Margaritaville, Rolling Oaks Townhomes for Sale in Kissimmee - 25 townhouses

Remarks: One or more photo(s) has been virtually staged. Welcome to 2915 Castaway Ln, a gated, 3-bedroom, 3-bathroom two-story townhome located in the Rolling Oaks community of Kissimmee. The monthly HOA covers a wide range of services, including common area landscaping, bulk cable, internet and telephone, annual termite inspection and baiting, valet trash collection, community security, and building insurance that includes full roof replacement. Rolling Oaks is zoned for short-term rentals, while also allowing mid- and long-term leases, as well as full-time residency. Within the community, you’ll find a small playground, dog park, and Adirondack seating area. While the neighborhood itself keeps amenities minimal, residents and guests have access to the nearby Margaritaville Fins Up Beach Club for an additional fee. Located just minutes from US-192, this property places you approximately 20 minutes from Walt Disney World and about 35 minutes from Universal Orlando. Dining, shopping, and entertainment options, including Margaritaville Resort and Sunset Walk, are all close by. Enjoy! *Some marketing images have been AI-assisted and virtually staged to illustrate the property’s potential layout, design, use of space, and possible aesthetic enhancements. Certain photos may include digitally enhanced visualization of furnishings, décor, finishes, landscaping, or cosmetic elements for marketing and illustrative purposes only. Actual property conditions, features, finishes, fixtures, and appearance may vary, and buyers are encouraged to independently inspect the property to verify all present conditions.*

Listing is courtesy of: PROFESSIONAL REAL ESTATE TEAM (407-483-4964)

Listing Agent: Jany Perez (407-483-4964)

Remarks: CURRENTLY LEASED FOR $3,000 PER MONTH THROUGH 5/10/27. LEASE CAN BE TRANSFERRED TO NEW BUYER! SPECTACULARLY FURNISHED VILLA AVAILABLE FOR SALE AT MARGARITAVILLE RESORT ORLANDO! This Home Features 2 BEDROOM, 2.5 BATH and a BONUS BEDROOM! Kitchen with Quartz Countertops, Island with Seating, Stainless Steel Appliances, Washer and Dryer and Abundant Natural Light, Each of the Bedrooms has Ceiling Fans. One Bathroom has a Shower/Tub Combo. The Door from the Kitchen Leads you to a Beautiful Patio, Lounge Chairs and Tropical Landscaping, Palm Trees, and Tropical Foliage. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Great Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Under contract-accepting backup offers. Position your portfolio for success with this premier short-term rental opportunity at 8189 Surf Street in Margaritaville Resort Orlando. Located within one of Central Florida’s most recognized vacation rental destinations, this fully furnished 2-bedroom, 2.5-bath villa offers a true turnkey investment—professionally designed, impeccably maintained, and ready to generate immediate rental income. Thoughtfully designed to maximize guest appeal and occupancy, the villa features a bright open-concept floor plan, soaring ceilings, quartz countertops, upgraded appliances, and premium coastal finishes throughout. The private patio overlooking a tranquil pond creates an inviting outdoor retreat—an amenity highly valued by vacation guests seeking relaxation after a day at the parks. The home is delivered fully furnished with the upgraded Margaritaville Furniture Package, eliminating startup costs and ensuring seamless onboarding into the resort’s rental program. Owners and guests enjoy access to a full suite of resort-style amenities, including multiple pools, on-site restaurants, live entertainment, a fitness center, kids’ club, and the popular Fins Up Beach Club. The resort’s prime location—just minutes from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando—drives consistent year-round tourism demand, while on-site attractions like Island H2O Live! Water Park further enhance guest experience and booking potential. Nearby, Promenade at Sunset Walk offers walkable dining, retail, and entertainment options that increase guest satisfaction and repeat stays. Backed by the strength of the Margaritaville brand and situated in one of the highest-performing vacation rental corridors in the country, this property represents a compelling opportunity for investors seeking strong occupancy, premium nightly rates, and long-term appreciation potential. Capitalize on a proven short-term rental model in a high-demand market—schedule your private showing today.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Nick Whitehouse (407-902-4639)

