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Luxury Houses for Rent in Kissimmee, FL

75 rentals

2686 Chantilly Ave - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Kissimmee

Townhouse - KISSIMMEE, FL

2686 Chantilly Ave, Kissimmee, FL 34741

Luxury | Balcony | Swimming pool

3 beds

2 baths

$2,750

House for rent

Modern Townhouse with Resort-Style Amenities

Experience the charm of this spacious 3-bedroom, 2.5-bath townhouse featuring an open concept kitchen perfect for gatherings. Sunlight fills the airy rooms, while the private balcony offers a serene spot to unwind. Enjoy resort-style living in Tapestry with a sparkling pool, fitness center, and community security. Conveniently located near The Loop and Disney, this corner unit is not just a home but a vibrant lifestyle waiting for you!

2647 Horseshoe Bay Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

2647 Horseshoe Bay Dr, Kissimmee, FL 34741

Luxury | Walk-in closets | In-unit laundry

2 beds

2 baths

$2,150

House for rent

Waterfront Haven with Inviting Open Layout

This stunning 2-bedroom, 2-bathroom home features breathtaking water views and an abundance of natural light. The open floor plan is perfect for entertaining, leading to a charming screened porch where mornings can be enjoyed overlooking the serene pond. With convenient access to shopping, dining, and entertainment, this move-in ready retreat offers a fabulous lifestyle. Don’t miss the chance to unwind on the scenic pond trail right outside your door!

9066 Beach Tea Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

9066 Beach Tea Way, Kissimmee, FL 34747

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,800

House for rent

Modern 4-Bed Oasis with Resort Amenities

Newly built in 2023, this stunning 4-bedroom, 3-bath home spans 2,206 sq. ft. and features a bright open floor plan with split bedrooms. The kitchen boasts stainless steel appliances and a spacious walk-in pantry. The luxurious master bath includes dual sinks, a large shower, and a walk-in closet. Enjoy the convenience of a 2-car garage and resort-style amenities, including a pool, clubhouse, and playground, all in a prime location near shopping and I-4 access.

Adriatico Lane #1 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Kissimmee

Adriatico Lane - 1

Adriatico Lane #1, Kissimmee, FL 34747

Luxury

Studio

1 bath

$3,495

House for rent

Available Oct 1

Luxurious Townhome with Private Splash Pool & Themed Rooms

Experience luxury living in this stunning 5-bedroom, 4.5-bath townhome, beautifully furnished for long-term enjoyment. Highlighted by an open-concept design, modern kitchen, and a bonus loft, it’s perfect for family gatherings. Enjoy the themed kids' rooms and relax in the private splash pool. Located in a resort community, residents have access to incredible amenities just minutes away from Walt Disney World and major attractions.

3125 Simpson Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

3125 Simpson Rd, Kissimmee, FL 34744

Luxury | Storage | Garage parking

Studio

1 bath

$1,100

House for rent

Modern Efficiency Studio in Quiet Neighborhood

Newly built efficiency studio perfect for privacy and convenience. This compact space features a full-size bed, modern kitchen with two-burner stovetop, and a private bathroom. Enjoy dedicated air conditioning for comfort. Move-in ready and designed for clean, simple living! Ideal for anyone looking for a cozy retreat.

1785 Lisa Ln #1785 - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - Kissimmee, FL

1785 Lisa Ln #1785, Kissimmee, FL 34744

Luxury | Swimming pool | Garage parking

3 beds

3 baths

$3,500

House for rent

En-suite Pool Home with Smart Features & Dock Access

This stunning pool home in Breckenridge features en-suite bedrooms ensuring comfort and privacy for all. The expansive master suite boasts two closets and a lavish bathroom with a garden tub and tiled shower. Relax by one of two fireplaces or take a swim in the private pool. Recent upgrades include a brand-new roof, remodeled kitchen with granite countertops, and smart home technology. Enjoy the convenience of serene outdoor living with a dock for water activities.

2990 Salted Rim Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

2990 Salted Rim Rd, Kissimmee, FL 34747

Luxury | Swimming pool | Fitness center

4 beds

4 baths

$3,900

House for rent

Spacious 4-Bed Home with Resort-Style Amenities

This stunning three-story model features 4 bedrooms, each with en suite baths, and an expansive open floor plan. Enjoy the Florida sunshine on large balconies, or relax in a tropical backyard with shell pathways. Rent includes cable, internet, and access to the Fins Up Beach Club with pools and a gym, all within minutes of Disney parks. Upgraded appliances, quartz countertops, and a tankless water heater enhance modern living in this resort-style community.

