
Home rentals with a pool near Old Town
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Old Town
Guests agree: these stays are highly rated for location, cleanliness and more.

#2609 Resort Home near Disney Themed Jacuzzi Pool
Relax in this LARGE FULLY RENOVATED LUXURY DESIGNER HOME in the famous REGAL OAKS RESORT w/ THEMED BR near DISNEY WORLD in ORLANDO FLORIDA! Enjoy the STUNNING LAKE FRONT VIEW, PRIVATE JACUZZI, NEW STYLISH FURNITURE, HEATED POOL, Waterslides, Poolside Bar, GAME ROOM, BILLIARD TABLES, Ping Pong, Restaurant, GYM, Tennis Court, and 24/7 Security Guard! - Walk 5 min to Old Town Amusement Park and World Food Trucks. - Drive 8 min to DISNEY, 20 min UNIVERSAL STUDIO, 15 min SEAWORLD and DISNEY SPRINGS

*LAKEVIEW* Resort 4m Disney! Private Spa Wi-Fi
Welcome to our personal Old Town Oasis! Beautiful LAKEVIEW property in Regal Oaks Resort! Coffee, Nespresso, tea, free Wi-Fi! It's close to the theme parks and everything that Orlando has to offer! Come relax in your own private spa after a long day at the parks, or enjoy the resort water slides, heated pool, pool side games and tiki bar with food and beverage, arcade games in the Clubhouse and more. If you're up for more fun, walk to Old Town next door! Our place is BABY and KID FRIENDLY!

3BR / 2BR Heated Pool Home 7 Min to Disney |
✨ Experience comfort, style, and a private heated pool 💦 (optional) just 7 minutes from Disney World! This 3BR/2BA Kissimmee home is perfectly located near theme parks, shopping, and dining — and designed for families looking to unwind in a sparkling-clean, beautifully curated space. 📍Prime Kissimmee Location ⭐7 Min– Walt Disney World ⭐5 min–Orlando Premium Outlets ⭐15 min – Universal Studios, SeaWorld, Epic Universe 🎢 ⭐ 25 min – MCO Airport ✈️ ⭐ Walk to Walmart, Publix & Starbucks ☕️

4.95 Rated Pool Home 10 Min to Disney
Trusted by over 400 guests with a 4.95 rating. Quiet pool home designed for easy, stress free stays. Spotless, clutter free, and exactly as described. Fast WiFi and simple self check in. 10 minutes to Disney and major attractions. “Spotless, easy check in, and perfect location.” “Exactly as described. Would stay again.” 2-bedroom townhouse in the gated Regal Oaks Resort Private hot tub overlooking a peaceful lake, ll Resort-style amenities like pools, water slides, a fitness center.

Entire townhouse, Resort style, 5 miles to Disney!
Feel right at home in our outstanding location JUST 5 MILES FROM DISNEY! Exceptional 2 bed/2.5 bath townhome features premium one King bed, 2 twin beds and a queen size sofa bed with fully equipped kitchen, washing machine, smart TVs, a private patio, Jacuzzi and lake view. Contemporary furnishings, luxury feel. Located in gated resort with clubhouse, beautiful pool, water slide, gym, tennis court and more. Within 10 minutes drive to a variety of restaurants, shops, Fun Spot and more.

Spacious Lakefront Townhome – 4mi to Disney!
Your perfect Kissimmee getaway starts here! This updated 4BR/3BA lakefront townhome in gated Regal Oaks Resort is just 4 miles from Disney. Relax with peaceful lake views from your private patio, cook in the full kitchen, and unwind in the spacious open living area. Enjoy resort amenities like a pool with water slides, hot tub, gym, tennis courts, and on-site dining. Ideal for families or friends, this home blends comfort, fun, and unbeatable convenience for your Orlando adventure!

Resort TH 2b/2.5b With Private Hot Tub near Disney
Visit Regal Oaks Resort, with an onsite waterpark and private hot tub. We're close to everything in Orlando and a 10 min drive to Disney! Our Resort-Style Villa Includes: ❤Onsite Waterpark and Heated Pools ❤Walkable to Old Town Restaurants and Shops ✔No Hidden Fees ✔Onsite Fitness Center ❤24/7 Security ✔Onsite Concierge, Restaurant and Bars Our Home Offers: ❤Private Hot Tub ✔Comfy King and 2 Full-Size Beds ❤Fast WiFi ✔Cable TVs ✔Private Patio ✔Washer/Dryer ✔Stocked Kitchen

