Oakes Estates holiday rentals
We found 68 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Oakes Estates that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, including Wi-Fi and parking. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
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Find the best place to stay - Oakes Estates

Key West Style Luxury Home with resort heated saltwater pool & infinity line spa
Sleeps 10 · 5 bedrooms · 3 bathrooms

Spacious Family Retreat with Pool Gym Sauna Pickleball and Guest Suite SLEEPS 16
Sleeps 16 · 6 bedrooms · 4+ bathrooms

Tuscan Villa ▪ Walk to Beach ▪ Heated pool & SPA ▪
Sleeps 8 · 4 bedrooms · 3 bathrooms

Rose View Cottage
Sleeps 14 · 5 bedrooms · 3 bathrooms

Cypress Woods for Seasonal or Summer Stays W Golf
Sleeps 6 · 2 bedrooms · 2 bathrooms

Lovely Private Cottage, less than 5 miles to the beach!!!
Sleeps 4 · 1 bedroom · 1 bathroom
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
When is the best time to visit Oakes Estates for a holiday rental?
January marks the most popular time to visit Oakes Estates, as it kicks off the peak season that runs through March. This period is especially appealing to travellers seeking warm weather and outdoor activities, making it a prime time for enjoying the natural beauty of Florida. With temperatures ranging from 15 to 25 degrees Celsius, visitors can comfortably partake in activities like hiking, exploring local parks, or simply relaxing by the water.The vibrant setting during these months attracts those looking to escape colder climates, providing plenty of opportunities for socialising and enjoying local events. Oakes Estates offers a tranquil setting while still being close to attractions that enhance your holiday experience.For those seeking a more budget-friendly option, visiting in October can be a great choice. This month offers a quieter charm, allowing for leisurely exploration of the area's natural landscapes and a chance to experience the local culture without the crowds. You might find that local restaurants and attractions offer promotions, adding extra value to your stay.
What are the top attractions in Oakes Estates, Florida, United States of America?
In Oakes Estates, Florida, visitors can enjoy a tranquil and picturesque environment, primarily known for its lush landscapes and residential charm. The area is close to the beautiful beaches of Naples, where attractions like the Naples Pier and the vibrant shopping scene at Third Street South can be easily accessed.Nature enthusiasts may appreciate the proximity to nearby parks such as the Corkscrew Swamp Sanctuary, which offers miles of walking trails through stunning wetlands, superb for exploring Florida's unique wildlife. The area is also not far from the Naples Botanical Garden, renowned for its diverse plant collections and serene setting.For those interested in cultural experiences, the nearby Artis—Naples hosts art exhibits and performances, adding to the region's appeal.
Are all fees included in the Oakes Estates holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oakes Estates holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakes Estates with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oakes Estates holiday homes?
You can find great discounts on holiday homes in Oakes Estates on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oakes Estates holiday home booking on Stayz?
To find Oakes Estates holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oakes Estates?
A long-stay holiday home in Oakes Estates is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oakes Estates holiday home?
Book your Oakes Estates holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oakes Estates?
Prices for holiday homes in Oakes Estates vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakes Estates to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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