Search for vacation rentals in Kissimmee.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Kissimmee area to find the perfect spot for your vacay.

1514 Oak Hill Trl
	1514 Oak Hill Trl Kissimmee, FL $2,030 Vacation Rentals, Unknown  NEW! Please note that the rent amount listed does not include required leasing fees. Can you picture yourself in this home? Inside, you'll find modern lighting, carpet flooring, and plenty of living......

2178 Ranch Side Rd
	2178 Ranch Side Rd Kissimmee, FL $3,300 Vacation Rentals, Unknown  NEW! Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. This home is priced to......

1179 S Beach Cir
	1179 S Beach Cir Kissimmee, FL $2,200 Vacation Rentals, Unknown  NEW! Enjoy living in this beautiful townhome in Liberty Village, Fiesta Key Resort, Kissimmee, Florida! Fully Furnished 3 Bedrooms, 2.5 baths, and 1468 Sq ft. of living space. Has a spacious screened-in......

3984 Blossom Dew Dr
	3984 Blossom Dew Dr Kissimmee, FL $2,500 Vacation Rentals, Unknown  NEW! A beautiful big property with a familly room A living room 4 bedroom and 3 bath 3 car garage and dining room and big porch and huge patio incredible peace. A nice gated community . Beautiful drive......

1407 Lanier Point Pl
	1407 Lanier Point Pl Kissimmee, FL $2,250 Vacation Rentals, Unknown  NEW! WILL BE AVAILE at JUNE 1st. 2024 Bella Lago, Gated, a Single-Family Home 4 Bedr 2 Bathr 2 Car Garage. Lanais with lake view. Wall to Wall Carpet. Washer and Dryer included. Kitchen with granite......

608 Adriane Park Cir
	608 Adriane Park Cir Kissimmee, FL $2,995 Vacation Rentals, Unknown  NEW! Gorgeous 3/2 Pool Home with a Covered Patio and a 2 Car Garage in the Delightful Adriane Park - Kissimmee! Will be Available 6/14/24! Make sure you register on the Waiting List to be notified when......

2427 Parsons Pond Cir
	2427 Parsons Pond Cir Kissimmee, FL $2,300 Vacation Rentals, Unknown  NEW! 3/2 House for rent in Lakeside Kissimmee (1 car garage) close to schools and shopping. Fenced yard with large patio deck. Application required with proof of income. No pets allowed....

4992 Worchester Dr
	4992 Worchester Dr Kissimmee, FL $2,700 Vacation Rentals, Unknown  NEW! New Amazing Property with lake view, Welcome to your dream home! These 3 bedrooms, 2-bathroom property boasts beautiful finishes and top-of-the-line appliances new. The is open floor plan, 9'4"......

915 Sumner St
	915 Sumner St Kissimmee, FL $2,200 Vacation Rentals, Unknown  NEW! Ready for immediate move in! Townhouse located in downtown Kissimmee. Front porch enters into a large living room. Hallway through to kitchen includes a half bathroom and storage closet. Kitchen......

1891 Windward Oaks Ct
	1891 Windward Oaks Ct Kissimmee, FL $2,600 Vacation Rentals, Unknown  NEW! Live in a home with tall 11 ft ceilings with large tiled wet area and open floor plan view from the kitchen. Have your CABLE paid for and live in a spacious waterfront view home in a secure GATED......

3958 Carrick Bend Dr
	3958 Carrick Bend Dr Kissimmee, FL $2,800 Vacation Rentals, Unknown  NEW! This beautiful lakeview single-family home is located in the resort-style gated community of Bellalago. It offers four bedrooms, two bathrooms, a gourmet kitchen, a spacious Dining room, a living......

407 Iris St
	407 Iris St Kissimmee, FL $4,980 Vacation Rentals, Unknown  NEW! A MUST SEE - Executive 4 Bedroom 3 bath Home with Garage located in the Heart of Celebration's Main Village. Recently painted throughout the interior, this beautiful home features Granite......

