TOP 30 Florida vacation rentals with pool in Kissimmee, Florida

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Located in Kissimmee, Florida, Quality Vacation Homes offers a range of beautiful and comfortable lodging options for those looking to enjoy a relaxing and luxurious vacation. Our vacation homes are fully equipped with all the amenities needed for a comfortable stay, including spacious living areas, fully equipped kitchens, and private pools. Whether you're looking for a cozy retreat for a romantic getaway or a spacious home for a family vacation, Quality Vacation Homes has the perfect accommodation for you. Our prime location allows easy access to all the attractions and activities that Kissimmee has to offer, making it the ideal choice for your next vacation. Book your stay with us today and experience the ultimate in quality vacation living.

Caribe Cove Resort in Kissimmee by Vacasa offers luxurious vacation rentals for every getaway. Located at 9000 Treasure Trove Lane in Kissimmee, Florida, this resort is the perfect destination for a relaxing and enjoyable stay. With 53 vacation rentals equipped with internet access, guests can stay connected throughout their trip. The professional housekeeping team at Caribe Cove ensures that each rental is thoroughly cleaned and stocked with amenities, allowing guests to simply settle in and relax. Whether you're looking for a lodging option, real estate agency, or travel agency, Caribe Cove Resort has everything you need for your next getaway. Book your stay at Caribe Cove Condominiums in Kissimmee, FL for a memorable vacation experience.

Reunion Vacation Homes is a lodging, real estate, and travel agency located at 7531 Osceola Polk Line Road in Davenport, Florida, United States. Specializing in bringing friends and family together in Orlando Vacation Home Rentals and Anna Maria Island Rentals, Reunion Vacation Homes offers a wide range of vacation rentals in select Orlando area resorts close to Disney® such as Reunion Resort, The Retreat at Champions Gate, Windsor at Westside, and more. With options ranging from 2-3 bedroom condos to 10-14 bedroom luxury villas, there is something for everyone. Whether you're looking for top villa rentals near Disney World® in Kissimmee & Davenport, or luxury mansions in Reunion Resort, Reunion Vacation Homes has you covered. With over 300 luxury villas and condos to choose from, guests can enjoy amenities such as private pools, golf course views, and proximity to major attractions.

Orlando Short Term Rentals is a premier real estate and travel agency located at 1050 Plaza Drive in Kissimmee, Florida. Specializing in providing top-notch short term rental properties in the Orlando area, our agency offers a wide range of accommodations to suit every traveler's needs. Whether you're visiting for a family vacation, business trip, or special event, our team is dedicated to helping you find the perfect rental property to make your stay unforgettable. With a focus on customer satisfaction and personalized service, Orlando Short Term Rentals is your go-to destination for a seamless and enjoyable rental experience in the Sunshine State.

Rentals in Emerald Island Resort is a reputable real estate and travel agency located at 8515 Crystal Cove Loop in Kissimmee, Florida, United States. Specializing in vacation rentals within the luxurious Emerald Island Resort, this agency offers a wide range of beautiful properties for guests to choose from. With top-notch customer service and a dedication to providing unforgettable experiences, Rentals in Emerald Island Resort is the perfect choice for those looking to explore the magic of central Florida. Whether you're seeking a cozy villa for a romantic getaway or a spacious home for a family vacation, this agency has something for everyone. Book your stay with Rentals in Emerald Island Resort and make your dream vacation a reality.

Windsor Hills Private Rentals is the official rental website for the Windsor Hills Resort in Kissimmee, Florida. Endorsed and run by the Resort Management Committee, we offer a wide selection of vacation rentals in the most popular resort community in the Orlando area. With no commission or booking fees, you can secure your dream vacation rental directly with the property owner or manager. Our advanced search functionality helps you find the perfect accommodation, whether you're looking for a villa, townhome, or condo. The resort is located just 2 miles from Walt Disney World, making it the ideal location for a family vacation, business event, wedding, or honeymoon. Enjoy the amenities of the Windsor Hills Resort, including a clubhouse, lagoon-style pool, water park, fitness center, playground, and more. With easy access to top golf courses and major theme parks, renting in Windsor Hills puts you in the center of the action. Book your perfect vacation rental property now with Windsor Hills Private Rentals.

Holiday Inn Club Vacations at Orange Lake Resort is a luxurious lodging destination located in Kissimmee, Florida, United States. This resort offers spacious accommodations, top-notch amenities, and a wide range of activities for guests of all ages. Whether you're looking to relax by the pool, play a round of golf, or explore the nearby theme parks, this resort has something for everyone. With its convenient location and exceptional service, Holiday Inn Club Vacations at Orange Lake Resort is the perfect choice for your next vacation getaway.

