Vacation rentals in Osceola County

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Top cities to explore in Osceola County

Driving out of the park I saw this lovely male peacock strutting his stuff for a little attention.

St. Cloud

Vacation Rentals
St. Cloud
Located south of Kissimmee FL, the area is being brought back to its natural state, there is a couple of walking trails and scientific studies are also done here.

Poinciana

Vacation Rentals
Poinciana

Top vacation rentals in Osceola County

Vacation Village at Parkway

Vacation Village at Parkway

3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
8.13 mi from city center
$98 nightly
The price is $112 total per night
$112 total
Aug 25 - Aug 26
Total includes taxes and fees
7 outdoor pools, 7 hot tubs, and a gym are all featured at this smoke-free condo. Bring the family and enjoy the children's pool, playground, and arcade/game room. WiFi in public areas is free.
Pool
Hot Tub
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
12.75 mi from city center
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This smoke-free aparthotel features free water park access, a full-service spa, and a restaurant. Bring the family and enjoy the lazy river, waterslide, and arcade/game room. Enjoy the outdoor pool and perks like free self parking and free WiFi.
Pool
Hot Tub
Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando

2.5 out of 5
2754 Florida Plaza Blvd, Kissimmee, FL
Free Cancellation
7.15 mi from city center
$114 nightly
The price is $130 total per night
$130 total
Sep 14 - Sep 15
Total includes taxes and fees
This aparthotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
7593 Gathering Drive, Kissimmee, FL
11.08 mi from city center
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This luxury aparthotel features a golf course, free water park access, and 7 restaurants. Bring the family and enjoy the lazy river, mini golf, and kid-friendly dining. Relax with a drink at one of the 2 poolside bars and enjoy the 11 outdoor pools and gym.
Pool
Hot Tub
Club Wyndham Cypress Palms

Club Wyndham Cypress Palms

3.5 out of 5
6.02 mi from city center
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2 outdoor pools, 2 hot tubs, and a 24-hour gym are all featured at this smoke-free aparthotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, a picnic area, and luggage storage are also on offer.
Pool
Hot Tub
Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ

4 out of 5
5780 Golden Hawk Way, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
7.04 mi from city center
$281 nightly
The price is $319 total per night
$319 total
Aug 17 - Aug 18
Total includes taxes and fees
Free water park access, 2 restaurants, and 2 outdoor pools are all featured at this Mediterranean condo resort. Bring the family and enjoy the waterslide, arcade/game room, and kid-friendly dining. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Pool
Hot Tub
Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ

3 out of 5
3070-B Secret Lake Drive, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
13.77 mi from city center
$269 nightly
The price is $306 total per night
$306 total
Aug 18 - Aug 19
Total includes taxes and fees
2 outdoor pools, 2 hot tubs, and a 24-hour gym are all featured at this smoke-free aparthotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Enjoy a meal from the a restaurant and perks like free self parking.
Enchanted Dreams

Enchanted Dreams

2.5 out of 5
2624 Calistoga Ave, Kissimmee, FL
3.07 mi from city center
$116 nightly
The price is $132 total per night
$132 total
Aug 22 - Aug 23
Total includes taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Pool
Kitchen
The Irlo

The Irlo

4 out of 5
5565 W Irlo Bronson Memorial Hwy, 356, Kissimmee, FL
6.72 mi from city center
$151 nightly
The price is $172 total per night
$172 total
Aug 17 - Aug 18
Total includes taxes and fees
This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Kitchen
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
3151 Pantanal Lane, Kissimmee, FL
11.88 mi from city center
Get rates
This aparthotel features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Grand Lake Resort

Grand Lake Resort

3 out of 5
7770 W Irlo Bronson Memorial Hwy, Kissimmee, FL
11.87 mi from city center
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This aparthotel features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Guests will appreciate free perks like free self parking and WiFi in public areas.
Pool
Kitchen
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38

Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38

3.59 mi from city center
Get rates
A water park and an outdoor pool are featured at this smoke-free villa. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A gym, a hot tub, and laundry facilities are also on offer.
Pool
Hot Tub
Lifetime of Vacations Resort

Lifetime of Vacations Resort

3 out of 5
7770 W Irlo Bronson Memorial Hwy, Kissimmee, FL
11.93 mi from city center
Get rates
This condo features an outdoor pool and a gym. A business center, a garden, and a picnic area are also on offer.
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4 out of 5
Formosa Vly Pl, Kissimmee, FL
12.21 mi from city center
$434 nightly
The price is $482 total per night
$482 total
Aug 17 - Aug 18
Total includes taxes and fees
An outdoor pool is featured at this vacation home, along with concierge services. Take advantage of the free self parking.
Barefoot Suites

Barefoot Suites

3 out of 5
2750 Florida Plaza Blvd, Kissimmee, FL
7.14 mi from city center
$101 nightly
The price is $114 total per night
$114 total
Aug 17 - Aug 18
Total includes taxes and fees
This aparthotel features an outdoor pool and a hot tub. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Guests will appreciate free perks like free self parking and WiFi in public areas.
Pool
Hot Tub
Lakeview Luxury Villa with Everything

Lakeview Luxury Villa with Everything

5.02 mi from city center
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A water park and a gym are featured at this smoke-free villa. Families will appreciate the arcade/game room and onsite laundry facilities.
Pool
Kitchen
Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4 out of 5
2621 Sunrise Shores Drive, Kissimmee, FL
11.35 mi from city center
Get rates
This vacation home features an outdoor pool and a gym. Bring the family and enjoy the free kid's club, playground, and arcade/game room. Enjoy the hot tub and perks like free self parking and free WiFi.
Pool
Hot Tub
Royal Laguna Villas By Magical Memories

Royal Laguna Villas By Magical Memories

3.5 out of 5
5000 Laguna Bay Circle, Kissimmee, FL
4.82 mi from city center
Get rates
This vacation home features an outdoor pool and a gym. Enjoy the outdoor tennis court and perks like free WiFi. Laundry facilities are provided for your convenience.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Best Way to Find Vacation Rentals in Osceola County 

How cheap is a vacation rental in Osceola County?


You can find Osceola County vacation rentals from just $112 per night. 


How do you look for the best vacation rental deals in Osceola County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Osceola County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Osceola County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Osceola County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Osceola County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Osceola County?


Whether you’re a winter wanderer or planning a summer sojourn, Osceola County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Osceola County?


Take your pick from the excitement of the big Osceola County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Osceola County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Osceola County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.