Photo by Lou

Pine Island vacation rentals

We found 414 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Pine Island that are perfect for your trip. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, such as a fireplace and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Pine Island

Showing deals for:Apr 3 - Apr 10

Image gallery for HEATED POOL Manatee Oasis Weeki Wachee Family Fun Pool Home

Living area
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

HEATED POOL Manatee Oasis Weeki Wachee Family Fun Pool Home

Spring Hill

8% off
Price is $320
$2,240 for 7 nights
All fees included
HEATED POOL Manatee Oasis Weeki Wachee Family Fun Pool Home

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Pine Island

Why visit Pine Island

  • Beautiful beaches: Pine Island boasts pristine beaches perfect for relaxation and family fun.
  • Outdoor activities: Enjoy a range of adventures, including island tours and water sports in scenic rivers.
  • Charming accommodations: Choose from cozy vacation homes, cottages, and modern condos for a perfect stay.
  • Family-friendly atmosphere: The village offers a welcoming vibe, ideal for creating lasting memories with loved ones.
  • Natural beauty: Experience the unique flora and fauna that define Florida's stunning landscape.

Popular types of accommodation in Pine Island

Pine Island vacation rentals offer a variety of options to suit every traveler’s needs. Whether you're looking for a private vacation home, a cozy cottage, or a modern condo, you'll find the perfect spot to unwind. With our selection of Palm vacation rentals and Island Palm vacation rentals, you can enjoy a serene getaway. Explore all that Pine Island has to offer and create lasting memories on your next adventure.

  • Houses: The top choice for visitors to Pine Island, offering spacious and comfortable accommodations for families, friends, or couples.
  • Condos: A popular option that combines convenience and amenities, perfect for those seeking a resort-like experience.
  • Cottages: A charming and cozy retreat, ideal for a peaceful getaway surrounded by nature.
  • Apartments: A practical choice for travelers looking for a home-like atmosphere with easy access to local attractions.
  • Villas: Luxurious and spacious, these rentals provide a lavish experience for those looking to indulge during their stay.**

Top attractions near Pine Island

Pine Island in Spring Hill, Hernando County, Florida, is an ideal destination for outdoor family beach vacations. Visitors can enjoy beautiful islands, pristine beaches, and scenic rivers, making it perfect for those seeking adventure and relaxation. Explore various island tours, consider the best vacation rentals with competitive prices, and discover unique activities that highlight the natural beauty of Pine Island for an unforgettable getaway.

  • Pine Island Beach Park: A beautiful beach that offers a relaxing atmosphere with soft sands and clear waters. Ideal for sunbathing, picnicking, and enjoying beach vibes just 0.3 miles from Pine Island.
  • Weeki Wachee River: This scenic river, located 6 miles away, is perfect for kayaking and exploring nature. Enjoy the lush surroundings and outdoor vibes while making unforgettable memories.
  • Weeki Wachee Springs State Park: Also 6 miles from Pine Island, this state park features thrilling water activities and breathtaking scenery, perfect for adventurous spirits and nature lovers alike.

Things to do recommended for couples

Ready for a romantic getaway in Pine Island? Explore the underwater wonders at Weeki Wachee Springs, enjoy a sunset stroll on the Bayport Park Pier, or indulge in luxury at Silverthorn Country Club. Each spot offers a unique experience perfect for couples seeking adventure and romance.

Things to do recommended for families

Families can explore Wever Recreation Park, located 15 miles from Pine Island, where they can enjoy outdoor activities in a serene environment perfect for relaxation and wellness. It's an ideal spot for picnics and family fun amidst nature.

Things to do recommended for groups

Explore the scenic Indigo Lane Trailhead for an outdoor adventure, enjoy a captivating performance at the Show Palace Dinner Theater for a night of culture and entertainment, and tee off at Cabot Citrus Farms for some fun in the sun with sports and relaxation.

