Photo by Lou

Pine Island holiday lettings

We found 389 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

August 2025

September 2025

Discover a selection of 7 homes and other holiday rentals in Pine Island that are perfect for your trip. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a pool and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Pine Island

Showing deals for:14 Nov - 21 Nov

Exceptional

(14 reviews)

Direct Gulf access 4-bedroom estate with a private boat dock

Spring Hill, FL

7% off

£279 per night

includes taxes & fees

Exceptional

(6 reviews)

Charming 3-bedroom home, Springhill, heated pool, , 3bdrms 2bath, daybed sleep 8

Spring Hill, FL

8% off

£203 per night

includes taxes & fees

Out back on canal with new deck and floating dock.

Exceptional

(31 reviews)

EPIC Weeki Wachee riverfront home Waterfront Kayaks included

Spring Hill, FL

7% off

£275 per night

includes taxes & fees

Exceptional

(108 reviews)

Paradise found! Private heated pool spa . 3700 sq ft of luxury on 2+ acres!

Brooksville, FL

11% off

£271 per night

includes taxes & fees

Outdoor 8 foot pool
Heating optional
View of waterway

Exceptional

(7 reviews)

Spacious Waterfront with heated swimming pool. 5-bedroom home in Hernando Beach

Spring Hill, FL

8% off

£750 per night

includes taxes & fees

Dock with ladder, kayak launch, picnic table, yoga dec, fire pit, movie theater

Exceptional

(14 reviews)

Waterfront, king bed, movie theater, kayaks, float mat, yoga, screened lanai

Spring Hill, FL

7% off

£311 per night

includes taxes & fees

Heated Pool, with a beautiful view of the gulf

Exceptional

(10 reviews)

Spacious 4BR Waterfront Home w/ Heated Pool, Dock & Gulf Access, Sleeps 14+

Spring Hill, FL

8% off

£487 per night

includes taxes & fees

Exceptional

(9 reviews)

Beautiful 3 BR Home|Saltwater Pool|Fenced Yard|8 Min to Weeki Wachee River

Spring Hill, FL

14% off

£144 per night

includes taxes & fees

On the Golf Course! Pool and Lanai with view of the Golf Course.

Exceptional

(27 reviews)

Beautiful 4 BR-2.5 Bath-Office-Golf Course-Pool-Hot Tub-Sleeps 9-Dog Friendly!

Spring Hill, FL

9% off

£192 per night

includes taxes & fees

Exceptional

(10 reviews)

5 Bedrooms - Spacious - 7 Kayaks - Firepit - 2 mins to Rogers Park - KING beds

Spring Hill, FL

8% off

£407 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Pine Island

WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA

Sleeps 6 · 2 bedrooms · 1 bathroom

Pine Island Beach House. 3481 Harbor Dr. Spring Hill (Weeki Wachee) FL 34607.

3/2 FL GULFSIDE BCH-HOUSE & 2 BEACHES! 10-EXCEPTIONAL. SPOTLESS! SLEEPS 6. Ahh!

Sleeps 6 · 3 bedrooms · 2 bathrooms

Pine island - Weeki Wachee Ocean View Home- Walk to Beach on secluded island

Sleeps 8 · 3 bedrooms · 4 bathrooms

Location, Location, Location! You've Found It!

Coastal Cozy Cabana | Steps to Beach • Kayaks • Big Yard • Peaceful Escape

Sleeps 10 · 3 bedrooms · 2 bathrooms

Ocean Front House, GulfViews, Sunset, Dolphins, Pine Island, Tampa, Orlando

Sleeps 6 · 3 bedrooms · 1 bathroom

Top rated rentals - Pine Island

Manatees in the Weeki Wachee River! What an unforgettable experience :)

Premier Host

Rustic house in great location

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, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find out more about Pine Island

Why visit Pine Island

Stunning natural scenery: Pine Island boasts breathtaking landscapes, including serene beaches and winding rivers, perfect for nature lovers.
Family-friendly beach activities: Enjoy relaxing days at Pine Island Beach Park, ideal for families seeking outdoor fun.
Variety of accommodations: Choose from charming cottages, private vacation homes, and modern condos to suit your preferences.
Outdoor adventures: Engage in exciting excursions that allow you to explore the beautiful surroundings and partake in various activities.
Welcoming atmosphere: Experience a friendly and relaxed environment that makes for an enjoyable holiday.

Popular types of accommodation in Pine Island

If you’re planning a getaway to Pine Island, the excitement begins with selecting the perfect accommodation. The most sought-after options include houses, quaint cottages, and modern condos. Whether you prefer a beach house with stunning views, beach chairs for leisurely sunbathing, or barbecue grills for evening gatherings, Pine Island has something to suit every traveller's needs. Discover your ideal vacation rental and make unforgettable memories on this beautiful island.

Houses: The top choice for visitors to Pine Island, offering spacious and comfortable living, ideal for families or groups.
Condos: A popular option that combines convenience and amenities, perfect for those seeking a modern retreat.
Cottages: These charming dwellings provide a quaint and cosy atmosphere, perfect for a romantic getaway.
Apartments: An excellent choice for self-catering, offering flexibility and a homely feel during your stay.
Villas: Luxurious and spacious accommodations, ideal for those looking for an upscale experience.**

Top attractions near Pine Island

Pine Island in Spring Hill, Hernando County, Florida, is an ideal destination for families seeking outdoor beach holidays. Visitors can enjoy the stunning scenery and explore various points of interest, including beautiful islands, serene beaches, and winding rivers. Whether you're travelling with family or friends, Pine Island offers a plethora of activities and experiences for those who appreciate nature and outdoor adventures.

