Countryside holiday rentals

We found 13 holiday rentals — enter your dates for availability
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What are the best holiday rentals near Countryside?
The best holiday rentals near Countryside in Naples, Florida are primarily found within the Countryside area itself and surrounding districts. You will find a great selection of properties here, ranging from private holiday houses offering privacy and space to well-appointed condos great for a comfortable stay. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties that still offer convenient access to the area.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as private pools for refreshing dips, spacious decks or patios for outdoor living, and laundry facilities for longer stays. These homes are ideal for families or groups looking for a relaxing escape with all the comforts of home.
Are there any cheap holiday rentals near Countryside?
There are several affordable holiday rentals near Countryside, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$205 per night. You might find great deals in September and October during the off-season. These rentals often include free amenities such as WiFi, toiletries, and self-parking, so you can have a comfortable stay.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. Many private holiday houses and condos offer great value, providing a comfortable base for your visit.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Countryside?
There are over 200 pet-friendly holiday rentals near Countryside, primarily private holiday houses and condominiums, making it easy to include your furry companion in your travel plans. These properties are mainly found in Naples and surrounding areas, offering amenities such as private outdoor spaces, well-equipped kitchens, and Wi-Fi, ensuring both guests and their pets have a comfortable stay.

When searching for the best pet-friendly holiday rentals near Countryside, always confirm individual property rules regarding pet size, breed restrictions, and any additional fees.
What are the top holiday rentals with pools near Countryside?
There are over 590 holiday rentals near Countryside that include access to swimming pools, with both private and shared options available. These properties are concentrated in areas surrounding Countryside, predominantly as private holiday houses or condominiums. Many of these rentals come fully equipped with amenities such as full kitchens, Wi-Fi, and outdoor spaces, making them ideal for families or groups seeking a comfortable stay.

When selecting your ideal property, consider whether a private pool, offering seclusion, or a shared outdoor pool, often part of a community complex with additional facilities, best suits your needs. For stays during cooler periods, looking for heated or indoor pool options will enhance your experience.
What are the best family holiday rentals near Countryside?
There are over 420 family-friendly holiday homes near Countryside, offering ample space and comfort for groups of all sizes. These properties often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. With such a wide selection, you can find stays with outdoor play areas, yards, and decks where kids can play, and many include entertainment like video games and books, alongside practical amenities like highchairs and travel cribs.

When choosing the best fit for your family, focus on properties where adults and kids each have space to unwind, and look for homes with practical amenities like well-equipped kitchens to save on dining out. Staying nearby means less travel each day and more time enjoying Countryside.
Are there any luxury holiday rentals near Countryside?
There are several luxury holiday rentals near Countryside that offer modern comfort. These properties often feature amenities such as private heated pools, private chefs, spa-style bathrooms with bathrobes and designer toiletries, and scenic lake views. Guests can also find properties with golf or tennis onsite.

These homes are ideal for families or larger groups, providing high-speed WiFi and efficient air conditioning. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and comfortable stay.
How much is a holiday rental near Countryside?
Holiday rentals near Countryside offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around AU$205 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$505 per night. Upscale options can cost AU$745 or more, offering extra space, amenities, or premium locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Countryside?
When visiting Countryside, several areas offer excellent holiday rental options. Old Naples is a popular choice, providing a charming setting with easy access to beautiful beaches, upscale shopping, and fine dining. Properties here often boast a luxurious feel and are a short drive from Countryside, offering convenient access to local attractions.

Another fantastic option is North Naples, known for its family-friendly properties and proximity to extensive retail parks and recreational facilities. Rentals in this area are well-suited for guests seeking a relaxed environment with plenty of amenities close by. It's a convenient drive to Countryside.

East Naples offers a more laid-back residential experience, with many properties providing access to golf courses and nature preserves. This area is great for those who appreciate a quieter setting while still being within easy reach of Countryside and the wider Naples area.
What is the cheapest month to stay near Countryside?
The cheapest time to find holiday rentals near Countryside is typically during the late Summer to early Autumn (September to October). September is frequently the single cheapest month, often providing the best deals on homes and properties, with rates potentially lower compared to peak season. Guests can often find various savings and better deals during these months, along with greater availability of holiday rentals.
Are there any lakefront holiday rentals near Countryside
Lakefront holiday rentals near Countryside are abundant, with many properties found along the shores of local lakes such as Lake Trafford or Lake Okeechobee. These properties are a short drive from Countryside, offering convenient access to water activities such as kayaking, fishing, motorboating, or simply relaxing by the shore, with swimming and various water sports also readily available.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy lake views and unwind in peaceful surroundings.
Are there any top beachfront holiday rentals near Countryside
Beachfront holiday rentals near Countryside offer direct access to the sand, often with ocean-view balconies where guests can watch the sunrise over the Gulf of Mexico. Prime locations along the coast provide immediate access to the beach, while being within a short drive of Naples' lively dining, nightlife, and shopping areas. Quieter spots nearby offer a more relaxed environment for those seeking tranquillity.

Guests can take advantage of amenities such as beach chairs, umbrellas, and often oceanfront pools, making every day effortless. Many properties feature ocean-facing rooms and private balconies. For those staying longer or travelling in groups, multi-bedroom units with private terraces or extra living space are available.
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.
What can I expect from Stayz customer service and Stayz™ 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.
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.
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.