Pinehurst vacation rentals

We found 216 vacation rentals — enter your dates for availability

Discover a selection of 44 homes and other vacation rentals in Pinehurst that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the amenities you need and want, such as WiFi and cable TV. Whatever you're looking for, you'll be able to choose a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Pinehurst

Showing deals for:Dec 5 - Dec 12

Image gallery for Villa with swimming pool & spa - Poolside Grill, Family-friendly, Water-view

Swimming pool and spa
9.2 out of 10 rating
Wonderful
(14 reviews)

Villa with swimming pool & spa - Poolside Grill, Family-friendly, Water-view

Rotonda West, FL

6% off
Price is $418
$2,926 for 7 nights
All fees included
Villa with swimming pool & spa - Poolside Grill, Family-friendly, Water-view

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Find out more about Pinehurst

Find out more about Pinehurst

Why visit Pinehurst

  • Outdoor Activities: Enjoy a variety of outdoor adventures, from beautiful beaches to urban parks and nearby national parks.
  • Family-Friendly Experiences: Engage in activities suitable for all ages, making it a perfect destination for families.
  • Charming Neighborhoods: Explore welcoming communities with picturesque homes, enhancing your vacation experience.
  • Diverse Accommodations: Choose from a range of vacation rentals, including cozy homes, condos, and villas to suit your needs.
  • Friendly Atmosphere: Experience the warm hospitality of locals who make Pinehurst a delightful getaway.

Popular types of accommodation around Pinehurst

Planning a getaway to Pinehurst? You’ll find a variety of popular vacation rentals, including private homes, condos, and villas that cater to every traveler's needs. Whether you're searching for cozy three-bedroom homes or accommodations with fitness centers, Pinehurst has something for everyone. Connect with friendly hosts who are ready to make your stay memorable. Start your adventure in beautiful Pinehurst, Lakeland, FL, and experience the perfect blend of comfort and convenience.

  • Houses: The top choice for travelers in Pinehurst, offering spacious and comfortable accommodations perfect for families and groups.
  • Condos: A popular option for those seeking modern amenities and a convenient location, ideal for couples and small families.
  • Villas: These upscale properties provide a luxurious experience with private pools and beautiful surroundings.
  • Apartments: A practical choice for solo travelers and couples, offering the comforts of home in a compact space.
  • Cottages: Quaint and charming, these cozy retreats are perfect for a peaceful getaway in nature.**

Top attractions near Pinehurst

Pinehurst, Rotonda West, Florida, is perfect for outdoor enthusiasts and families seeking a beach getaway. Visitors can enjoy a variety of attractions, including beautiful beaches, urban parks, and nearby national and state parks. With activities catering to all ages, Pinehurst offers a delightful blend of relaxation and adventure, ensuring that everyone can have a memorable experience during their vacation.

  • Englewood Beach: A stunning stretch of white sand, Englewood Beach offers a laid-back atmosphere perfect for sunbathing, swimming, and beachcombing. Enjoy picturesque sunsets and the soothing sound of waves, making it an ideal spot for relaxation and beach vibes.
  • Don Pedro Island Beach: Accessible via boat, this remote beach is part of a state park and boasts breathtaking scenery. Ideal for adventure seekers, you can explore nature trails, spot wildlife, and enjoy outdoor activities in a serene environment.
  • Gasparilla Marina: A hub for outdoor enthusiasts, Gasparilla Marina features boat rentals and fishing opportunities. Enjoy beach vibes while indulging in water sports or simply soaking in the coastal atmosphere.

Things to do recommended for couples

For a romantic getaway in Pinehurst, visit the Oyster Creek Golf Club, just 2 miles away. Enjoy the luxurious atmosphere while playing a round of golf or relaxing in the beautiful surroundings. It's the perfect spot to create special memories together.

Things to do recommended for families

During your family vacation in Pinehurst, you can catch a game at Charlotte Sports Park, unwind at Cedar Point Environmental Park, and enjoy activities at the Englewood Recreation Center, all offering fun and relaxation just a short drive away.