Remarks: Turnkey 4BR/3BA townhome in Margaritaville Resort Orlando! Fully furnished and thoughtfully designed with an open-concept layout, modern coastal finishes, and spacious living areas. Private outdoor space perfect for relaxing. Conveniently located just minutes from Walt Disney World and within close proximity to Sunset Walk for dining, shopping, and entertainment. Situated in Margaritaville Resort Orlando, a highly sought-after vacation destination with strong rental demand. Ideal as a primary residence, second home, or investment property. Seller will credit buyer 6 months of HOA Fees at closing! HOA & The Fins Up Club covers Cable, Internet, Trash, Landscaping, resort shuttle, theme park shuttle, resort pool and Gym. This property also includes a Home Warranty that covers all appliances, HVAC, plumbing, and electrical.

Listing is courtesy of: LIST-A-HOUSE REALTY, LLC (954-292-4012)

Listing Agent: Andrea Mark (954-644-2575)

Remarks: Short Sale. Welcome to your own slice of paradise in Margaritaville Resort Orlando! This unfurnished residence offers the perfect opportunity for a primary home, long-term rental, or investment property. Located just a 5-minute walk to shops, restaurants, grocery stores, and entertainment, convenience is at your doorstep. The home features an open layout with plenty of natural light and a relaxed, tropical feel throughout. Offered at a competitive price, this unit is ready for your personal touches—create your dream retreat in one of Central Florida’s most desirable communities. Enjoy the laid-back lifestyle Margaritaville is known for, with access to resort-style amenities and a location just minutes from Walt Disney World, I-4, and major attractions. Don’t miss this opportunity to invest in a flexible, well-located property where every day feels like a vacation.

Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)

Listing Agent: Troy Funk (941-241-3850)

Remarks: Under contract-accepting backup offers. GORGEOUS FULLY FURNISHED VILLA AVAILABLE FOR SALE AT MARGARITAVILLE RESORT ORLANDO! This Home Features 3 Bed, 3 Baths With 2 Walk in Closets! Kitchen with Quartz Countertops, Island with Seating, Stainless Steel Appliances, Washer and Dryer and Abundant Natural Light, Each of the Three Bedrooms has Ceiling Fans. One Bathroom has a Shower/Tub Combo. The Door from the Kitchen Leads you to a Beautiful Patio, Lounge Chairs and Tropical Landscaping, Palm Trees, and Tropical Foliage. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Great Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Turnkey 4BR/3BA townhome in Margaritaville Resort Orlando! Fully furnished and thoughtfully designed with an open-concept layout, modern coastal finishes, and spacious living areas. Private outdoor space perfect for relaxing. Conveniently located just minutes from Walt Disney World and within close proximity to Sunset Walk for dining, shopping, and entertainment. Situated in Margaritaville Resort Orlando, a highly sought-after vacation destination with strong rental demand. Ideal as a primary residence, second home, or investment property. Seller will credit buyer 6 months of HOA Fees at closing! HOA & The Fins Up Club covers Cable, Internet, Trash, Landscaping, resort shuttle, theme park shuttle, resort pool and Gym. This property also includes a Home Warranty that covers all appliances, HVAC, plumbing, and electrical.

Listing is courtesy of: LIST-A-HOUSE REALTY, LLC (954-292-4012)

Listing Agent: Andrea Mark (954-644-2575)

Remarks: Under contract-accepting backup offers. Short Sale. Enjoy resort living in this 4-bedroom, 3-bath townhome in the heart of Margaritaville. The open layout brings the living, dining, and kitchen together for easy hosting. The first floor includes a bedroom and full bath with a large walk-in shower and quartz vanity. Upstairs, the primary suite offers a walk-in closet and a spacious bathroom with dual sinks and a walk-in shower. Two more bedrooms and an additional full bath provide room for family or guests. Relax on your private patio with views of the tropical landscaping and a short walk to the community pool. Margaritaville offers three pools, a hot tub, fitness center, spa, dining, live entertainment, and complimentary shuttles. The location gives you quick access to theme parks, golf, dining, shopping, and major highways. Ideal as a primary home or investment. Furniture is available. Book your tour today.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Rodrigo Marsal (407-431-8503)

