Paradise Cay Homes with Pool

Paradise Cay Homes with Pool

Welcome to Paradise Cay, a charming subdivision located in the heart of Kissimmee, FL. This delightful community is nestled in Osceola County, offering a tranquil and family-friendly atmosphere for residents to enjoy.

One of the standout features of the homes in Paradise Cay is the option for a private pool. Imagine coming home to your own oasis, where you can relax and unwind in the refreshing waters or host memorable poolside gatherings with friends and family. The homes with pools in Paradise Cay truly elevate the Florida living experience, providing a perfect retreat right in your backyard.

Beyond the allure of private pools, Paradise Cay boasts a convenient location with easy access to local amenities, shopping, dining, and entertainment options. Residents can also take advantage of being just a short drive away from world-famous theme parks and attractions, making it an ideal choice for both primary homeowners and vacation property investors.

Whether you're looking for a permanent residence or a vacation getaway, Paradise Cay offers a wonderful blend of comfort, convenience, and leisure. Explore the available homes with pools in Paradise Cay and discover the perfect place to call home in sunny Kissimmee, FL.

Newest Paradise Cay Homes with Pool

$275,000
3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code
Beautiful and spacious 3 bedroom, 3 bathroom townhouse in the GATED COMMUNITY of PARADISE CAY. This LARGER UNIT boasts 1,362 square feet under A/C and features an OPEN FLOOR PLAN with a recently UPGRADED kitchen including GRANITE COUNTERTOPS and FRESHLY PAINTED CABINETS. With 2 BEDROOMS and 2 FULL bathrooms upstairs, and a MASTER BEDROOM WITH FULL BATH ON THE FIRST FLOOR, this home is perfect for families. ALL APPLIANCES ARE NEW OR HAVE BEEN PURCHASED SINCE MARCH 2023 including the dryer, washer, refrigerator, garbage disposal, water heater, and AC/heating unit except for the stove and dishwasher, which were already new when the current owners purchased the home. All bedroom windows have blinds and curtains, while the living room window and patio have blinds. Located within WALKING DISTANCE to US 192, residents will enjoy easy access to restaurants, grocery stores, and other convenient stores. Paradise Cay is a Mediterranean-style community just 4 miles from the Disney main gate, offering a pool, cabana, and playground area for residents to enjoy making this home a great investment opportunity or a comfortable primary residence.

5315 Paradise Cay Circle, Kissimmee
$275,000
3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code
LOCATION, UPDATES & INVESTMENT POTENTIAL! Welcome to this beautifully updated 3-bedroom, 3-bathroom home in the gated community of Paradise Cay, ideally located just 15 minutes from Walt Disney World and Orlando’s world-famous attractions. Whether you’re looking for an investment property, vacation home, or primary residence, this home offers an exceptional combination of location, amenities, and recent improvements. The desirable split-bedroom floor plan provides privacy and functionality, while the small, private backyard area offers a comfortable space to relax or entertain. Major updates include a new A/C system installed in March 2026, plus a new dishwasher, range, refrigerator, water heater, and flooring, all completed in May 2026. Enjoy resort-style living within the gated community, featuring a community pool, tennis courts, spa, pickleball, shuffleboard, bocce ball, BBQ area, clubhouse, and fitness center. The location is truly a standout feature—approximately 15 minutes to Walt Disney World and conveniently close to Orlando’s world-renowned theme parks, attractions, dining, shopping, entertainment, and major roadways. This prime location makes the property especially appealing to both long-term and vacation-oriented investors. The property has an established rental history- an additional appeal for investors. With its recent upgrades, flexible floor plan, extensive community amenities, and unbeatable proximity to Disney and the attractions, this property is an excellent opportunity for an investor, second-home buyer, or family looking to enjoy the best of the Central Florida lifestyle.

5340 Paradise Cay Circle, Kissimmee
$270,000
3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code
Welcome to this beautifully maintained 3-bedroom, 3-bath townhome in the desirable gated community of Paradise Cay in Kissimmee. Thoughtfully designed across two levels, this home offers a versatile floor plan with a first-floor bedroom and full bath, ideal for guests, a home office, or added privacy. The second floor features two spacious bedrooms, each with its own full bathroom, along with a convenient laundry area. The well-appointed kitchen offers ample cabinetry, full-size appliances, and a comfortable dining area, creating a functional space for everyday living and entertaining. Enjoy the privacy and convenience of a gated community with access to a community pool and playground. Ideally located just off US-192, the property is minutes from Walt Disney World and other Central Florida attractions, while also offering easy access to Celebration, shopping, dining, entertainment, and major roadways. Whether you're looking for a primary residence, a Florida getaway, or an investment property, this townhome offers an excellent combination of location, functionality, and lifestyle. A wonderful opportunity in the heart of Kissimmee—schedule your private showing today!

