Vacation rentals near Old Town

We found 30,133 vacation rentals — enter your dates for availability

Choose the perfect private vacation rental that's near Old Town. Vacation rentals provide the amenities you need and want for your stay with friends, family, or just your pet, such as parking and a hot tub. You'll be able to choose a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Old Town

Showing deals for:Jul 24 - Jul 31

Image gallery for Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney

Exterior
8.4 out of 10, Very Good, (24 reviews)
Very Good
(24 reviews)

Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney

Kissimmee

8% off
Price is $254
$1,781 for 7 nights
All fees included
Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney

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Find out more about Old Town

Why visit Old Town

  • Family-Friendly Attractions: Enjoy a variety of theme parks and amusement options suitable for visitors of all ages.
  • Historic Town Center: Explore the charming historic center with its delightful shops and local hospitality.
  • Outdoor Recreation: Take advantage of beautiful weather with outdoor activities like golfing and scenic strolls.
  • Vacation Rentals: Choose from a range of comfortable accommodations, including private homes and condos.
  • Vibrant Community: Experience the warm atmosphere and friendliness of the local community during your visit.

Popular types of accommodation around Old Town

If you're planning a getaway to Old Town, you'll find a variety of fantastic vacation rental options to suit your needs. Our most popular accommodations include houses, villas, and condos, all designed for a convenient and comfortable stay. Enjoy essential amenities and the charm of Old Town with our selection of house rentals and vacation rentals that promise transparency, savings, and reassurance for every traveler.

  • Houses: This is the top choice for visitors to Old Town, offering spacious and comfortable settings ideal for families or groups.
  • Villas: These upscale accommodations are the second most sought-after, featuring luxurious amenities and private spaces.
  • Condos: A popular option for those seeking a blend of convenience and comfort, perfect for small families or couples.
  • Apartments: These cozy spaces are great for travelers who prefer a home-like atmosphere during their stay.
  • Cottages: Charming and quaint, these are ideal for a romantic getaway or a peaceful retreat.**

Top attractions near Old Town

Old Town, Kissimmee, Florida, offers an exciting array of attractions for travelers seeking family fun and outdoor experiences. Visitors can enjoy popular destinations such as theme parks, golf courses, and amusement parks, ensuring a memorable vacation filled with entertainment for all ages. Whether you're traveling with family or friends, Old Town is a fantastic place to explore and create lasting memories.

  • Walt Disney World® Resort: Experience the magic at this iconic theme park featuring thrilling rides, enchanting attractions, and beloved characters. Perfect for families, it offers a variety of entertainment options that create unforgettable memories.
  • Orange County Convention Center: Immerse yourself in the local culture at this vibrant arts center, hosting a range of events, exhibitions, and conventions. It's a great place to discover the artistic side of Orlando.
  • Fun Spot America: Just a short walk from Old Town, this amusement park offers exciting rides, go-kart tracks, and fun outdoor activities, making it perfect for adventure-seeking families looking to enjoy a day of excitement.

Things to do recommended for couples

For a romantic getaway in Old Town, Kissimmee, enjoy a fun round at Disney's Fantasia Gardens Miniature Golf, savor a delightful meal at Pirate's Dinner Adventure, and indulge in exquisite wines at True Blue Winery. Each experience offers a unique blend of romance and adventure.

Things to do recommended for families

Families visiting Old Town will love the ESPN Wide World of Sports Complex for its sports vibes, Disney's Typhoon Lagoon Water Park for thrilling water fun, and Wonderworks for exciting arcade adventures. Each location offers a unique experience just a short drive away.

