Island Oaks Winter Rentals & Holiday Homes

Discover winter rentals Island Oaks - We found 318 exact matches

About Island Oaks Winter Rental on Rent By Owner

Planning on a winter vacation in Island Oaks? Discover 318 places to stay in Island Oaks, for those traveling with their family, friends, in groups, or for a wedding retreat.

At Rent By Owner, we have a wide range of listings for accommodations in Island Oaks, FL that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. RBO winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Island Oaks winter accommodation starts at GB £203, and the most popular properties in Island Oaks are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, RBO will make your winter trip memorable.

Rent By Owner offers a great deal for travelers planning on renting a place in Island Oaks, to enjoy these benefits and to book your winter vacation homes, go to RBO filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Island Oaks and unlock even more amazing deals.

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Frequently Asked Questions About Island Oaks Winter Rentals

The average cost for winter rentals in Island Oaks is $272 per night. RBO has a wide list of great winter places to stay near Island Oaks that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Island Oaks to find what works for you.
As of 2025, the data from Rent By Owner shows that there are over 318 private swimming pools or indoor pools accommodations near Island Oaks along with other great amenities.