1775 Harbor Road - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

4/2

1775 Harbor Road, Kissimmee, FL 34746

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$3,750

House for rent

Family-Friendly Retreat with Shared Amenities

This fully furnished 4-bedroom, 2-bath home comfortably sleeps 13, perfect for family gatherings or group getaways. The spacious layout includes a primary suite with a king bed and private bathroom, plus a game room featuring a full daybed and bunks. Enjoy a 2.5-acre rural lot with shared playgrounds, dog parks, and firepits. Professionally cleaned and sanitized, this home offers a comfortable stay with modern conveniences and plenty of outdoor space for fun and relaxation.

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1796 Tohoqua Blvd #1796 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Kissimmee

3 BR, 3 BA in Kissimmee

1796 Tohoqua Blvd #1796, Kissimmee, FL 34744

Luxury | Walk-in closets | In-unit laundry

3 beds

3 baths

$2,700

House for rent

Available Nov 30

Bright Townhome with Resort-Style Amenities

This spacious 3-bedroom, 2.5-bath townhome features modern finishes with an open-concept layout, quartz countertops, and stainless steel appliances. Enjoy a master suite with a walk-in closet and smart-home features like keyless entry. Located in the desirable Tohoqua community, residents have access to a swimming pool, fitness center, and scenic walking trails, making this a perfect blend of comfort and convenience.

3135 Enclave Ct - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Kissimmee

Townhouse - KISSIMMEE, FL

3135 Enclave Ct, Kissimmee, FL 34746

Luxury | In-unit laundry | Ceiling fan

2 beds

2 baths

$1,750

House for rent

Modern Townhome with Renovated Kitchen & En-Suites

Move-in ready and beautifully updated, this spacious 2-bedroom, 2.5-bath townhouse features a renovated kitchen with quartz countertops and new cabinets. Each bedroom has a full en-suite bath for added convenience. The bright main level includes a half bath for guests. Enjoy fresh, modern flooring throughout the upstairs. This well-maintained home is perfect for immediate occupancy, plus a $500 move-in credit is offered with a 15–18-month lease.

4445 Shiva Loop - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

4445 Shiva Loop, Kissimmee, FL 34746

Luxury | Walk-in closets | Swimming pool

1 bed

1 bath

$1,200

House for rent

Luxurious 8-Bedroom Oasis with Private Pool & Game Room

This stunning 8-bedroom, 6-bathroom luxury home spans 3,565 sq. ft. and offers a perfect blend of elegance and entertainment. Features include a chef-inspired kitchen with quartz countertops, a spacious family area, and an oversized lanai with a screen-enclosed pool and spa. The converted garage doubles as a game and arcade room, making it perfect for family fun. Fully furnished and designed for comfort, this residence is a dream retreat in Florida's paradise.

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2010 Spring Shower Cir - Photo 1 of 1
Age restricted

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

2010 Spring Shower Cir, Kissimmee, FL 34744

Luxury | Walk-in closets | Swimming pool

3 beds

3 baths

$2,950

House for rent

Luxurious Living in 55+ Tohoqua Reserve

Explore 2,175 sq. ft. of elegance in this stunning 3-bed, 3-bath home designed for modern 55+ living. With an open-concept layout, a chic gourmet kitchen with Quartz countertops, and a vast great room, this residence ensures comfort and style. The primary suite offers a serene retreat, while the community boasts a resort-style pool, fitness center, and vibrant social spaces. Ideal location near amenities and Orlando attractions.

8049 Dreamsicle Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

8049 Dreamsicle Dr, Kissimmee, FL 34747

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$3,300

House for rent

Resort-Style Living with All-Inclusive Amenities

Embrace a lifestyle of leisure in this stunning 2-bedroom, 2.5-bath home within Margaritaville Resort. Spanning 1,217 SqFt, this vibrant residence boasts a modern open layout and a tropical-inspired backyard. Enjoy hassle-free living with included utilities, cable, internet, and expert maintenance. Long-term leases offer exclusive perks such as access to pools, a fitness center, and dining credits. Perfectly located near Disney and Universal, every day feels like a getaway!