8809 Grand Palms Cir #B
	8809 Grand Palms Cir #B Kissimmee, FL $1,750 Vacation Rentals, Unknown Check out this spacious lovely 3-bedroom, 2-bathroom second-floor condo nestled in the desirable Grand Palms community. With a serene private view overlooking wooded areas, this condo boasts both a......

3284 Falcon Point Dr
	3284 Falcon Point Dr Kissimmee, FL $2,990 Vacation Rentals, Unknown 4 bedrooms 2.5 bathroom home near Hunter's Creek and is a 5 min drive (20-30 min walk) from The Loop, where there are numerous shops, restaurants and entertainment. The home offers a 2 car garage,......

2419 Ashecroft Dr
	2419 Ashecroft Dr Kissimmee, FL $1,970 Vacation Rentals, Unknown Please note that the rent amount listed does not include required leasing fees. Find yourself in this beautiful home! This home features luxury vinyl plank flooring, an open living area and large......

1357 Boulder Dr
	1357 Boulder Dr Kissimmee, FL $2,060 Vacation Rentals, Unknown Please note that the rent amount listed does not include required leasing fees. Don't miss out on this charming home! Inside, you'll find plenty of living space to spread out and make memories as......

2127 Caribbean Dr N
	2127 Caribbean Dr N Kissimmee, FL $1,600 Vacation Rentals, Unknown Ground Level 2 Bedroom 2 Bathroom Condo with 1 Parking in Front and more in the Center Parking, Block construction with fenced in patio with concrete flooring. Carpet Master Guest and Living Room......

9128 Westside Hills Dr
	9128 Westside Hills Dr Kissimmee, FL $2,900 Vacation Rentals, Unknown Welcome to the brand-new listing! It is with great pleasure that we present this pristine, newly constructed home in the heart of Central Florida, an area renowned for its perfect blend of serene......

1799 Hideout St
	1799 Hideout St Kissimmee, FL $2,500 Vacation Rentals, Unknown Beautiful new build home in the heart of Kissimmee. The home features 3 bedrooms and 2 bathrooms and a open main living area. The home also features indoor laundry and a 2 car garage. Located only......

Santee Dr
	Santee Dr Kissimmee, FL $3,950 Vacation Rentals, Unknown Very comfortable, nice, clean 5 bed 4 bath home with built in pool and spa. Quiet neighborhood has 2 parks and 2 ponds with sidewalks around both. Tile in the main living areas with vinyl plank in......

3119 Mandolin Dr
	3119 Mandolin Dr Kissimmee, FL $2,225 Vacation Rentals, Unknown Please note that the rent amount listed does not include required leasing fees. You will love making this beautiful house your new home! The front exterior boasts a two-car garage, a covered......

4384 Spring Blossom Dr
	4384 Spring Blossom Dr Kissimmee, FL $2,299 Vacation Rentals, Unknown Coming soon! THIS HOME IS CURRENTLY BEING ENJOYED BY ANOTHER RESIDENT, BUT WILL BE AVAILABLE SOON. PLEASE RESPECT THEIR PRIVACY AND DO NOT DISTURB. Take a look at this beautiful home featuring 3......

Heatherstone Dr
	Heatherstone Dr Kissimmee, FL $1,200 Vacation Rentals, Unknown STUDIO FOR RENT! Is not gonna last. Welcome to your cozy retreat in the heart of Kissimmee. This charming studio apartment offers everything you need for comfortable urban living. Utilities......

3851 Wood Thrush Dr
	3851 Wood Thrush Dr Kissimmee, FL $2,350 Vacation Rentals, Unknown Welcome to your rental home in the charming gated community of Spring Lake Village! This lovely single-family residence boasts three bedrooms and two baths, offering both comfort and functionality.......

29 W Country Cove Way
	29 W Country Cove Way Kissimmee, FL $1,550 Vacation Rentals, Unknown Welcome to this amazing rental property situated in a peaceful and quiet neighborhood just a stone's throw away from BVL Blvd. Located just minutes away from Osceola Parkway and other major......