Encantada Resort Vacation Townhomes by IDILIQ is a luxurious lodging option located at 3070 Secret Lake Drive in Kissimmee, Florida. This resort offers spacious and comfortable self-catering townhomes just outside Walt Disney World, making it the perfect choice for vacationers looking for larger spaces and great amenities. Each townhome at Encantada Resort is individually owned and features a fully equipped kitchen, private patio with a hot tub, and all the facilities needed for a perfect vacation in Orlando. The resort is ideal for families and larger groups, with two, three, and four-bedroom options available.

Legacy Vacation Resorts Kissimmee/Orlando - Near Disney is a charming lodging institution located at 2800 North Poinciana Boulevard in Kissimmee, Florida, just a stone's throw away from the magical world of Disney. This resort offers comfortable accommodations and a range of amenities to make your stay unforgettable. Enjoy spacious suites, a sparkling swimming pool, fitness center, and easy access to all the attractions that Orlando has to offer. Whether you're visiting with family or friends, Legacy Vacation Resorts Kissimmee/Orlando is the perfect home base for your Florida vacation.

Escape to Regal Oaks Resort Vacation Townhomes by IDILIQ, located at 5780 Golden Hawk Way in Kissimmee, Florida, United States. This institution offers lodging, real estate, and travel agency services. Nestled in the heart of Orlando, our resort is the perfect retreat for families, couples, and groups of friends looking for a magical getaway. Enjoy spacious accommodations, world-class amenities, and a range of activities for the whole family. Unwind in a fully equipped kitchen, relax on your private screened patio, and indulge in the resort's pool oasis. With multiple bedrooms, these vacation homes cater to diverse needs, ensuring a truly extraordinary escape. Staycation savings are available exclusively for Florida and Georgia residents. The resort offers a Cabana Pool Bar for tropical beverages, a family-friendly sports bar and grill, and easy access to popular theme parks and attractions. Dive into the expansive pool, challenge your skills on the tennis and pickleball courts, and enjoy the arcade and market on-site. Regal Oaks Resort is part of the IDILIQ Group of companies, offering luxurious accommodations in sought-after holiday destinations. Experience the perfect blend of comfort and family-friendly fun at Regal Oaks Resort Vacation Townhomes by IDILIQ.

Bella Vida Vacation Homes is a luxurious lodging option located in Kissimmee, Florida. As a real estate and travel agency, they offer a wide range of vacation homes for rent, providing guests with the ultimate comfort and convenience during their stay. Situated at 1172 Marcello Boulevard, Bella Vida Vacation Homes is the perfect choice for travelers looking for a home away from home experience in the Sunshine State. With top-notch amenities and a prime location near popular attractions, Bella Vida Vacation Homes ensures a memorable and enjoyable stay for all guests.

Vacation Village at Parkway is a luxurious lodging institution located at 2975 Arabian Nights Boulevard in Kissimmee, Florida. After a fun-filled day exploring the nearby theme parks, guests can unwind in the spacious one- and two-bedroom suites offered at the resort. With seven heated pools, seven hot tubs, three nature trails, and 22 barbecue grills, there are plenty of amenities to enjoy on-site. Additionally, guests can take advantage of the two fitness centers, concierge desk, and arcade during their stay. The resort also provides shuttle service to the theme parks for added convenience. Vacation Village at Parkway has been recognized with a Gold Crown Status by RCI since 2001, highlighting its exceptional standards in various areas. The resort has also received Tripadvisor's Travelers' Choice Award for its outstanding guest reviews.

747 Vacation Homes is a premier vacation rental agency located in Kissimmee, Florida. Situated at 8701 West Irlo Bronson Memorial Highway, this institution offers a wide selection of luxurious vacation homes for visitors to enjoy while exploring the attractions of the Orlando area. Whether you're looking for a cozy condo, a spacious villa, or a private pool home, 747 Vacation Homes has the perfect accommodation for your stay. With top-notch amenities and convenient access to popular theme parks and entertainment venues, this institution ensures a comfortable and memorable vacation experience for all guests. Book your dream vacation home with 747 Vacation Homes today and make your stay in Kissimmee truly unforgettable.

Located at 8900 Legacy Court in Kissimmee, Florida, Go Disney Vacation is a top accommodation choice for those visiting Disney World. Offering spacious vacation home condo rentals with amenities such as a living room, dining room, fully equipped kitchen, separate bedrooms, balcony, and free WiFi, our properties provide a comfortable and affordable alternative to staying at Disney's resort hotels. With resort-style amenities, security, and a convenient location near all the major theme parks and attractions, our vacation homes offer a peaceful retreat for families looking to relax and unwind after a day at the parks. Skip the expensive dining options at Disney and enjoy preparing meals in your own kitchen. Book with us and experience the top 10 benefits of staying at a vacation home instead of a Disney resort hotel. With our high guest satisfaction ratings on TripAdvisor, Go Disney Vacation is your number one choice for a magical Disney vacation in Kissimmee, Florida.