*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 in Pine Island

If you're traveling with a group, family, or pets, or if you're seeking longer accommodations, be sure to use the filters that align with your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Pine Island with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Pine Island with young kids: Traveling with little ones can be quite a task. It’s important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pine Island: For many families, a trip isn't truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like food bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pine Island: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right 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 in Pine Island

Pine Island, a charming village in Hernando County, Florida, offers a delightful retreat for families seeking outdoor adventures and beach vacations. With its friendly atmosphere, you can enjoy a unique island experience while exploring nearby cities and neighborhoods. From cozy vacation homes to coastal living, Pine Island is the perfect getaway for those wanting to embrace the beauty of Florida’s nature and create lasting memories with loved ones.

  • Weeki Wachee Gardens: Located 3 miles from Pine Island, Weeki Wachee Gardens is a charming village that offers an abundance of outdoor adventures and stunning scenery. Known for its picturesque river and lush parks, this area is perfect for nature lovers and those seeking an adventurous experience. Visitors can engage in various activities like underwater sports and explore recreational areas that highlight the natural beauty of Florida. The nearby Weeki Wachee Springs State Park is a must-visit, featuring captivating mermaid shows and opportunities for kayaking and wildlife viewing.
  • Spring Hill: As the city where Pine Island is located, Spring Hill serves as a gateway to a wealth of outdoor and family-friendly activities. With its scenic parks and proximity to beautiful beaches, Spring Hill invites travelers to enjoy adventurous outings and leisurely strolls. Families can take advantage of the recreational areas, which include playgrounds and picnic spots. The nearby Weeki Wachee River is perfect for kayaking, fishing, and other water activities, offering a refreshing escape into nature.
  • Bayport: Situated 2 miles away from Pine Island, Bayport is a quaint village known for its family-oriented atmosphere and scenic landscapes. This community offers excellent opportunities for outdoor enthusiasts, with access to adventure activities and underwater sports. Visitors can enjoy the serene beauty of local parks and the nearby beach, making it an ideal spot for relaxation and recreation. The tranquil Bayport Park is perfect for picnics, while the charming waterfront provides a lovely setting for a day of exploration.

Best time to go to Pine Island

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January58.8°F (14.9°C)Light RainMostly SunnyAverageSlightly Low
February62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly Low
March65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
April71.6°F (22.0°C)Light RainMostly SunnyAverageAverage
May76.5°F (24.7°C)Light RainMostly SunnyAverageAverage
June80.4°F (26.9°C)Moderate RainMostly SunnyHighSlightly High
July81.5°F (27.5°C)Moderate RainMostly SunnyHighSlightly High
August81.9°F (27.7°C)Moderate RainMostly SunnyHighSlightly High
September79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
October73.9°F (23.3°C)Light RainMostly SunnyLowSlightly Low
November66.7°F (19.3°C)Light RainMostly SunnyLowAverage
December62.8°F (17.1°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you aiming to save money on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. By enrolling in our travel rewards program, OneKey, you can immediately access member discounts and earn as well as redeem OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is designed to help you plan your travels effortlessly, allowing you to create new trips, manage your plans, and organize your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Pine Island getaway

Learn about the unique charm of Pine Island with a stay in a private vacation home. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Pine Island

Do you want to find top things to see and do during your stay? Venture out of your cozy vacation rental and experience everything that makes Pine Island a one-of-a-kind vacation spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Silverthorn Country Club (11.4 mi / 18.3 km)
  • Cabot Citrus Farms (13.1 mi / 21 km)
  • Adventure Coast Fun Park (10.9 mi / 17.5 km)
  • The Dunes Golf Club (10.9 mi / 17.6 km)
  • Southern Woods Golf Club (13.6 mi / 21.9 km)
  • Hernando Oaks Golf and Country Club (14.3 mi / 23.1 km)

Exploring the natural features in Pine Island

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Pine Island is a great place to get out in nature. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Pine Island Beach Park (0.3 mi / 0.5 km)
  • Bayport Park Boat Ramp (2.5 mi / 4.1 km)
  • Weeki Wachee Springs State Park (6.2 mi / 10 km)
  • Weeki Wachee River (6.2 mi / 10 km)
  • Weeki Wachee Springs (6.3 mi / 10.1 km)
  • Bird Island (7.2 mi / 11.6 km)

Transportation options to and around Pine Island

Fly into Tampa Intl. Airport (TPA), the closest airport, located 41.7 mi (67 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into St. Petersburg-Clearwater Intl. Airport (PIE), which is 46.1 mi (74.2 km) away.

