Pinehurst holiday lettings

We found 229 holiday rentals — enter your dates for availability

Discover a selection of 43 homes and other holiday rentals in Pinehurst that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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Why visit Pinehurst

  • Stunning beaches: Enjoy sun-soaked days at beautiful local beaches, perfect for relaxation and recreation.
  • Outdoor activities: Engage in a variety of outdoor adventures, including hiking, cycling, and sports facilities for all ages.
  • Charming local parks: Explore picturesque parks that provide ideal spots for leisurely strolls and family picnics.
  • Welcoming community vibe: Experience the friendly atmosphere and warm hospitality of Pinehurst's residents.
  • Diverse accommodation options: Choose from a range of delightful holiday rentals, ensuring a comfortable stay.

Popular types of accommodation around Pinehurst

Pinehurst offers an array of delightful vacation rentals to suit every traveller's needs, from private holiday homes to cosy condos and elegant villas. Whether you're seeking a home in Pinehurst, exploring the charming Pinehurst Village, or enjoying the amenities of Pinehurst Resort, you'll find the perfect spot for your getaway. Our selection ensures transparency and savings, making it easier to enjoy your stay in this picturesque destination.

  • Houses: The top choice for visitors to Pinehurst, offering spacious living for families, friends, or couples in a homely atmosphere.
  • Condos: A popular option for those seeking modern amenities and easy access to local attractions, perfect for a leisurely stay.
  • Villas: These stylish properties provide a touch of luxury, ideal for a relaxing getaway with plenty of space.
  • Apartments: A convenient choice for shorter stays, offering comfort and independence in a vibrant community.
  • Cottages: Quaint and charming, these are perfect for a peaceful retreat close to nature.**

Top attractions near Pinehurst

Pinehurst, Rotonda West, is ideal for outdoor enthusiasts and families seeking a memorable holiday. With stunning beaches, urban parks, and national state parks nearby, visitors can enjoy a multitude of activities that cater to both relaxation and adventure. Whether you're after a sun-soaked day at the beach or a leisurely stroll through a park, Pinehurst offers a diverse range of attractions just minutes away, ensuring a delightful experience for all travellers.

  • Englewood Beach: A picturesque stretch of golden sand, perfect for sunbathing and swimming. The relaxed atmosphere makes it ideal for families and those seeking a tranquil day by the sea.
  • Don Pedro Island Beach: Nestled within a state park, this beach offers adventure and stunning scenery. Explore nature trails, enjoy birdwatching, or simply relax amid the beautiful surroundings.
  • Gasparilla Marina: A vibrant hub for water enthusiasts, this marina provides opportunities for boating, fishing, and enjoying the great outdoors while soaking up the coastal charm.

Things to do recommended for couples

If you’re seeking a romantic getaway in Pinehurst, consider a round of golf at the luxurious Oyster Creek Golf Club, located a mere 1.2km away. Enjoy the serene surroundings and exquisite amenities, perfect for couples wanting to unwind and spend quality time together.

Things to do recommended for families

Your family will love visiting CoolToday Park for sports excitement, exploring the natural beauty at Cedar Point Environmental Park for relaxation, and enjoying fun activities at Englewood Recreation Center. Each venue offers unique experiences, perfect for creating lasting memories together in sunny Florida.

Things to do recommended for groups

Explore Fishermen's Village for shopping and entertainment, just 8.1km from Pinehurst. Enjoy a round of golf at Riverwood Golf and Country Club, located 4.3km away, or immerse yourself in culture at the Lemon Bay Playhouse theatre, only 3.7km from Pinehurst.

What do I need to keep in mind when booking a vacation around Pinehurst

When travelling with a group, family, pets, or seeking extended stays, it's essential to refine your search according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Pinehurst with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for socialising with your group. Luckily, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Pinehurst with young kids: Travelling with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with facilities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Pinehurst: For many families, a holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortably at home.
  • Planning for a long term stay visiting Pinehurst: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Pinehurst

Pinehurst, nestled in Rotonda West, Florida, offers a delightful blend of outdoor adventures and family-friendly activities. This charming neighbourhood is perfect for those seeking a relaxing getaway, with its welcoming atmosphere and beautiful surroundings. Explore the local parks, enjoy sports facilities, and experience the warm community vibe. Nearby, you’ll find a variety of attractions that highlight the unique lifestyle and character of Pinehurst, making it an ideal destination for your holiday.