Comfort Inn & Suites Kissimmee by the Parks is a cozy and convenient lodging option located at 7675 West Irlo Bronson Memorial Highway in Kissimmee, Florida. Situated just minutes away from popular attractions like Walt Disney World and Universal Studios, this hotel is the perfect choice for travelers looking to experience all that the area has to offer. The comfortable rooms and suites are equipped with modern amenities to ensure a relaxing stay, while the on-site facilities such as a pool, fitness center, and complimentary breakfast make for a truly enjoyable experience. Whether you're visiting for business or pleasure, Comfort Inn & Suites Kissimmee by the Parks is the ideal accommodation for your stay in the Sunshine State.

Welcome to Vivo Flex Living Kissimmee, where comfort and convenience come together in a flexible living community. Located at 4156 West Vine Street in Kissimmee, Florida, our lodging institution offers a cozy atmosphere, state-of-the-art fitness equipment, and co-working spaces to make your stay stress-free. Our modern furnishings, WiFi, and newly renovated interiors ensure that your short-term living space feels like home. Whether you're a business traveler or on vacation, our amenities cater to your needs. Enjoy lounging by the pool, meeting friends in the lobby, or getting work done in our co-working spaces.

Orbit One Vacation Villas is a charming lodging institution located at 2950 Entry Point Boulevard in Kissimmee, Florida, United States. Nestled in a peaceful and picturesque setting, this vacation villa offers a relaxing escape for guests looking to unwind and rejuvenate. The spacious and well-appointed villas provide all the comforts of home, including fully equipped kitchens, cozy living areas, and private balconies or patios. Guests can also enjoy the resort's amenities such as a swimming pool, hot tub, fitness center, and barbecue area. With its convenient location near popular attractions like Walt Disney World and Universal Studios, Orbit One Vacation Villas is the perfect choice for a memorable and enjoyable vacation experience.

Orlando Vacations Rooms is a comfortable and convenient lodging option located at 5245 West Irlo Bronson Memorial Highway in Kissimmee, Florida. Just a short drive away from the world-renowned attractions of Orlando, this institution offers cozy rooms and excellent amenities for a relaxing stay. Whether you're visiting the nearby theme parks or exploring the beautiful beaches of Florida, Orlando Vacations Rooms provides a welcoming and affordable accommodation option for your trip. Enjoy a peaceful night's sleep and easy access to all the excitement that Central Florida has to offer at this charming establishment.

Howard Johnson by Wyndham Tropical Palms Kissimmee is a charming lodging located at 4311 West Vine Street in Kissimmee, Florida, United States. This tropical-themed hotel offers comfortable accommodations with modern amenities, including free Wi-Fi, a complimentary breakfast, and an outdoor pool. The hotel is conveniently situated near popular attractions such as Walt Disney World and Universal Studios, making it the perfect choice for families and tourists looking to explore the area. With its convenient location and cozy atmosphere, Howard Johnson by Wyndham Tropical Palms Kissimmee is the ideal choice for a relaxing stay in the heart of Florida.

Breeze Kissimmee is a vibrant and lively bar located at 7 East Dakin Avenue in the heart of Kissimmee, Florida. Known for its relaxed atmosphere and friendly staff, Breeze Kissimmee offers a wide selection of beverages, including craft cocktails, beer, and wine. Guests can enjoy live music, DJ nights, and special events throughout the week. Whether you're looking for a fun night out with friends or a place to unwind after a long day, Breeze Kissimmee is the perfect spot to kick back and enjoy the breeze.

Escape to the magical world of Disney at our Water Park Heated Pool located at the Storey Lake Hideaway Club House in Kissimmee, Florida. Book directly with us for the best rates and enjoy a comfortable stay in our luxurious accommodations. Whether you're looking for a relaxing getaway or an action-packed adventure, our resort has something for everyone. Don't miss out on the opportunity to experience the magic of Disney right at your doorstep. Visit us at 4815 Love Storey Lane and make memories that will last a lifetime.

Sun Lake Rentals, LLC is a premier vacation condo rental institution located at 3164 Sun Lake Court in Kissimmee, Florida. As a real estate and travel agency, we offer spacious and well-furnished condos fully equipped with kitchens to meet all of your culinary needs. Each unit also features a large living/dining area perfect for entertainment, with amenities such as cable TV, movies, and internet access. Our vacation condo rentals are the perfect choice for a comfortable and quiet lodging experience during your Florida vacation. Just 2 miles from Disney, our location offers easy access to major restaurants, stores, and a supermarket within walking distance. Whether you are looking for a relaxing getaway or a fun-filled family vacation, Sun Lake Rentals can accommodate all of your vacation needs.