Remarks: GORGEOUS VILLA with WATER VIEW in Margaritaville Resort Orlando. This AMAZING Two-Floor Home features an Open Concept Living and Dining Room with Ceiling Fan, "WOOD" Tile Floors, an Island Kitchen with QUARTZ Countertop, Stainless Steel Appliances, Washer and Dryer and Abundant Natural Light, Each of the Three Bedrooms has Ceiling Fans. One Bathroom has a Shower/Tub Combo. The Door from the Kitchen Leads you to a Beautiful Patio with Lounge Chairs and Tropical Landscaping, Palm Trees and Tropical Foliage with a Serene Water Views. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price Includes Furniture/Housewares. Also Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Welcome to Paradise! This Beautifully Furnished WATERFRONT VILLA in Margaritaville Resort has 3 Bedrooms, 3 Baths, High-End Quartz Countertops, Upgraded "Wood" Tile Flooring and Appliances. Kitchen has Island with Seating, Stainless Steel Appliances, Large Counter Space and Windows with Lots of Natural Light. Master Bedroom Located Upstairs has En Suite Bathroom. Each Bedroom has Ceiling Fans and One Bathroom Includes a Shower/Tub Combo. Backyard has a Beautiful Paved Patio with Tropical Foliage! High Capacity Washer and Dryer. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES Furniture/Housewares with Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: GORGEOUS VILLA in Margaritaville Resort Orlando. This AMAZING Two-Floor Home features an Open Concept Living and Dining Room with Ceiling Fan, "WOOD" Tile Floors, an Island Kitchen with QUARTZ Countertop, Stainless Steel Appliances, Washer and Dryer and Abundant Natural Light, Each of the Three Bedrooms has Ceiling Fans. One Bathroom has a Shower/Tub Combo. The Door from the Kitchen Leads you to a Beautiful Patio with Lounge Chairs and Tropical Landscaping, Palm Trees and Tropical Foliage. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price Includes Furniture/Housewares. Also Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Welcome to paradise at 2916 On The Rocks Pt, a stunning, turnkey-ready 3-bedroom, 3-bathroom townhome located in the highly coveted Margaritaville Resort Orlando. Sold fully furnished and beautifully decorated, this property features a bright, open-concept living area that seamlessly transitions to your own private patio space—perfect for soaking in the warm Florida sunshine. Best of all, you are just steps away from one of the pristine community pools. Designed for effortless ownership, this property is an exceptional opportunity for vacation home buyers seeking a personal tropical getaway or savvy investors looking to capitalize on a premier short-term rental destination. Living in Margaritaville Resort means enjoying a world-class, island-inspired lifestyle with access to incredible amenities, including expansive lagoon-style swimming pools, the relaxing St. Somewhere Spa, a state-of-the-art fitness center, and the thrilling Island H2O Water Park. The property is also exceptionally close to the Promenade at Sunset Walk, a bustling hub packed with premier dining, retail shopping, and live entertainment. Located just minutes away from Walt Disney World Resort and other top Central Florida attractions, this townhome offers the ultimate blend of resort relaxation and theme park adventure.

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: Welcome to your ultimate getaway at 3049 Caribbean Soul Drive! This fully furnished, professionally decorated 4-bedroom, 3-bathroom townhome is the epitome of island living. As an end unit, you'll enjoy extra privacy and an abundance of natural light. Step outside and take in the serene water views, or simply walk a few steps to one of the community's beautiful pools. This property is perfect as a vacation home or an investment property, with its vibrant, Key West-style architecture and turnkey setup, complete with all the furniture, art, and decor you need to start enjoying the laid-back lifestyle immediately. Situated within the Margaritaville Orlando Resort, this townhome offers a lifestyle of luxury and convenience. Residents and guests have access to an impressive array of amenities, including multiple resort-style pools with a lazy river and water slide, the St. Somewhere Spa, a 24-hour fitness center, and a variety of on-site restaurants and bars like Euphoria Fish House and the Salty Rim Bar & Grill. The resort also features the Promenade at Sunset Walk, a vibrant destination for shopping, dining, and entertainment, and provides a complimentary shuttle service to Walt Disney World theme parks. This prime location places you close to Central Florida's world-famous attractions, premier dining, and top-tier shopping, making it a perfect retreat for both relaxation and adventure.