Comfy 3 bdrs w/private jacuzzi 5 min *Disney*
This spacious and recently upgraded decor townhouse is located in the beautiful Regal Oaks Resort. Regal Oaks is a private, gated Vacation Home Community and Resort. Located just a few minutes away from the traditional Old Town parks,shops and dinning and only 20 minutes away from Disney,this house will bring much fun to families, friends and groups looking for a weekend of fun or enjoy the great theme parks around. ** NO CARPETS **free parking, wifi and all resort’s amenities

♥︎ Disney-3 miles ♥︎ Private HotTub ♥︎Top Resort♥︎
Our gated-community townhouse offers a resort feeling with all the comforts of home, peaceful & quiet, yet central to Disney, Old Town, and all major attractions. After an exciting family day, relax in your private patio hot tub and enjoy the nature, or soak up some sun poolside at the resort. Fun for adults and kids of all ages! Also enjoy the resort tennis courts, pool table, gym, restaurant, and poolside snack bar! NO RESORT FEES! FREE PARKING!

Free Waterpark- Fantasy World, Mickey and Minnie
Discover magic in our charming villa at Fantasy World Villas, near Disney, Universal & Sea World. Enjoy a whimsical Mickey & Minnie-themed room, king-size master bedroom, modern kitchen, and private patio. Resort: pools, slides, lazy river, kids' activities, gym, sports courts & more. Walk to shops & restaurants. Free WiFi, parking & resort access. Create unforgettable memories in our enchanting villa, just steps from theme parks & resort fun! Book now!

2 BR Harmony House at Regal Oaks Resort
Come get away to our modern, super-clean, self-contained garden oasis town house in the Regal Oaks Resort - close to grocery stores and take out food - minutes walk from Old Town Kissimmee and a short drive from Disney's ESPN - World of Sports and Town Center Celebration. We are 15 minutes drive from Epic - Universal and Disney parks. Our private screened in hot tub is the perfect place to relax in the Florida sun or under our sun shade.

Bright & Cozy Cottage Near Disney
My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.
Popular amenities for rentals with a pool near Old Town
House rentals with a pool

Resort Style 3Br/2.5Ba w/ Private Jacuzzi, and BBQ

Modern 2BR Home w/ Hot Tub, 15min Disney

Pet Friendly Large 1 Bed/1Bbath condo at the Melia

Disney New Neighbor

#2718 Stunning LakeFront Priv Spa Pool Disney Epic

Disney Retreat | BBQ, King Bed, Pool, Game Room +

Entire Modern Home near Disney • Pool & Game Room

New! Resort home with spa 10 min from Disney
Condo rentals with a pool

Enchanting Newly Renovated 1.5miles to Disney (760

Suites at Lake Buena Vista close Disney Spring A2

King Bed Small Studio Disney World Universal

Modern Lake view Condo 1 mile from Disney

Luxurious Spot 10 Mins Away to Most Attractions!!!

Holiday Sunny Central Condo w/ Pool & Balcony

Mickey Mouse Themed Getaway next to Disney 1

Lakefront Resort Condo near Disney and Universal
Other holiday rentals with a pool

It's too much like a elegant mini-hotel (3)

Townhouse - 5 miles to Disney!

Resort Townhome with Water Park Near Disney

Modern Vacation Cottage near Walt Disney World

Disney/Universal Home Away from Home!

Entire Home - Luxury Resort - 3 bedrooms

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Cozy Orlando Area Cottage - 4 Miles to Disney
Quick stats about rentals with a pool near Old Town

Total holiday rentals
Explore 630 holiday rentals in Old Town

Nightly prices starting at
Old Town holiday rentals start at $60 AUD per night before taxes and fees

Verified guest reviews
Over 37,080 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 320 rentals that welcome pets

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wi-Fi availability
630 of Old Town holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Old Town rentals

4.7 Average rating
Old Town stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Family-friendly rentals Old Town
- Apartment rentals Old Town
- Villa rentals Old Town
- Townhouse rentals Old Town
- Rentals with a washing machine and dryer Old Town
- Rentals with outdoor seating Old Town
- Fitness-friendly rentals Old Town
- Condo rentals Old Town
- Pet-friendly rentals Old Town
- Rentals with lake access Old Town
- Resort rentals Old Town
- Rentals with a patio Old Town
- Waterfront rentals Old Town
- Serviced apartment rentals Old Town
- Rentals with an EV charger Old Town
- Rentals with a fireplace Old Town
- House rentals Old Town
- Hotel rooms Old Town
- Rentals with a hot tub Old Town
- Rentals with breakfast Old Town
- Rentals with pools Kissimmee
- Rentals with pools Osceola County
- Rentals with pools Florida
- Rentals with pools United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Walt Disney World Resort Golf
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Epcot
- ESPN Wide World of Sports
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Universal's Islands of Adventure
- Ventura Country Club
- Shingle Creek Golf Club
- Crayola Experience