Things to do recommended for groups

Your group can enjoy a delightful day at Fishermen's Village, a vibrant shopping center 13 miles from Pinehurst. For sports enthusiasts, the Riverwood Golf and Country Club, located 7 miles away, offers great outdoor activities. Don’t miss the Lemon Bay Playhouse, a charming theater just 6 miles from Pinehurst.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, your family, or pets, or if you're planning an extended stay, be sure to set your filters according to your priorities. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Pinehurst with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Pinehurst with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pinehurst: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pinehurst: If you're in search of vacation rentals with discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Pinehurst

Pinehurst, nestled in Rotonda West, Florida, offers a delightful blend of outdoor activities and family-friendly experiences. Explore the surrounding neighborhoods, where you can find charming homes and welcoming communities. Just minutes from Pinehurst, you'll discover the perfect spots for relaxation and recreation, making it an ideal destination for sports enthusiasts and families alike. Enjoy the warm atmosphere and friendly locals that make Pinehurst a wonderful vacation getaway.

  • Rotonda West: Located in the heart of Florida's Gulf Coast, Rotonda West is a scenic city that offers an enchanting blend of outdoor and recreational experiences. Surrounded by lush greenery and beautiful waterways, this community is a haven for golf enthusiasts, featuring several well-maintained golf courses. Families can enjoy the tranquil beaches and parks, making it an ideal spot for relaxation and outdoor activities. Visitors can explore nearby family-friendly beaches and islands, adding to the charm of this vibrant area.
  • Pebble Beach: Just 0.8 miles from Pinehurst, Pebble Beach is a delightful neighborhood that invites visitors to indulge in outdoor adventures. Known for its beautiful beaches and urban parks, it’s a perfect destination for families looking to enjoy a day in the sun. Golf courses dot the landscape, providing opportunities for both leisurely play and serious competition. The area also features an arcade adventure zone, ensuring fun for all ages. With its welcoming atmosphere, Pebble Beach is a great spot for family bonding and outdoor exploration.
  • Broadmoor: Also located 0.8 miles from Pinehurst, Broadmoor is a charming neighborhood that offers a similar allure as its neighbor. It combines the excitement of outdoor activities with the relaxation of beach life. Families can enjoy the local golf courses and the arcade adventure zone, while beautiful urban parks provide perfect picnic spots. The nearby beaches offer a chance to soak up the sun and enjoy water activities. Broadmoor’s friendly vibe and scenic surroundings make it a fantastic place for a family getaway.

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 HighSlightly Low
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 SunnyAverageAverage
December67.3°F (19.6°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can change significantly. Moreover, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash on the total booking amount. Being the trip organizer certainly has its perks. Become a member of our One Key rewards program to enjoy exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient place for you to plan new trips, manage your ongoing travel arrangements, and review your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Pinehurst?
In Pinehurst, vacation houses are the most popular type of vacation rental, with around 42 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor spaces for relaxation. Additionally, there are several villas and cottages that offer a charming alternative, typically set in quieter neighborhoods and providing a cozy atmosphere for travelers.
Are there any beach house rentals in Pinehurst?
In Pinehurst, Florida, there are approximately 86 beach house rentals available, primarily situated in neighborhoods that offer convenient access to local beaches and recreational areas. These vacation homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor patios or decks great for enjoying the warm Florida weather. Many properties also include amenities such as private pools, BBQ grills, and easy access to nearby parks and nature trails, making them ideal for families or groups looking to relax and explore the area's natural beauty.
How much does it cost to rent a vacation home in Pinehurst?
Prices for vacation 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 vacation 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.
What are popular rental amenities in Pinehurst?
In Pinehurst, popular rental amenities include private pools, kitchens, and patios, which enhance the overall experience for travelers. Many vacation rentals feature heated pools, offering a comfortable swimming experience regardless of the season. The presence of a kitchen allows guests to prepare their meals, making it convenient for families or those looking to enjoy home-cooked dishes.
Are there any family house rentals in Pinehurst?
In Pinehurst, Florida, there are numerous family-friendly house rentals available, with around 42 options to choose from. This charming area is known for its welcoming atmosphere and proximity to various attractions that cater to families. Many of these properties offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play safely.

