Pinehurst holiday lettings

We found 225 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

October 2025

November 2025

Discover a selection of 47 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.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Pinehurst

NEW!! SEA STAR OASIS: ROTONDA WEST 3BD/2BTH HEATED POOL HOME! 18 MIN TO BEACH!

Sleeps 6 · 3 bedrooms · 2 bathrooms

Top rated rentals - Pinehurst

Premier Host

Lovely House with Pool

We had a great stay in Rotondo West - property was in a lovely quite neighbourbood. Bed was super comfy and kitchen was well equipped. Beach tools available and was great to use around the many beaches nearby. Thank you for sharing your lovely home Julia

Jo W.

Stayed Jun 2024

Wonderful

Everything about the villa was right. Easy access. Mega helpful host. Comfortable, clean and well equipped. Well maintained. So enjoyed the pool and the waterway view at the back.

Margaret S.

Stayed Nov 2023

Premier Host

Relaxing peaceful stay

Perfect place for a get away from it all holiday in a very different part of Florida to what most people see. The villa has everything you need and more and the lack of immediate neighbours give it a very private and peaceful feeling unlike the villas in central Florida. The BBQ is a great ‘extra’. The nearby beaches at Englewood, Boca Grande and Stump Pass are stunning and Venice and Naples are lovely places to visit. The pace of life seems so much slower and relaxing but the bikes and golf clubs are there if you need something a little more energetic. The solar pool heating was enough to keep the pool a nice temperature. The villa is very well equipped with lots of little extras that make it feel really like home. We loved playing Monopoly after so many years. If there was a downside it was the villas remoteness from shops and well known restaurants although Farlows on the Water was great. You need a car!! However this is America and you need a car in most places you stay if you want to get a real feel for the location. In summary 5* if you want peace quiet privacy and to see a different side of Florida. Mark was a pleasure to deal with and made our whole vacation experience one to remember. Thank you for letting us stay in your lovely villa.

William (Bill) B.

Stayed Sept 2019

Great property, really enjoyed our stay.

Had a great time in a great location. IKea theme appreciated. Clean and modern,

Chris W.

Stayed Apr 2019

Find out more about Pinehurst

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	63.7°F (17.6°C)	No Rain (Dry)	Mostly Sunny	Moderately High	Average
February	66.0°F (18.9°C)	No Rain (Dry)	Sunny	Moderately High	Average
March	68.7°F (20.4°C)	No Rain (Dry)	Sunny	Moderately High	Slightly High
April	73.9°F (23.3°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	78.1°F (25.6°C)	Light Rain	Mostly Sunny	Average	Average
June	82.0°F (27.8°C)	Light Rain	Mostly Sunny	Average	Average
July	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
August	83.7°F (28.7°C)	Light Rain	Mostly Sunny	Moderately Low	Average
September	81.9°F (27.7°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
October	77.5°F (25.3°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
November	71.2°F (21.8°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly Low
December	67.3°F (19.6°C)	No Rain (Dry)	Mostly Sunny	Average	Average

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

What is the most popular type of holiday rental in Pinehurst?

In Pinehurst, holiday houses are the most prevalent rental option, with around 40 available throughout the area. These properties typically come with multiple bedrooms, spacious living areas, and fully equipped kitchens, making them superb for families or groups looking for a comfortable home base. Many holiday houses also feature outdoor patios or gardens where guests can relax and enjoy the pleasant Florida weather. Additionally, there are several villas and cottages that offer a more intimate setting, often with unique designs and amenities such as private pools or access to local golf courses.

Are there any beach house rentals in Pinehurst?

In Pinehurst, Florida, there are approximately 43 beach house rentals available, suiting a variety of preferences. These properties are typically situated near popular points of interest, such as the scenic coastline and local parks, allowing guests to enjoy the natural beauty of the area. Most beach houses come equipped with essential amenities, including fully equipped kitchens, spacious living areas, and outdoor spaces where guests can relax and take in the fresh air. Many rentals also offer features like private pools, BBQ facilities, and easy beach access, making them ideal for families or groups seeking a memorable getaway.

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?

March is the most popular time to visit Pinehurst, Florida, as the weather is pleasantly warm and ideal for enjoying outdoor activities. During this peak season, which spans from February to April, visitors flock to the area to experience its vibrant golf culture and engage in various recreational pursuits, such as hiking and cycling through the beautiful landscapes.

Throughout March, temperatures typically hover in the mid to high 20s Celsius, providing a comfortable climate for exploring the charming local parks and waterfront areas. This is also a fantastic time to indulge in some birdwatching or simply relax by the serene lakes that Pinehurst is known for.

If you're looking for a more budget-friendly option, consider visiting in October. The fall season brings a unique charm to Pinehurst, with fewer crowds and the opportunity to enjoy milder temperatures while still engaging in outdoor activities like golf or leisurely strolls through the scenic surroundings.

Are there any remote work holiday rentals in Pinehurst?

In Pinehurst, Florida, there are numerous holiday rentals suitable for remote work, with around 47 options available. Travellers can expect to find properties equipped with essential amenities that cater to remote work needs, such as reliable Wi-Fi, dedicated desk spaces, and comfortable office setups. Many rentals also include features like laptop workspaces and ergonomic desk chairs to ensure a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

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.

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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

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.

More holiday ideas

Holiday rentals

Sign in to contact hosts and keep track of all your messages