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: Short Sale. SPECTACULARLY FURNISHED VILLA AVAILABLE FOR SALE AT MARGARITAVILLE RESORT ORLANDO! This Home Features 4 Bedrooms and 3 Baths with a King Bed in the Primary Bedroom, a Queen Bed in Bedroom 2, a King Bed in Bedroom 3, Two Twin Beds in Bedroom 4 and a Sofa Bed in the Living Room. The Kitchen Offers Quartz Countertops, an Island with Seating, Stainless Steel Appliances, a Washer and Dryer and Abundant Natural Light. Each Bedroom has Ceiling Fans and One Bathroom Includes a Shower/Tub Combo. The Door from the Kitchen Leads to a Beautiful Patio with Lounge Chairs Surrounded by Tropical Landscaping, Palm Trees and Lush Foliage. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Great Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Welcome to Paradise. Margaritaville Orlando 3 Bedroom 3 Bath Villa Turnkey Ready for your Personal Vacation Home or Short Term Rental investment property. The Villa showcases an MRO approved City Furniture/Housewares Package ($35K Included), ceiling fans, upgraded appliances, sleek QUARTZ countertops, and beautiful 'wood 'ceramic tile flooring. A high-capacity washer and dryer conveniently located on the second floor. Resort features multiple pools, a state-of-the-art gym, H2O on-site water park, Sunset Walk Restaurants, bars, live music, retail, and more! Terrific location just minutes from DISNEY with free shuttle to the Disney, Universal and Sea World Parks. Furniture/Housewares Package included in list price. Don't Delay !

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Brian Webber (407-399-1408)

Remarks: AMAZING FULLY FURNSIHED VILLA AVAILABLE FOR SALE AT MARGARITAVILLE RESORT ORLANDO! This CORNER VILLA has 4 Bedrooms and 3 Baths, High-End Quartz Countertops, Upgraded "Wood" Tile Flooring and Appliances. Kitchen has Island with Seating, Large Counter Space and Windows with Lots of Natural Light. Master Bedroom Located Upstairs has En Suite Bathroom. Each of the Bedrooms has Ceiling Fans. Backyard has a Beautiful Paved Patio with Tropical Foliage! High Capacity Washer and Dryer. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Includes Furniture, Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Great Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Own a Slice of Paradise in Margaritaville Resort! Welcome to this move-in-ready, fully furnished 3-bedroom, 3-bathroom villa, nestled in the heart of the world-famous Margaritaville Orlando Resort. Whether you’re seeking a luxurious second home, a high-performing short-term rental, or both, this tropical oasis is a dream come true. Step Inside Paradise: This beautifully designed Key West-style villa features three spacious en-suite bedrooms, an open-concept living and dining area, and stylish finishes throughout. Large sliding glass doors lead to your private paved patio, perfect for morning coffee or evening cocktails. The bright, light-filled interior boasts 10-foot ceilings, 8-foot doors, wood-look tile flooring, and ceiling fans that enhance the breezy tropical feel. A modern kitchen awaits with sleek quartz countertops, a breakfast bar, and high-end Samsung stainless steel appliances, including a washer and dryer. Fully Turnkey – Just Bring Your Flip-Flops: Offered with the Margaritaville-approved furniture and housewares package, the villa comes fully stocked with everything you need to start enjoying or renting right away: furnishings, TVs, artwork, kitchen essentials, linens, and more. There's even a private owner's lockable closet for personal items and double-paned windows for energy efficiency and quiet comfort. Resort-Style Living Redefined: Live the good life with exclusive access to multiple lagoon-style pools, private cabanas, a fitness center, full-service spa, H2O water park, Fins Up Beach Club with live entertainment, and more. Just steps from your door, you’ll find top-rated dining, vibrant nightlife, and boutique shopping at Sunset Walk. And when adventure calls, you’re less than 5 miles from Disney World, Universal Studios, and other world-famous attractions. A Smart Investment Opportunity: Zoned for short-term rentals, this villa presents a high-income potential in one of Florida’s most in-demand vacation destinations. Enjoy the flexibility to use it for personal getaways while earning passive income when you’re away. With year-round tourism and strong rental demand, this property is truly an investor’s dream.

