Home rentals with a pool near Old Town

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Top-rated rentals with a pool near Old Town

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A resort-style swimming pool is framed by palm trees and lounge chairs. The image shows a screened patio with a private jacuzzi and outdoor dining space, along with a colorful water slide visible nearby. The themed bedroom features bright decor and ample bedding, appealing to families.
Townhouse in Kissimmee
4.92 out of 5 average rating, 109 reviews

#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

Top Guest favourite
An aerial view of the resort reveals a scenic layout surrounding a sparkling blue pool and vibrant water slides. Palm trees line the poolside area, where lounge chairs are arranged around the water's edge. The lush greenery and nearby lake add a natural touch to the inviting ambiance.
Townhouse in Kissimmee
4.97 out of 5 average rating, 259 reviews

*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!

Top Guest favourite
A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.
Home in Kissimmee
4.92 out of 5 average rating, 104 reviews

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 ☕️

Top Guest favourite
A private hot tub is situated on a patio surrounded by a screen enclosure, offering views of a tranquil lake. A fountain can be seen in the distance, enhancing the serene atmosphere. Steps lead up to the hot tub, providing easy access.
Townhouse in Kissimmee
4.95 out of 5 average rating, 226 reviews

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.

Guest favourite
A resort pool area is surrounded by palm trees and sunshine, featuring lounge chairs under white umbrellas. A paved deck encircles the pool, creating a relaxing atmosphere for guests. A blue slide can be seen in the background, enhancing the recreational space.
Townhouse in Kissimmee
4.87 out of 5 average rating, 127 reviews

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.

Top Guest favourite
A large swimming pool is surrounded by lush palm trees and lounge chairs, providing a relaxing atmosphere. The vibrant blue water reflects the bright sky, while a resort building stands in the background, featuring expansive windows and outdoor seating areas under shaded umbrellas.
Townhouse in Kissimmee
4.92 out of 5 average rating, 118 reviews

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!

Guest favourite
A resort area is depicted with a large swimming pool surrounded by palm trees. The two-story building features numerous windows and outdoor seating, creating an inviting space. Soft evening light reflects on the water's surface, enhancing the tranquil atmosphere.
Home in Kissimmee
4.87 out of 5 average rating, 123 reviews

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

Guest favourite
The image showcases a spacious townhouse complex within a gated resort, featuring warm-toned exterior walls and a distinctive red-tiled roof. Surrounding greenery includes palm trees and well-maintained landscaping. Ample parking spaces are visible in front, highlighting the convenience of access.
Townhouse in Kissimmee
4.84 out of 5 average rating, 335 reviews

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

Guest favourite
The image presents a four-part collage, featuring a bright bedroom with two spacious beds adorned with decorative pillows, a private hot tub surrounded by nature, a resort pool with loungers and a water slide, and a clubhouse area with expansive outdoor seating and vibrant landscaping.
Townhouse in Kissimmee
4.85 out of 5 average rating, 133 reviews

♥︎ 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!

Superhost
Townhouse in Kissimmee
4.85 out of 5 average rating, 300 reviews

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!

Top Guest favourite
A private screened hot tub is featured in the foreground, surrounded by an inviting outdoor seating area with a table and chairs. Lush tropical plants enhance the atmosphere, while a large mirror reflects the vibrant orange wall and soft natural light from the spacious windows.
Townhouse in Kissimmee
4.95 out of 5 average rating, 220 reviews

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.

Top Guest favourite
A yellow cottage is featured, with a welcoming entrance that includes a set of wooden steps leading to a covered porch. White railings frame the porch, while a ceiling fan hangs above. Lush greenery and flowering plants are positioned near the entrance, enhancing the overall charm.
Cottage in Kissimmee
4.95 out of 5 average rating, 503 reviews

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

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

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee
  6. Old Town
  7. Rentals with pools