  • Rotonda West: Located a mere 1.2km from Pinehurst, Rotonda West is a charming city known for its stunning natural beauty and outdoor activities. Visitors are drawn to this area for its picturesque beaches and scenic golf courses. The expansive recreational areas provide ample opportunity for family-friendly outings, while the nearby landmarks, including family beaches and islands, offer perfect spots to relax and soak up the sun. Golf enthusiasts will find a variety of courses to enjoy, making Rotonda West an excellent destination for both relaxation and recreation.
  • Englewood: Situated 3.7km away from Pinehurst, Englewood is a delightful city that boasts beautiful beaches and outdoor experiences. This destination is ideal for those seeking both adventure and tranquillity, with numerous recreational areas and golf courses available for exploration. The local attractions include pristine beaches and a lovely bay, making it a perfect spot for families and beach lovers alike. Englewood's vibrant atmosphere, combined with its natural beauty, makes it a must-visit for anyone looking to enjoy the Florida coastline.
  • Pebble Beach: Just 497m from Pinehurst, Pebble Beach is a delightful neighbourhood that offers a blend of outdoor fun and family-oriented activities. Known for its stunning golf courses and recreational areas, this locale is perfect for those looking to unwind amidst nature. The nearby beaches and urban parks provide excellent opportunities for leisurely family outings. Whether you're playing a round of golf or enjoying a day at the beach, Pebble Beach is sure to provide a memorable experience for all visitors.

Best time to go to Pinehurst

If you're planning a trip to Pinehurst, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January63.7°F (17.6°C)No Rain (Dry)Mostly SunnyModerately HighAverage
February66.0°F (18.9°C)No Rain (Dry)SunnyModerately HighAverage
March68.7°F (20.4°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.9°F (23.3°C)Light RainMostly SunnyAverageSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.3°F (28.5°C)Light RainMostly SunnyAverageSlightly High
August83.7°F (28.7°C)Light RainMostly SunnyModerately LowAverage
September81.9°F (27.7°C)Light RainMostly SunnyModerately LowSlightly Low
October77.5°F (25.3°C)Light RainMostly SunnyModerately LowSlightly Low
November71.2°F (21.8°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
December67.3°F (19.6°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can lead to significant savings, given that prices can fluctuate. Moreover, opting for a longer stay frequently results in even better deals. To discover the ideal Vrbo property that fits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new holidays, pick up from where you last left off, or review and arrange your travel plans. You can easily access properties you've previously saved or booked, now conveniently sorted into Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Pinehurst?
Prices for holiday rentals in Pinehurst 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pinehurst to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pinehurst holiday house rentals?
You can find great discounts on house rentals in Pinehurst on Vrbo, 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.
Are there any Pinehurst holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pinehurst 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 on Vrbo 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.
Can I find long-stay holiday rentals in Pinehurst?
A long-stay holiday rental in Pinehurst 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Pinehurst for a holiday rental?
The most popular time to visit Pinehurst is during the peak season from February to April, when travellers flock to this charming destination for its pleasant climate and outdoor activities. This period is ideal for those looking to enjoy leisurely walks, golf, and nature trails, with temperatures typically ranging from 10 to 25 degrees Celsius, superb for outdoor exploration.

March stands out as a particularly vibrant month, attracting visitors eager to take advantage of the mild weather and beautiful scenery. During this time, Pinehurst comes alive with various events and activities, allowing guests to immerse themselves in the local culture while enjoying the natural beauty of the area.

If you're seeking a more budget-friendly experience, consider visiting in October. This month offers a quieter atmosphere, with fewer crowds and a chance to enjoy the stunning autumn foliage without the hustle and bustle of peak season. The weather remains mild, making it a comfortable time for outdoor pursuits and relaxation.
How early should I book a Pinehurst holiday rental?
Book your Pinehurst holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pinehurst, Florida, United States of America?
In Pinehurst, Florida, visitors can enjoy a variety of attractions that showcase the area's natural beauty and recreational opportunities. The scenic Lake Tarpon is a major highlight, offering options for fishing, boating, and picnicking along its shores. Many holiday rentals in the vicinity provide easy access to the lake, allowing guests to take advantage of the outdoor activities available.

The Pinehurst area is also known for its beautiful golf courses, making it a popular destination for golf enthusiasts. Courses like those found at nearby clubs offer picturesque landscapes and challenging play.

For those seeking a more tranquil experience, the nearby Anclote River Park features walking trails and picnic areas, superb for a relaxing day outdoors. This park provides a lovely spot to enjoy nature and is easily reachable from local accommodations.
Can I change or cancel my Pinehurst home rental booking on Vrbo?
To find Pinehurst holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pinehurst holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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 Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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 Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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