WellHome Parkside Vacation Home at Windsor Hills Resort is a luxurious lodging option located in Kissimmee, Florida. Situated at 7715 Comrow Street, this vacation home offers a tranquil and relaxing environment for guests looking to unwind and rejuvenate. As a real estate agency, WellHome Parkside Vacation Home provides guests with top-notch accommodation options, ensuring a comfortable and unforgettable stay. The resort also features a spa where guests can indulge in a variety of rejuvenating treatments and massages.

Windsor Hills Pool View Condo is a luxurious lodging option located at 7650 Comrow Street in Kissimmee, Florida, United States. This three-bedroom, two-bathroom condo is situated near Walt Disney World and offers stunning poolside views. Guests can enjoy the resort's amenities such as the clubhouse, theater, game room, and full-size gym. The condo is Disney themed throughout, with stuffed Disney characters adding to the magical atmosphere. With its proximity to popular attractions like Magic Kingdom, Epcot, and Universal Orlando, Windsor Hills is the perfect choice for a family-friendly vacation. The property is meticulously cleaned and sanitized following the guidelines of leading health agencies, ensuring a safe and comfortable stay for all guests. With its unbeatable location and top-notch amenities, Windsor Hills Pool View Condo is a popular choice for families visiting the Orlando area.

Vacation Villas at Fantasyworld Two is a lodging institution located at 4999 Kyngs Heath Road, Kissimmee, Florida. Just minutes from Orlando's famous attractions, this vacation destination offers a hometown feel with easy access to Disney World, Universal Studios, and SeaWorld. The diverse city of Kissimmee is filled with shopping, dining, and entertainment options, making it a perfect location for families and travelers of all ages. The spacious vacation rentals at Vacation Villas at Fantasyworld Two feature full kitchens, quiet bedrooms, and living areas, perfect for extended family vacations. Unique lockout units offer a private bathroom and kitchenette in the second bedroom. Onsite amenities include an outdoor swimming pool, children's pool and playground, and barbecue area.

GreenPoint Hotel Kissimmee is a charming lodging establishment located at 5245 West Irlo Bronson Memorial Highway in Kissimmee, Florida. Situated in the heart of the bustling tourist district, this hotel offers comfortable and affordable accommodations for visitors looking to explore all that Central Florida has to offer. With its convenient location near popular attractions such as Walt Disney World, Universal Studios, and SeaWorld, GreenPoint Hotel Kissimmee is the perfect home base for a memorable vacation. The hotel features spacious rooms, modern amenities, and friendly staff to ensure a pleasant stay for every guest. Whether you are traveling for business or pleasure, GreenPoint Hotel Kissimmee provides a welcoming and relaxing atmosphere for all travelers.

Wonder Vacation Homes is a premier lodging institution located at 1101 Miranda Lane in Kissimmee, Florida, United States. Our vacation homes offer a luxurious and comfortable stay for guests looking to experience the magic of the Orlando area. With spacious accommodations, modern amenities, and convenient access to popular attractions such as Disney World and Universal Studios, Wonder Vacation Homes is the perfect choice for your next getaway. Whether you're traveling with family or friends, our homes provide the ideal retreat for a memorable vacation experience. Book your stay with us today and make your vacation truly wonderful.

Nestled in the heart of Kissimmee, Florida, Orlando Vacation Rentals Homes at Storey Lake Resort offers luxurious lodging options for visitors to the area. Whether you're looking for a cozy condo or a spacious villa, this real estate and travel agency has a wide selection of vacation rentals to choose from. With its convenient location near popular attractions like Walt Disney World and Universal Studios, Storey Lake Resort is the perfect home base for your Orlando vacation. Experience the comfort and convenience of a home away from home at this beautiful resort community located at 3131 Paradox Circle.

Days Inn Kissimmee-Orlando- Hwy 192 is a charming lodging institution located at 4104 West Vine Street in Kissimmee, Florida, United States. Situated just a short drive away from popular attractions such as Walt Disney World and Universal Studios, this cozy hotel offers comfortable rooms and friendly service at an affordable price. Guests can enjoy amenities such as free breakfast, a swimming pool, and complimentary Wi-Fi during their stay. Whether visiting for a family vacation or a business trip, Days Inn Kissimmee-Orlando- Hwy 192 is the perfect choice for travelers looking for a convenient and welcoming place to stay.

Windsor Hills Kissimmee Villa is a luxurious vacation rental located at 7757 Tosteth Street in Kissimmee, Florida. This stunning villa offers guests a comfortable and stylish retreat just minutes away from the world-famous attractions of Orlando, including Walt Disney World and Universal Studios. With spacious accommodations, modern amenities, and a private pool, Windsor Hills Kissimmee Villa is the perfect choice for families and groups looking for a memorable stay in the Sunshine State. Enjoy the convenience of a fully equipped kitchen, cozy living areas, and easy access to shopping, dining, and entertainment options. Experience the magic of Florida in comfort and style at Windsor Hills Kissimmee Villa.