Side by Side Orlando Villas and Vacation Rentals

We often get asked if we have any Orlando villas that are side by side / next to each other or opposite so I have put together a list which will help you. This would be ideal for two families or groups of friends that want to be close to each other during there holiday but still have there own space for some quite downtime next to the pool.

You will still need to check the availability of the Orlando villas with each of the owners, but if you book far enough in advance you should be able to get all of them together.

We have a number of side by side or opposite Orlando vacation villas on Windsor Hills, Hampton Lakes, Calabria, Cypress Pointe and Cumbrian Lakes. We have lots more as well so please check back as I update this list.

Windsor Hills Resort Side by Side Rentals

We have over 20 Windsor Hills Orlando villas to rent. Windsor Hills 403 & 405 are side by side villas so you have a total of 8 bedrooms and 8 en-suite bathrooms so ideal for two families.

Windsor Hills Resort ID 403 - 4 Bed 4 Bath (all en-suites)

Windsor Hills ID 405 - 4 Bedroom 4 Bath Vacation Rental

Windsor Hills Resort Side by Side

Hampton Lakes Side by Side Villas

Hampton Lakes 1589 & 571 are two houses about (68 yards) so you have a total of 10 bedrooms and 4 en-suite bathrooms (sleep up to 20 people).

Hampton Lakes ID 1589 - 5 Bedroom 3 Bath with Lake View

Hampton Lakes ID 571 - 5 Bedroom 3 Bath with Lake View

Hampton Lakes 1440 & 110 are almost opposite each other (39 yards) and give you a total of 8 bedrooms and 6 bathroom with 4 en-suites (sleep up to 16 guests).

Hampton Lakes Villa ID 1440 - 4 Bedroom 3 Bath

Hampton Lakes 4 Bedroom 3 Bath Villa ID 110

The Shire at West Haven Side by Side Villas

We now have over 30 Orlando villas on The Shire at West Haven. We have created a blog post showing all the side by side villas on the The Shire at West Haven rather than listing them all here.

The Shire at West Haven Side By Side Villas


We have a selection of Calabria vacation rentals in Orlando just minutes from Disney.

Cumbrian Lakes Side by Side Orlando Villas

We have 7 Cumbrian Lakes Florida villas all on the same street within a few minutes for each other. We have listed 5 of them below which are the closest but the other two are also less than a minute apart. Cumbrian Lakes villa ID 5310 and ID 5645 are two doors apart (63 yards) and give you 9 bedrooms and 6 baths.

Cumbrian Lakes villa ID 5310 - 5 Bedroom 3 ½ Bath vacation rental with Lake View

Cumbrian Lakes villa ID 5645 - 4 Bedroom 3 Bath with Lake View

Cumbrian Lakes villa ID 5498 is only a couple of doors away from ID 5645 (59 yards). It has 4 bedrooms and 3 bath with a lake view.

Cumbrian Lakes vacation rental ID 5498 - 4 Bedroom 3 Bath

Cumbrian Lakes Florida Villas ID 61 and 383 are next-door to each other and offer 11 bedrooms and 7 bathrooms. Both homes have lake views and games rooms.

Cumbrian Lakes Villa ID 61 - 6 Bedroom 4½ Bath Rental

Cumbrian Lakes Villa ID 383 - 4 Bedroom 3 Bath Vacation Rental

Cypress Pointe

Cypress Pointe villas - All of the Orlando villas we have on Cypress Pointe are less than a minutes walk from each other as it's a very small community. The main section is a loop which is where all of the villas we have are located.

We currently have over Cypress Pointe villas available. We have already created a specific blog post just showing the Cypress Pointe side by side villas.

Highlands Reserve Side By Side Villas

If you are looking for side by side vacation rentals on Highlands Reserve please check out our other blog posts.

We will be adding more side by side or opposite Orlando vacation villas to this list very shortly so check back again soon.

Comments (8) -

  • Hi
    I am interested in 2 villas, side by side or with in walking distance, eg same community. I would like to pay no more then £1200 per villa, I am wondering can you help me in finding 2 4 bedroom villas.  are dates are from 13th Sepetmeber 2019   to    27th September 2019. It is for 2 families or 5 .
    Regards Kristie

    • Hi Kristie, thanks for your comment, we have lots of side by side Orlando villas on the following communities. The Retreat at Champions Gate, Solterra Resort, Storey Lake, Highlands Reserve. It's best to contact the owners as most with know which other villas are next door or close by. We will also be adding more blog posts shortly showing the side by side vacation rentals on Champions Gate, Solterra Resort and Storey Lake.
  • Hi there, my friends and I are looking at renting 2 houses side by side in orlando near Disney from December 27, 2018 to January 3, 2019.  

    In total there is 14 of us.

    Do you have any availability?  If so, what are your prices.
  • Looking for two homes that will accommodate my family and I.  We need homes from June 21st to June 24th.  
    • Hi Lakrishia, thanks for your comment, please go to our home page and enter your dates and size of home and do a search. Then you just contact the owners direct to get a quote and book, very easy.
  • Can you help me. I am looking four, 5 bedroom villas in a row or very close together. Where do I begin? Having a big reunion and would like homes. Close to each other for evenings by the bbq and pool. Thank you in advance.
  • Looking for side by side villas to accommodate 38 people total. Near disney world.  July17-24
  • I am looking for two places side by side or close to each other preferably in the Retreat at Champions resort. One family will be arriving July 2-18- 6 adults and 4 kids. The second family will be arriving July 10-18, 2 adults and 4 kids. We can divide up for second week so would need 5 bedrooms definitely for first week and 4 bedrooms for second week.

    Thank you

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