Visitors will appreciate the amenities often found in these homes, such as air conditioning, Wi-Fi, and laundry facilities. The neighborhood provides easy access to nearby parks, golf courses, and recreational areas, making it an excellent choice for those looking to blend relaxation with outdoor activities.
Can I rent a vacation home with a pool or hot tub in Pinehurst?
In Pinehurst, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 48 options for properties with pools and 10 with hot tubs. This charming area is known for its beautiful landscapes and golf courses, making it a desirable spot for relaxation and recreation.

Travelers can expect a range of amenities in these rentals, including private pools, hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens for preparing meals. Many properties may also offer additional features such as outdoor dining spaces, fire pits, and game rooms, enhancing the overall vacation experience.
Are there any Pinehurst vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pinehurst with parking available—perfect for families or travelers 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.
Are there pet-friendly vacation rentals in Pinehurst?
Yes, you can book pet-friendly vacation rentals in Pinehurst, Florida. The area offers a range of vacation rentals that welcome pets, providing a convenient and enjoyable stay for travelers with furry companions. Many of these rentals come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

Pinehurst is known for its proximity to beautiful parks and recreational areas, making it a great choice for pet owners. Nearby, you'll find parks that feature walking trails and open spaces, superb for taking your dog for a stroll. The area's community vibe and pet-friendly atmosphere enhance the experience, allowing you to enjoy your vacation while ensuring your pets feel at home.
Can I find long-stay vacation rentals in Pinehurst?
A long-stay vacation rental in Pinehurst is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Pinehurst for a vacation rental?
The best time to visit Pinehurst for a vacation rental is during the peak season from February to April, with March standing out as the most popular month. This period attracts travelers seeking a warm escape and offers a superb blend of outdoor activities and local events, making it ideal for those who appreciate quality experiences.

During these months, the climate is pleasantly mild, with temperatures typically ranging from the low 50s to mid-70s Fahrenheit. This comfortable weather invites visitors to explore the beautiful landscapes and enjoy outdoor activities such as golfing, hiking, and scenic walks through the charming streets of Pinehurst.

If you're looking for a more budget-friendly option, consider visiting in October. This month provides a wonderful opportunity to enjoy the area's tranquil ambiance, with fewer crowds and a chance to appreciate the natural beauty of the fall season without the hustle and bustle of peak tourist traffic.

Ultimately, your choice of when to visit Pinehurst should reflect your preferences for vibrant activities and community events or a quieter retreat filled with autumn colors.
Are there any remote work vacation rentals in Pinehurst?
In Pinehurst, Florida, travelers seeking remote work vacation rentals will find a variety of options available, with around 47 properties suiting this need. Many rentals are equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desk spaces, and comfortable office chairs. Some properties even offer additional features like laptop workspaces and computer monitors, ensuring a productive environment for those working while traveling.

The area boasts a charming suburban atmosphere, with easy access to local parks and recreational areas, superb for taking breaks during the workday. Additionally, Pinehurst is conveniently located near the vibrant communities of Clearwater and St. Petersburg, where you can find a range of dining, shopping, and entertainment options. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Pinehurst vacation rental?
Book your Pinehurst vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pinehurst?
In Pinehurst, Florida, visitors can explore several attractions that highlight the area's natural beauty and recreational opportunities. The nearby Lake Tarpon offers a variety of water activities, including boating and fishing, making it a popular spot for outdoor enthusiasts. The scenic parks, such as John Chestnut Sr. Park, provide walking and biking trails, picnic areas, and opportunities for birdwatching.

For golf lovers, Pinehurst is close to several golf courses that cater to different skill levels, providing a great way to enjoy the lush landscapes. Additionally, the nearby Gulf Coast beaches, like those in Tarpon Springs and Clearwater, are easily accessible and offer beautiful sandy shores for sunbathing and swimming.
Can I change or cancel my Pinehurst home rental booking on Vrbo?
To find Pinehurst vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy 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 vacation 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.

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