2505 Hybrid Ct - Photo 1 of 1

5d+ ago

Luxury Cresent Lakes house for rent in Kissimmee

Single Family Residence - Kissimmee, FL

2505 Hybrid Ct, Kissimmee, FL 34758

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,500

House for rent

Modern Oasis with Pool in Peaceful Community

This beautifully updated 3-bedroom, 2-bath home boasts an open floor plan and a modern kitchen, perfect for entertaining. The private fenced pool with spa offers a serene retreat. The primary suite features a walk-in closet and en-suite bath for added comfort. Nestled on a quiet cul-de-sac, enjoy easy access to shopping, dining, and Orlando attractions from this 1,480 sq ft haven in the charming Crescent Lakes community.

1612 Columbia Arms Cir #239 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Kissimmee

Ready. 1 Bed 1 bath 2nd floor apartment.

1612 Columbia Arms Cir #239, Kissimmee, FL 34741

Luxury | Walk-in closets | Swimming pool

1 bed

1 bath

$1,400

House for rent

Available Nov 1

Spacious Townhouse with Vaulted Ceilings & Pool

Experience comfort in this impressively spacious 1-bedroom, 1-bath townhouse featuring a cathedral ceiling living room and cozy office space flooded with natural light. The bedroom includes a walk-in closet, while the well-appointed kitchen comes with a gas stove and modern appliances. Enjoy a friendly, gated community with amenities like a gym and pool, plus convenient access to shopping and attractions. Ideal for those seeking tranquility close to vibrant entertainment options.

5020 W Irlo Bronson Memorial Hwy - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

5020 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746

Luxury | Assigned parking | Elevator

Studio

1 bath

$799

House for rent

Cozy Studio Near Disney with Modern Touches

This compact yet stylish studio in Kissimmee is perfect for those seeking simplicity and convenience. Enjoy premium vinyl plank flooring and a full bathroom in a cozy 350 sq ft space. Located moments from Disney, it offers great access to eateries and shopping. One dedicated parking spot and basic Wi-Fi included enhance the living experience. Perfect for food lovers and shopaholics, this unit is ready to welcome you home!

2339 Neptune Rd #A - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

2339 Neptune Rd #A, Kissimmee, FL 34744

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,799

House for rent

Elegant Lakefront Retreat with Luxurious Touches

Experience refined living in this fully furnished 3-bedroom, 2.5-bath home. With 2,750 sq ft, it features a chef’s kitchen with dual ovens, a spacious master suite with a spa bath, and a game room. Enjoy serene views of Fish Lake from the screened porch or private pier. Luxuries include utilities included and vibrant outdoor activities like kayaking and fishing. This lakefront haven perfectly blends relaxation and fun, making it a lifestyle choice beyond just a rental.

7939 Sea Pearl Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Single Family Residence - KISSIMMEE, FL

7939 Sea Pearl Cir, Kissimmee, FL 34747

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,500

House for rent

Luxurious Pool Home in Ideal Location

This stunning two-story, 5-bedroom, 4-bath pool home features an open-concept kitchen with an island and breakfast nook, perfect for entertaining. The primary suite boasts French doors leading to the heated pool, a jetted tub, and a walk-in shower. Enjoy seamless indoor/outdoor living with a spacious backyard and a converted game room. Nestled in a gated community, this home is just moments from Disney, shops, and restaurants, making every day feel like a vacation.

2774 Corvette Ln - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Kissimmee

Townhouse - KISSIMMEE, FL

2774 Corvette Ln, Kissimmee, FL 34746

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$2,800

House for rent

Resort-Style Townhome Minutes from Disney Magic

Experience the perfect blend of comfort and convenience in this updated 3-bedroom, 2.5-bath townhome. Featuring an open-concept layout and a modern kitchen with quality appliances, this fully furnished home offers a downstairs bedroom and bath for easy living. Enjoy your private screened-in patio and access to fantastic amenities like a lagoon-style pool, fitness center, and 24-hour security. Ideal for both seasonal and long-term stays in a prime location near Disney!