5276 Paradise Cay Circle, Kissimmee
$295,000
3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code
Virtually Staged. Welcome to this beautifully updated 3-bed 3-bath 1595 sq ft townhome located in the desirable gated community of Paradise Cay in Kissimmee—where modern upgrades, prime location, and investment potential come together. Property Highlights: End Unit with more lights. The largest floor plan in the community Fully renovated interior with stylish laminate flooring throughout New counter top for kitchen and bathroom Fresh interior paint for a bright, clean look in neutral color Recent upgrades (2025): New AC, top load washer, and 5 burner electric range (2024): new microwave; LG dryer Large parking space for handicap parking Community Features: Secure gated access Resort-style amenities including pool, playground, and scenic walking trails HOA covers exterior maintenance, trash service—offering truly low-maintenance ownership Unbeatable Location: Less than 3 miles to Walt Disney World Minutes to US-192, with easy access to I-4 and Orlando premium outlet and orange convention center Close to world-class golf, shopping, dining, and entertainment Investment Opportunity: Zoned for short-term and long-term rentals—perfect as a primary residence, vacation home, or income-producing property Live, vacation, or invest in one of Central Florida’s most sought-after areas. Schedule your private showing today and start enjoying the Florida lifestyle!

5266 Paradise Cay Circle, Kissimmee
$269,000
3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code
This well-maintained property features a functional floor plan with spacious bedrooms and three full bathrooms, offering comfort, flexibility, and ample space for both residents and guests. Located within a gated, short-term rental-friendly community, the home is an excellent choice for primary homeowners, vacation-home buyers, or investors. Additional highlights include a low HOA fee, one assigned parking space, and access to desirable community amenities, including a swimming pool and park. Ideally situated just 10–14 minutes from the Walt Disney World® theme parks, the property offers exceptional convenience with nearby shopping centers, restaurants, hospitals, pharmacies, schools, and major highways. Whether you're searching for a primary residence, a vacation retreat, or an income-producing investment, this property presents an outstanding opportunity to own in one of Central Florida's most sought-after destinations.

5390 Paradise Cay Circle, Kissimmee
$279,000
3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code
LOCATION, LOCATION, LOCATION! Beautiful fully furnished 3-bedroom, 3-bath townhouse located in a desirable gated community with NO lease restrictions — perfect for short-term rentals, long-term rentals, Airbnb, or Vrbo investment opportunities. Features 1 assigned parking space and access to community amenities including a pool and park. Ideally located just 10–14 minutes from Disney Theme Parks and close to shopping malls, restaurants, hospitals, pharmacies, and top-rated schools. Excellent opportunity for investors or vacation homeowners seeking strong rental income potential!

5520 Paradise Cay Circle, Kissimmee
$273,990
3 Beds ⋅ 3 Baths ⋅ Paradise Cay SubDv. ⋅ 34746 Zip Code
FULLY FURNISHED. Beautiful 3-bedroom, 3-bathroom townhome located in a secure gated community, offering the perfect blend of comfort, convenience, and investment potential. This well-maintained property features a functional floor plan with spacious bedrooms and three full bathrooms, ideal for both residents and guests. The community allows short-term rentals, making this property a rare and highly desirable opportunity for buyers seeking flexibility. Recently operated as a successful Airbnb, the home already has confirmed bookings and an excellent reservation history, creating a true turnkey investment ready to produce income from day one. With a low HOA, this property is not only perfect for investors but also an outstanding choice for first-time homebuyers looking for affordability without compromising on location or amenities. The home is being sold fully furnished, ensuring a seamless transition whether you plan to continue renting, use it as a vacation getaway, or move in immediately. Centrally located with easy access to major theme parks, shopping centers, hospitals, and highways, residents enjoy both convenience and the security of a gated community in a highly desirable location.

5210 Paradise Cay Circle, Kissimmee
Start Your Search