1786 Neptune Rd
	1786 Neptune Rd Kissimmee, FL $1,000 Vacation Rentals, Unknown Studio Apartment located on the back of the main house, private entrance. Electricity, Internet, and Water Included, Kitchen, dining, living room combo, separate bedroom. Comes with electric......

1410 Orchid Ln
	1410 Orchid Ln Kissimmee, FL $1,905 Vacation Rentals, Unknown Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. This home features......

4080 Navigator Way
	4080 Navigator Way Kissimmee, FL $2,500 Vacation Rentals, Unknown 2948 sf, four bedroom, three bath and two car garage home with pond view. New paint and carpet provides a beautiful blank canvas that will match your decor. Large kitchen with solid surface counter......

1200 Pensacola Ct
	1200 Pensacola Ct Kissimmee, FL $2,500 Vacation Rentals, Unknown Now available for rent! This spacious townhouse is nestled within the beautiful gated community of Heritage Run. Boasting 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home offers a......

3051 Winding Trl
	3051 Winding Trl Kissimmee, FL $2,500 Vacation Rentals, Unknown 4 bedroom, 2 bath home in gated community of Bellalago. 24 hour security. 3 pools, fitness center, access to Lake Toho. Spacious interior offers split plan with living, dining and family areas.......

2810 Club Cortile Cir #B
	2810 Club Cortile Cir #B Kissimmee, FL $1,995 Vacation Rentals, Unknown Spacious 3 bedroom 2 bath 2nd floor condo with open floor plan, eat in kitchen, and breakfast bar, located in a gated community, comm pool, fitness center and tennis courts No pets per HOA Tenant......

2703 Rismen Ct
	2703 Rismen Ct Kissimmee, FL $2,600 Vacation Rentals, Unknown No rear neighbors located on oversize lot. 4 bedroom, 2 bath, with larger 2 car garage. Covered screen porch. Open floor plan ideal for entertaining. No carpet in property, and huge master bedroom......

623 Moss Park Ct
	623 Moss Park Ct Kissimmee, FL $2,385 Vacation Rentals, Unknown Please note that the rent amount listed does not include required leasing fees. Find yourself in this beautiful home! This home has an open living space filled with natural light and lined with......

3101 Duxbury Dr
	3101 Duxbury Dr Kissimmee, FL $2,495 Vacation Rentals, Unknown AVAILABLE MAY 1ST! Welcome home to luxury living at its finest! Nestled in a serene neighborhood, this stunning 4-bedroom, 2.5 bathroom home boasts tile and vinyl flooring throughout. The heart of......

3131 Linton Rd
	3131 Linton Rd Kissimmee, FL $2,315 Vacation Rentals, Unknown Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. This home features......

4475 Biscayne Breeze Way
	4475 Biscayne Breeze Way Kissimmee, FL $3,000 Vacation Rentals, Unknown Beautiful spacious home nestled on a private water view offering gorgeous sunsets. Open layout concept great for entertaining, kitchen overlooks the nook and casual family room with direct access......

1181 Spokane Point
	1181 Spokane Point Kissimmee, FL $2,680 Vacation Rentals, Unknown We make Pre-Leasing easy! Apply now and, once you're approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is......

Plumwood Cir
	Plumwood Cir Kissimmee, FL $1,200 Vacation Rentals, Unknown Beautiful 2020 Trailer for rent for a single working individual non smoker prefer. It has a kitchenette area with full size refrigerator stove, microwave cabinets double sink and more it has food......

1989 Egret Meadow Ave
	1989 Egret Meadow Ave Kissimmee, FL $2,700 Vacation Rentals, Unknown Nice house for rent empty house with stove in refrigerator...

823 Oak Shadows Rd
	823 Oak Shadows Rd Kissimmee, FL $6,500 Vacation Rentals, Unknown Reduced price! Beautiful located in Celebration FL. The main House has 5 Bedrooms 3 full bathrooms, 2 car garage, 2 huge balconies, a private nice size patio to enjoy your BBQ or family gatherings......