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7055 Big Bend Dr - Photo 1 of 1

5d+ ago

Luxury Bay Lake Ranch house for rent in Kissimmee

Single Family Residence - ST CLOUD, FL

7055 Big Bend Dr, Kissimmee, FL 34771

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,800

House for rent

Exquisite Custom Home with Spacious Outdoor Areas

Nestled on an acre in Bay Lake Ranch, this stunning 3-bedroom, 2.5-bathroom custom home features a welcoming foyer, open living space with a fireplace, and a kitchen equipped with stainless steel appliances. The primary suite boasts a luxurious en-suite bathroom with a jetted tub and double walk-in closets. Enjoy a bonus room perfect for an office or play area, plus additional loft space upstairs. With front and rear porches, this home is ideal for enjoying the serene outdoor environment.

7809 Beechfield St #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Magical Adv 5 Star Villa Movie Room Arcade Pool and More

7809 Beechfield St #NA, Kissimmee, FL 34747

Luxury | Balcony | Swimming pool

6 beds

4 baths

$7,999

House for rent

Available Jul 23

Enchanting 6-Bedroom Villa Near Disney Magic

Experience a magical getaway in this updated 6-bedroom, 4-bath home offering 2,812 sq ft of fun! The highlight is a private pool, along with a thrilling Star Wars gaming center and home theater. Located in a gated resort community just 1.5 miles from Disney, enjoy amenities like water slides and tennis courts. With dedicated entertainment spaces and modern comforts, this villa is perfect for families seeking an unforgettable vacation experience.

2608 Bowring St #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Jedi Training Camp Top Rated 5 Star Villa

2608 Bowring St #NA, Kissimmee, FL 34747

Luxury | Balcony | Swimming pool

5 beds

5 baths

$7,999

House for rent

Available Jul 23

Epic 5-Bed Villa with Private Pool & Game Room

This newly remodeled 5-bedroom, 5-bath home is just 1.5 miles from Disney World, combining adventure and relaxation. Enjoy the private heated pool, spa, and a state-of-the-art game room with immersive features. The outdoor patio boasts a TV for fun al fresco gatherings. With resort-like amenities and ample space for 12 guests, this is the ultimate family-friendly getaway in a secured, scenic community. Perfect for creating unforgettable memories!

7759 Teascone Blvd #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

Ultimate Adventure Villa Top Rated 5 Star Disney more

7759 Teascone Blvd #NA, Kissimmee, FL 34747

Luxury | Balcony | Swimming pool

4 beds

5 baths

$7,999

House for rent

Available Jul 23

Ultimate Adventure Villa with Game Room & Theater

Experience the thrill of vacationing in this luxurious 4-bedroom villa that accommodates 11 guests. Located just 2 miles from Disney, this home features the best-rated game room in Windsor Hills, a private movie theater, and themed kids' rooms. Enjoy outdoor fun with a private pool and spillover spa, while resort amenities include community pools, a gym, and more. Perfect for families seeking unforgettable adventures!

2508 Hassonite St - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Kissimmee

2508 Hassonite St, Kissimmee, FL 34744

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$1,900

House for rent

Upgraded Townhome with Poolside Views & Style

This beautiful 2-bedroom, 2.5-bathroom townhome features modern upgrades throughout, including a stunning kitchen with glass top stove and 42" cabinets. The master bath boasts a garden tub and walk-in closet, while the 2nd bath offers a luxurious "soaker tub." Enjoy energy-efficient features and plenty of storage, all while relaxing by the community pool with serene water views. Perfect for a vibrant lifestyle in a gated community.

3800 Sonoma Blvd #10 - Photo 1 of 1

5d+ ago

Luxury house for rent in Kissimmee

3800 Sonoma Boulevard - 10

3800 Sonoma Blvd #10, Kissimmee, FL 34741

Luxury

1 bed

1 bath

$900

House for rent

Available Jan 1

Private Room Suite Near Disney Attractions

Rent a cozy private room with an en-suite bathroom starting at $800, utilities included! Located just minutes from Disney Springs™ and top attractions, this suite is ideal for quick move-ins. Enjoy shared access to a sparkling private pool and deck, perfect for those warm Florida days. An excellent opportunity for building credit history since monthly rent payments are reported to major credit bureaus. Quick approval process makes this an easy choice for comfortable living!

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Home > House Rentals in Kissimmee > Kissimmee Luxury Houses For Rent
Updated: January 24, 2026

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