Things to do recommended for groups

Explore the vibrant Disney Springs™ for shopping and dining just 3 miles from Old Town, or enjoy a day of retail therapy at the Orlando Vineland Premium Outlets, located 4 miles away. For some outdoor fun, hit the Mystic Dunes Golf Club, only 5 miles from Old Town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Old Town

If you're traveling with a group, family, pets, or planning for an extended stay, be sure to set your filters according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Old Town with a group: Think about how many bedrooms you’ll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Old Town with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, as well as seek out suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Town: For many, a family vacation wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Old Town: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Old Town

Old Town, Kissimmee, Florida, offers a delightful blend of family-friendly attractions and charming neighborhoods. Explore the historic town center, where fun and recreation await around every corner. Enjoy great views and the warm hospitality of friendly locals while indulging in various excursions. Whether you're seeking thrilling rides or relaxing strolls, Old Town promises a memorable vacation experience for visitors of all ages.

  • Orlando: Orlando is a bustling metropolis known for its family-friendly attractions and entertainment-themed experiences. Located right next to Old Town, it offers a plethora of options for visitors. Enjoy world-famous theme parks, including Walt Disney World and Universal Studios, where adventure and magic await. Orlando is also home to vibrant shopping areas, arts centers, and a variety of resorts. Outdoor enthusiasts can explore beautiful parks and lakes, providing a perfect backdrop for picnics and recreational activities. Don't miss the cultural experiences at local museums and theaters that highlight the city's rich artistic scene.
  • Kissimmee: Kissimmee, where Old Town is situated, is a charming city that attracts families and business travelers alike. Known for its entertainment-themed venues, Kissimmee offers a wide array of shopping areas and resorts. Visitors can indulge in exciting attractions like nearby theme parks and film studios, ensuring fun for all ages. The city's proximity to beautiful beaches also makes it a great destination for those seeking sun and sand. With its friendly atmosphere and variety of activities, Kissimmee is perfect for a memorable vacation filled with adventure and relaxation.
  • Lake Buena Vista: Located a mere 5 miles from Old Town, Lake Buena Vista is a vibrant city that caters to families and business travelers. The area boasts numerous resorts and shopping centers, making it a convenient stop for visitors. Lake Buena Vista is renowned for its close proximity to major theme parks, providing an exhilarating experience for thrill-seekers. Additionally, sports fans can enjoy local stadium events, enhancing the city's entertainment appeal. With its blend of fun and convenience, Lake Buena Vista is an ideal destination for making lasting memories during your vacation.

Best time to go to Old Town

If you're planning a trip to Old Town, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March and June to July, while off-peak times, like January and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnySlightly LowAverage
February64.4°F (18.0°C)Light RainMostly SunnyAverageSlightly Low
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
April72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnySlightly HighSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnySlightly HighSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
September80.4°F (26.9°C)Moderate RainMostly SunnyAverageSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowSlightly Low
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner definitely has its perks. When you join our travel rewards program, OneKey, you'll gain access to exclusive discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy-to-use platform where you can create new travel plans, continue from where you last stopped, or organize your existing itineraries. You'll find your saved or booked properties neatly sorted into sections for Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, just head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near Old Town?
The best vacation rentals near Old Town in Kissimmee, Florida, are typically found within the surrounding neighborhoods. You will find a wide variety of properties, from private vacation homes offering ample space to comfortable condos. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties that still offer easy access to Old Town.

Many top-rated rentals feature amenities such as private pools, shared pools, and outdoor decks or patios. These homes are ideal for families or groups looking for a relaxing stay with convenient features.
Are there any cheap vacation rentals near Old Town?
There are several affordable vacation rentals near Old Town, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around $130 per night. You might find great deals in September and January during the off-season. These rentals often include free amenities such as WiFi, toiletries, and self-parking, so you can have a comfortable stay.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. Many properties are private vacation homes or condos, offering cozy and efficient options for guests looking for great value near Old Town.
What are the best pet-friendly vacation rentals near Old Town?
There are hundreds of pet-friendly vacation rentals near Old Town, making it simple to find a great stay for you and your companion. Over 500 properties, primarily private vacation homes and apartments, are available in Kissimmee, offering amenities such as full kitchens, Wi-Fi, and often private outdoor spaces suitable for pets. Many of these homes explicitly state 'Pets:Permitted' or 'DogsAndCats' policies, with some even offering 'PetsStayfree' options.

