10BR Solara Retreat, Themed Fun & Pool
- Luxury Villa with Private Theater in West Lucaya
- Epic Luxury Villa near Disney, Game Rooms & Pool
- Family Friendly 5BR Home Pool, Patio & Room for 10!
- Family Fun Oasis, 6BR, Game Room, Pool
- Family Luxury 9BR Villa Poolside Bliss n Pool Table Fun
- Family home w/ private pool near Disney
- Family villa w/ pool, hot tub & game room
- Family-friendly retreat near Disney w/ pool
- Beachfront Penthouse in Miami Beach
- Beachfront Ocean View Penthouse in Miami Beach
- Skyline View Penthouse in Miami Beach
- Free Grill for April
- Beachside Four Bedroom Villa in Orlando
- Group-friendly retreat w/ pool & free water park
- Heated Pool + Waterpark+ Game Room + Lazy River
- Home 9 Bed Themed Rooms, Pool, Storey Lake
- Family-Friendly Retreat with Game Room in Orlando — Four Corners
- Kissimmee townhouse w/ shared pool & BBQ
- Luxurious 8 Bedroom 5 Bath, Resort, Arcade and Theatre
- Luxurious Transitional Villa with Water Views
- Luxury 15BR Suites, Pool and Themed Bedrooms
- Luxury 7BR Villa, Pool, Spa & Game Room
- Luxury 8BR Theater Game Pool Golf Firepit - Disney
- Luxury 8BR Themed Villa with Private Pool
- Luxury 9 Bedroom w/ Arcade, Theatre, Pool! 2 Free Waterparks!
- Luxury 9BR Retreat, Pool, Themed Rooms, New Floor
- Luxury 9BR Solara Home, Themed Fun & Pool
- Balcony Three Bedroom Home in Orlando
- Luxury Decor 6BR at Storey Lake sleeps 16
- Luxury Incredible Themed Home, best vacation
- Luxury Paradise in Orlando Best Location
- Luxury Themed 8BR with Pool, Game Room, Theater
- Luxury Villa near Disney: Arcade, Theater, & more!
- New 3BR, Luxury Design with Lake View
- Resort-Style Villa with Private Pool in Orlando
- Newly Furnished Villa with Covered Outdoor Dining and Water Views
- Orlando Most Incredible Themed 10BR Villa
- Perfect View Villa with Amazing Pool
- PgaVillageResort by AmericanVacationLiving 2 BR
- PgaVillageResort by AmericanVacationLiving 7 Room
- Prestigious Home with Beautiful Outdoor Covered Deck
- Private theater | Pool and spa | Sleeps 18
- Resort home w/ pool, hot tub & game room
- Retreat Near Orlando Park & Golf Course
- Saltwater Pool & Spa Retreat Near Honeymoon Island
- Spacious Seven Bedroom Villa in Orlando
- Spacious Retreat with Game Room in Orlando
- Sophisticated 6BR at Storey Lake
- Spacious 5BR Home with Pool near Disney
- Spacious 5BR, Private Pool, Beautiful Decor
- Spacious Family Escape, Pool & Game Room
- Spacious home w/ pool & resort access
- Spectacular Villa with Most Amazing Views of Downtown Miami
- Steps to Beach, Shared Heated Pool, 4 Decks, Game Room
- Storey Lake Luxury, 6BR Pool Home Near Parks
- Stunning 10 Bed Home with Themed Rooms, Pool
- Event-Ready Townhouse in Orlando
- Stunning 6BR, Private Pool, Prime Location
- Stunning 7BR Home with Themed Bedrooms
- Stunning Miami Villa with Water Views
- Stunning Villa w/ Private Pool Near Disney
- The Power-Up Palace, 9 beds, private pool
- Themed 7Bedroom and Pool 18 guests
- Cozy Five Bedroom Villa in Orlando
- Tropical Modern Villa with a Refreshing Infinity Pool
- Ultimate 10 Bed Luxury Retreat with Epic Playroom
- Unique Luxury Villa, Pool, Games and Themed Beds
- Upscale 9BR Stay with Pool and Themed Rooms
- Villa near Disney w/ heated pool
- Waterfront Pink House with Private Dock & Pool!
- Windsor Resort, Private Pool & Theater, Game Room
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.
Houses in other destinations
Frequently asked
How do I book a house in Orlando?
Choose a home below and send an enquiry, or ask to book directly. A Smiling House concierge confirms availability and rates with the owner and handles the booking end to end — you deal with our team, not a faceless platform.
What's included when I rent a house in Orlando?
Every home is fully furnished and privately yours for the stay. Concierge support, and often housekeeping and local recommendations, come as standard; specific services vary by property and are listed on each home's page.
Is it cheaper to book direct with Smiling House?
Booking direct removes the platform mark-ups that sit on OTA listings, and puts you in touch with a team that knows Orlando personally. You get the real home, the real price and a human who answers.
How many houses are available in Orlando?
3 houses are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.