Listing is courtesy of: FORTUNE INTERNATIONAL REALTY (305-400-6393)

Listing Agent: Maggie Walas (407-701-0144)

Remarks: Welcome to Paradise. Margaritaville Orlando 3 Bedroom 3 Bath Villa Turnkey Ready for your Personal Vacation Home or Short Term Rental investment property. The Villa showcases an MRO approved City Furniture/Housewares Package ($35K included), ceiling fans, upgraded appliances, sleek QUARTZ countertops, and beautiful 'wood 'ceramic tile flooring. A high-capacity washer and dryer conveniently located on the second floor. Resort features multiple pools, a state-of-the-art gym, H2O on-site water park, Sunset Walk Restaurants, bars, live music, retail, and more! Terrific location just minutes from DISNEY with free shuttle to the Disney, Universal and Sea World Parks. Furniture/Housewares Package included in list price. Don't Delay !

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Brian Webber (407-399-1408)

Remarks: **Charming 2-Bedroom Townhouse with Versatile Loft in The Margaritaville Community**.Step into this brand-new, fully furnished, upgraded 2-bedroom, 2.5-bath townhouse, featuring an upstairs bonus room area that can easily serve as a third bedroom. Perfectly positioned within the desirable Margaritaville Community, this property is currently operating as a successful Airbnb, with continuous bookings that provide an exceptional investment opportunity. Annual ROI details are available upon request. Designed for comfort and relaxation, this home offers a spacious open-concept living and dining area, a modern full kitchen, and spa-style bathrooms that make every day feel like a vacation. Enjoy your morning coffee/evening cocktail from your private outdoor terrace, surrounded by lush tropical scenery.

Listing is courtesy of: REALTY ONE GROUP MAGIC CITY (407-589-9080)

Listing Agent: Nydia Pino (954-804-4971)

Remarks: This fully FURNISHED 3 bedroom townhome in Margaritaville Resort Orlando offers one of the best opportunities to own in a DISNEY area resort that allows SHORT TERM RENTALS. Whether you are looking for a vacation home, an income producing investment, or a place to enjoy Orlando year round, this property checks every box. Located just minutes from Walt Disney World, Margaritaville Resort is one of the MOST SOUGHT AFTER VACATION COMMUNITIES in Central Florida. Owners benefit from high demand for short term rentals, professional property management options, and a RESORT LIFESTYLE that attracts guests year round.This home is completely turnkey and furnished, allowing the new owner to start renting immediately without the time and expense of furnishing or designing the property. Simply close and begin generating income or enjoying the home. One of the biggest advantages of this property is its PROXIMITY to Sunset Walk, just about a 5 minute walk away, where you will find restaurants, shopping, live entertainment, bars, arcades, and a grocery store.This WALKABLE lifestyle is one of the main reasons guests choose to stay in Margaritaville. Owners and guests also enjoy access to resort style amenities including pools, water park access nearby, fitness center, entertainment, and the unique Margaritaville lifestyle experience that makes this community stand out from other vacation rental areas.With its prime location near Disney, strong rental potential, walkability to entertainment, and fully furnished turnkey condition, this property represents an EXCEPTIONAL OPPORTUNITY to own in one of Orlando’s most popular resort communities.

Listing is courtesy of: P4L REALTY LLC (407-845-9189)

Listing Agent: Michelle Fernandez (407-724-5033)