Orlando Airbnb alternatives included these side by side villas in Bears Den Reunion Resort in Orlando

Side-by-side villas and vacation rentals

Book side-by-side homes in top destinations , including great options in Orlando resorts, all with luxury amenities and free concierge services.

Location

Orlando

Side-by-side Villa Rentals

Whether you need multiple side-by-side villas on the same street, or require a high volume of vacation rentals in the 100s, Top Villas with its portfolio of 10000+ resort homes is the #1 solution, for all your accommodation needs. Our award-winning villas promote exclusive home comfort and a bespoke level of service, with the convenience of side-by-side accommodation in world-class resorts and destinations. When priced per person per night, they also offer an undeniably cost-effective alternative to costly hotel room blocks.

Indeed, the exceptional quality and versatility of our resort homes make them ideal for accommodating large family reunions, multigenerational groups, sports' teams, VIP guests and their entourages, year-round conference stays, wedding groups, Jewish Passover, golf groups and more. With our largest 5-star Reunion Resort offering 300+ villas, you can be sure your group will enjoy the carefree experience of staying in the same exclusive, gated community - with access to the same first-class facilities and optional Concierge Services.

Explore our villas online or reach out to our dedicated and knowledgeable Group Sales team, for a seamless side-by-side villas booking service.

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Concierge Services for Side-by-side homes

Our tailor-made Concierge Services offer the perfect way to elevate your multiple villa stay. From the start to finish of your villa rental experience, we have everything covered - from private jet charters, airport transfers, car hire and group shuttles to grocery shops, conference equipment, private chefs and babysitting. We're also here to arrange your golf tee times, spa treatments, private excursions, villa kashering, party planning, yacht charters and more. Explore our optional services today and take the fuss out of your large group booking, with Top Villas.

Cheerleader sports team staying at side by side villas in Orlando

Side-by-side Villas for Sport's Teams

Heading to a sports tournament? Our side-by-side resort homes near the major arenas and training grounds are perfect for accommodating large sports' groups.

That's because our award-winning collection of side-by-side villas set the scene for an epic place to stay and play. Equipped with private gyms, spas, pools with jacuzzis and even basketball courts and golf simulators, our sports' team vacation homes are set in private, 5-star resort communities with world-class facilities - for a high octane base from which players, coaches and groups can relax, entertain and train. Enhance your experience further, with our bespoke sports' team Concierge Services.

Located a short distance from the main venues and training centers, American football teams, cheerleading squads, basketball teams, professional golf players, soccer players, tennis players and more will find our side-by-side villas a cut above the competition.

Bears Den 18 aerial view golf side by side villas

Side-by-side Golf Villas

From the championship golf resorts in Florida and California to Arizona and the Caribbean, our side-by-side villas promise the ultimate golfing trip. In the sun-drenched golfer's paradise of Orlando, golfing groups can easily reach the fairways, thanks to our beautiful villas in Orlando's premier golf resorts. Our most exclusive side-by-side golf villas can be found within Reunion Resort - the home of 3 signature golf courses and the Golfzon Leadbetter Academy. Within Reunion Resort, a selection of our golf villas and condo rentals offer scenic views across the fairways - take our exclusive Bear's Den community, which overlooks the clubhouse and 18th hole of the Nicklaus course. We also have a fantastic selection of side-by-side golf villas in Champions Gate, Providence and Highlands Reserve. Many of our side-by-side golf villas are also equipped for multigenerational family groups, ensuring the whole gang can stay and enjoy the scenery and experience an upscale resort vacation.

Those seeking a sun-drenched Caribbean golfing trip can enjoy unforgettable rounds of play in some of the #1 golf courses, with our superb collection of side-by-side villas located in prestigious golf resorts, such as Royal Westmoreland in Barbados and the renowned Casa de Campo resort in the Dominican Republic.

Complemented by our optional Concierge Services, golfing groups can easily tailor-make their trip with transport, private chefs, housekeeping, golf tee times, buggy rentals, PGA-certified golf lessons and more. Let us help you source your perfect side-by-side golf villas and contact our experienced Group Sales team - for a golfing trip that runs as smoothly as the fairways.

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With over 100,000 happy guests every year, you can book your next stay with us with total confidence.

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View of plane landing in Miami for conference stays

Side-by-side Corporate Rentals

Our exclusive corporate-friendly villas are ideal for accommodating conference stays in the US. Whether you require a villa to impress delegates, a mansion to accommodate C-level executives or multiple side-by-side villas and condos to accommodate your team, Top Villas is here to provide a seamless experience.

Think our homes are just for families? Think again! Corporate groups in need of the perfect accommodations can easily select must-have amenities, as well as deselect themed bedrooms, when searching for available homes on our site. Using the Map tool on each Resort listing results page also makes it a breeze to find side-by-side villa locations within a resort. Our experienced Corporate Sales team are also on hand to personally assist and advise on the most suitable side-by-side villas.

From neighboring villas and opulent mansions nearby the Orange County Convention Center in Orlando, to side-by-side rentals in San Diego and deluxe private villas in the same exclusive Miami or LA neighborhoods, you'll find our award-winning collection nothing short of exemplary.

Enhance your conference stay or corporate team-building trip further, with our personalized Concierge Services. From private jet charters, group airport transfers and venue shuttles to corporate hospitality, golf tee times, conference equipment and venue hire, Top Villas are here to ensure a successful corporate stay.

Rendering of Villatel Orlando Resort single family home

Side-by-Side Villas for Families & Groups

When looking to book multiple villas for mixed groups in the same resort or even street, our side-by-side villa options are just the thing. Offering luxury villa amenities and desirable resort locations, your large multigenerational family or group will easily be able to soak up an effortless vacation or special occasion, with on-tap resort facilities at the ready. Experience all the must-see attractions and activities nearby and embrace a hassle-free itinerary whilst away. Our most luxurious side-by-side villas are also located in resorts with beautiful wedding venues, making them ideal for accommodating large wedding groups. Not sure where to start? Our experienced Sales Team are on hand to help!

Side-by-side Family & Group Villa Rentals

Families and large groups can easily kick back and feel at home within our neighboring villa rentals. Equipped with open concept living areas, games rooms, themed kids' bedrooms and home theaters, you'll experience 5-star convenience and comfort. What's more, our opulent mansion rentals boast sprawling private pools and additional "wow-factor" amenities, such as home gyms and spas, bowling alleys, golf simulators and even bowling alleys, making them the perfect choice for those looking to impress and host lavish reunions. On-resort, soak up dining options, resort pools, sports' facilities, kids' activities and even water parks! Located within easy reach of the parks and top attractions, you can easily delve into the very best our world-class destinations have to offer.

Side-by-side Frum Villas for Jewish holidays

Our side-by-side Orlando villas are also ideal for accommodating Kosher-friendly stays and Jewish Passover programs, with many of our resorts conveniently placed for reaching nearby facilities, including fully kashered villas with access to on-resort event spaces and synagogues.

Traveling in a large group may seem daunting, but our Concierge team are here to take that worry away. Our optional Concierge Services ensure your multiple villa stay is as carefree as possible.