When searching for the best pet-friendly vacation rentals near Old Town, it is always wise to review individual property rules regarding pet size, breed, or any additional fees. Old Town itself is generally welcoming to pets in its outdoor settings, allowing guests to stroll with their companions along the pathways.
What are the top vacation rentals with pools near Old Town?
There are over 3,895 vacation rentals near Old Town that feature swimming pools. Guests can choose from private vacation homes with their own outdoor or heated pools, or condos offering access to shared community pools, some with waterslides or poolside bars. These properties are concentrated in areas surrounding Old Town, providing options like private backyard pools or communal pool complexes. Many homes come equipped with full kitchens, multiple bedrooms, Wi-Fi, and amenities like pool sun loungers, making them ideal for families and groups seeking comfort and entertainment.

When selecting your rental, consider whether a private pool for seclusion or a shared pool with additional features like a hot tub or children's pool best suits your needs. For stays during cooler months, look for heated or indoor pool options to ensure year-round enjoyment. Checking availability for peak summer dates in advance is advisable to secure your preferred property.
What are the best family vacation rentals near Old Town?
There are over 3200 family-friendly vacation homes near Old Town, offering ample space and comfort for groups. These rentals often feature full kitchens, washer/dryers, and outdoor play areas like yards or patios. Many also include amenities such as game rooms, video games, and even access to children's pools or water parks, ensuring entertainment for all ages.

When selecting a property, look for homes that provide separate spaces for adults and children to relax, and practical amenities like laundry facilities to make your stay smoother. Staying close to Old Town means less travel time and more opportunities to enjoy the area's attractions.
Are there any luxury vacation rentals near Old Town?
Near Old Town, guests can find several luxury vacation rentals that combine the local scenery with modern comfort. These properties often feature private pools, hot tubs, air conditioning, and premium bedding. Many homes also boast amenities like deep soaking bathtubs, private chefs, and lake views, ensuring a sophisticated stay.

These homes are ideal for families or larger groups, often including conveniences such as high-speed WiFi and entertainment options. Many of these top-tier stays are managed by highly rated Vrbo hosts, offering a professional and premium experience.
How much is a vacation rental near Old Town?
Vacation rentals near Old Town offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around $130 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around $240 per night, offering more comfort and privacy. For those seeking a more luxurious experience, upscale options can cost $345 or more per night, often featuring additional space and amenities.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
Where should I stay when visiting Old Town?
When visiting Old Town, several areas offer excellent vacation rental opportunities. The immediate vicinity of Old Town is great for guests who want to be steps away from the classic car shows, unique shops, and family entertainment.

For those seeking a blend of convenience and proximity to other major attractions, properties along West Irlo Bronson Memorial Highway (US-192) provide easy access to Old Town and offer a wide selection of homes. These rentals are a short drive from the main entrance, allowing for quick visits.

Another appealing option is the area around Celebration, which presents a charming, master-planned community feel. Properties here are a comfortable drive from Old Town, offering a different ambiance while remaining well-connected to the area's entertainment options.
What is the cheapest month to stay near Old Town?
The cheapest time to find vacation rentals near Old Town is typically during the late Summer to early Autumn (September) and Winter (January), excluding any major holiday weeks. September and January are frequently the cheapest months, often providing the best deals on vacation rentals. Guests can often find lower rates during these months, along with greater availability.
Are there any lakefront vacation rentals near Old Town
Lakefront vacation rentals are available near Old Town, primarily situated on the shores of Lake Tohopekaliga and other surrounding lakes. These properties are a short drive from Old Town, offering convenient access to water activities such as kayaking, fishing, paddleboating, or simply relaxing by the shore.

These vacation rentals often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy water views and unwind in peaceful surroundings.
Are there any monthly vacation rentals near Old Town?
Vrbo offers excellent options for monthly vacation rentals near Old Town, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Old Town.
Are there any last-minute vacation rentals near Old Town?
Vrbo makes it simple to find last-minute vacation rentals near Old Town that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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