Frequently asked questions

What is the best area to stay in Pine Island when booking a vacation rental?
When booking a vacation rental in Pine Island, Florida, one of the best areas to consider is Bokeelia, located on the northern end of the island. Bokeelia offers a charming, laid-back atmosphere with beautiful views of the surrounding waters. This neighborhood is great for those looking to connect with nature, as it is home to the famous Pine Island Sound, which is ideal for fishing, boating, and kayaking. One of the top attractions in Bokeelia is the historic Pineland, where you can explore the Calusa Heritage Trail and learn about the area's rich Native American history. Additionally, the Bokeelia Fishing Pier provides fantastic opportunities for angling and enjoying breathtaking sunsets.

Another great option is St. James City, which is situated on the southern part of Pine Island. Known for its vibrant community and stunning waterfront properties, St. James City is a fantastic spot for those seeking a more social atmosphere. The area is popular for its proximity to the beautiful beaches of the nearby Sanibel and Captiva Islands, making it a great base for beach lovers. The Tarpon Lodge is a popular point of interest here, offering delicious dining options and stunning views of the water, making it an excellent place to unwind after a day of exploration.

Both Bokeelia and St. James City have a variety of vacation rental properties, ensuring that you'll find something to suit your needs, whether you're looking for a cozy cottage or a spacious waterfront home.
How much does it cost to rent a vacation home in Pine Island?
Prices for vacation rentals in Pine Island 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 Pine Island 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 Pine Island vacation house rentals?
You can find great discounts on house rentals in Pine Island 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.
Can I find long-stay vacation rentals in Pine Island?
A long-stay vacation rental in Pine Island 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.
Are there any Pine Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pine Island 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.
When is the best time to visit Pine Island for a vacation rental?
The best time to visit Pine Island for a vacation rental is during the peak season from June to August. This vibrant period attracts sun-seekers and nature enthusiasts eager to explore the island's beautiful beaches and natural landscapes. With temperatures typically ranging from the mid-70s to the low 90s Fahrenheit, visitors can enjoy ample opportunities for outdoor activities such as kayaking, fishing, and hiking along scenic trails.

June is particularly popular, as it marks the beginning of the summer season when families flock to the island for a memorable getaway. The warm weather complements the island's laid-back atmosphere, making it superb for beach outings, shell collecting, and leisurely strolls through the lush surroundings.

For those looking to save a bit on accommodations while still enjoying a pleasant experience, consider visiting in November. This month offers a quieter atmosphere, allowing you to savor the island's charm without the bustling crowds. You can relish the mild temperatures, typically in the low 70s, while taking advantage of fewer tourists and stunning sunsets.

Ultimately, your ideal time to visit Pine Island will hinge on whether you prefer the lively summer energy or the tranquil, budget-friendly experience found in the fall.
How early should I book a Pine Island vacation rental?
Book your Pine Island 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 Pine Island?
In Pine Island, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and laid-back lifestyle. The island is renowned for its stunning beaches, particularly in the Bokeelia and St. James City neighborhoods, where visitors can relax on the sandy shores or engage in water sports like kayaking and paddleboarding.

In Bokeelia, the nearby Pine Island Sound offers excellent fishing opportunities, and the area is dotted with charming local eateries that serve fresh seafood. The Matlacha Pass Aquatic Preserve, located between Pine Island and the mainland, is another highlight, providing a habitat for diverse wildlife and opportunities for eco-tourism.

On the other hand, St. James City is known for its tranquil atmosphere and proximity to the beautiful mangroves, making it a great spot for nature walks and birdwatching.
Can I change or cancel my Pine Island home rental booking on Vrbo?
To find Pine Island 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 cabin or a beach condo, 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 Pine Island 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas