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Oak Island, Kissimmee, Florida, United States of America

Oak Island holiday lettings

We found 19,658 holiday rentals — enter your dates for availability

Discover a selection of more than 10,000 holiday rentals in Oak Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 101 per night, and villas and houses are popular options for a stay in Oak Island. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Oak Island

Upscale Disney World Retreat 4 Mi to Resort Gates!

Sleeps 10 · 4 Bedrooms · 3 Bathrooms
£ 202 avg/night
(13)

Updated, modern 4BR/3BR private pool TH steps to clubhouse, 5 miles to WDW.

Sleeps 8 · 4 Bedrooms · 3 Bathrooms
£ 131 avg/night
(24)

Clean! Private Pool! Comforts of home just minutes away from Disney!!

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
£ 128 avg/night
(32)

Disney Rental Home with Private Heated Pool, Minutes from Major Attractions

Sleeps 9 · 3 Bedrooms · 2 Bathrooms
£ 101 avg/night
(56)

Magical Mickey Home ★Gated Resort ★Private Pool ★Clean ★Contactless ★Near Disney

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
£ 110 avg/night
(45)

***NEWLY RENOVATED 2020*** Private Pool - Gated Resort - Near DISNEY

Sleeps 10 · 4 Bedrooms · 3 Bathrooms
£ 172 avg/night
(50)

Search 19,658 holiday rentals

Top rated rentals — Oak Island
Stayed Apr 2021

Cozy home

We enjoyed our week's stay in this wonderful home! The townhome was easy to find, clean, and cozy. The location is great and the private pool was perfect for our little family. Communication was good with the owner and the maintenance staff she sent ...

Valerie s.
Valerie s.
Stayed Mar 2021

Afordable great place to stay

This property was so nice, clean, comfortable and amazing with the private pool. I looked at a lot of properties similar to this and most were much more expensive. We didn't have any issues at the property, it was quiet and a great location. The owne...

Jenifer D.
Jenifer D.

Noblesville, IN

Stayed Mar 2021

Perfect for our stay

Spent 3 nights here while visiting Disney and Universal. Location was perfect. The home was spacious and clean- beds were comfy and had all the amenities we needed. We even used the community pool for a quick swim before we headed back home and it wa...

Denise M.
Denise M.
Stayed Mar 2021

Wonderful experience.

Wonderful experience. House is clean, very nice and in a safe peaceful community. Private pool was perfect for our Florida “Staycation”. Lots of shopping and restaurants nearby and a short drive to Disney and Universal. Property owner/manager is very...

Jennifer S.
Jennifer S.
Stayed Mar 2021

Spectacular!

This property was amazing! Looks just like the pictures. We had family ranging from newborn to 76 and everyone was accommodated. My kids loved the pool! Manuel is the best when it comes to communication! Great customer service. This home was truly ou...

Angela W.
Angela W.
Stayed Mar 2021

Well Maintained Property

We really enjoyed our stay at Natalie’s place. She was always very responsive and was even nice enough to set up the heat for the pool when we requested it close to our arrival date. The property is very well maintained and it is a spacious townhome....

Eileen T.
Eileen T.
Stayed Feb 2021

Great property

Property was clean, spacious and just as described. Very close to Disney and all the attractions that we were in town for. Although we didn't end up cooking it was nice that the kitchen was fully stocked and even had various seasonings if needed. The...

Crystal G.
Crystal G.
Stayed Feb 2021

Winter get away

We thoroughly enjoyed our stay at this property! The villa was decorated very nice and was nice and clean. It was so nice having linens on the beds and towels for your use, especially for those of us who flew in. Although wash clothes would have been...

Tammy M.
Tammy M.
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Can I find a vacation rental around Oak Island?

Yes, our 2021 property listings offer a large selection of 19,658 vacation rentals near Oak Island. From 4,906 villas to 15,710 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oak Island for a holiday or a weekend are on Vrbo.