Pine Island Beach Park: A delightful beach located 186m from Pine Island, offering a relaxing atmosphere with sandy shores and tranquil waters, ideal for sunbathing and picnicking.
Weeki Wachee River: Situated 3.7km away, this picturesque river boasts stunning scenery and outdoor activities, perfect for kayaking, canoeing, and enjoying nature's beauty.
Weeki Wachee Springs State Park: Also 3.7km from Pine Island, this state park provides thrilling adventures, outdoor exploration, and captivating scenery, featuring the famous mermaid shows and river rides.

Things to do recommended for couples

For a romantic getaway in Pine Island, explore the enchanting Weeki Wachee Springs for underwater adventures, indulge in luxury at Silverthorn Country Club, or enjoy an evening of entertainment at Colorama Music. Each offers a unique experience perfect for couples seeking memorable moments together.

Things to do recommended for families

Families can unwind at Wever Recreation Park, a delightful recreational area located 9.3km from Pine Island. With its emphasis on wellness and relaxation, it's the perfect spot for a family day out, offering opportunities for picnics, nature walks, and enjoying the great outdoors together.

Things to do recommended for groups

Discover the Indigo Lane Trailhead for a thrilling outdoor adventure, challenge your mates at The Dunes Golf Club, or enjoy a delightful evening at the Show Palace Dinner Theater, where entertainment and culture come alive. Perfect for group bonding in Pine Island!

What do I need to keep in mind when booking a vacation in 'Pine Island

If you're travelling with a group, family, pets, or planning for an extended stay, be sure to tailor your search with the appropriate priorities. Here are some helpful booking tips for using Vrbo.

Traveling to Pine Island with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for socialising with a group. Thankfully, you can easily refine your search for these options and many others on Vrbo.
Traveling to Pine Island with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
Taking your pets with you to Pine Island: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If you can relate to this, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Pine Island: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include additional preferences in your search, such as a parking space, a well-equipped kitchen, or even a private pool.

Where to stay near Pine Island

Embarking on a holiday to Pine Island, Spring Hill, offers a delightful escape into nature. This charming village is perfect for family beach vacations, where you can unwind at Pine Island Beach Park or embark on exciting excursions. The surrounding areas in Southwest Florida boast a friendly atmosphere, ideal for both relaxation and adventure. Whether you're looking for a tranquil getaway or budget-friendly options, Pine Island provides a welcoming experience for all travellers.

Spring Hill: Located 5.6km from Pine Island, Spring Hill is a vibrant city that beckons outdoor enthusiasts and families alike. Known for its stunning scenery, visitors can enjoy a plethora of activities including adventure sports and underwater exploration. The area boasts beautiful parks, picturesque rivers, and inviting beaches, making it an ideal spot for leisurely strolls and picnics. Whether you're kayaking on the river or enjoying a family day out at the local recreational areas, Spring Hill offers a delightful blend of relaxation and adventure.
Bayport: Situated a mere 1.2km from Pine Island, Bayport is a quaint village famed for its outdoor charm and family-friendly atmosphere. This delightful locale is perfect for those seeking adventure, with numerous opportunities for underwater sports and recreational activities. The nearby rivers, parks, and beaches provide a scenic backdrop for a day spent enjoying nature’s beauty. Visitors can immerse themselves in the tranquillity of the area while engaging in various outdoor pursuits that the village has to offer.
Weeki Wachee Gardens: Just 1.9km from Pine Island, Weeki Wachee Gardens is a picturesque village renowned for its natural beauty and adventurous spirit. This charming area invites visitors to explore its stunning landscapes while indulging in a variety of outdoor activities, including adventure sports and underwater experiences. With a national state park nearby, Weeki Wachee Gardens offers a perfect blend of relaxation and exploration, making it a must-visit destination for nature lovers and families seeking adventure.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	58.8°F (14.9°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	62.6°F (17.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	65.8°F (18.8°C)	Light Rain	Mostly Sunny	Average	Average
April	71.6°F (22.0°C)	Light Rain	Mostly Sunny	Average	Average
May	76.5°F (24.7°C)	Light Rain	Mostly Sunny	Average	Average
June	80.4°F (26.9°C)	Moderate Rain	Mostly Sunny	High	Slightly High
July	81.5°F (27.5°C)	Moderate Rain	Mostly Sunny	High	Slightly High
August	81.9°F (27.7°C)	Moderate Rain	Mostly Sunny	High	Slightly High
September	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
October	73.9°F (23.3°C)	Light Rain	Mostly Sunny	Low	Slightly Low
November	66.7°F (19.3°C)	Light Rain	Mostly Sunny	Low	Average
December	62.8°F (17.1°C)	Light Rain	Mostly Sunny	Low	Average

Booking with Vrbo is simple

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of accommodation.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient area for you to plan new adventures, keep track of your arrangements, or manage your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Pine Island getaway

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

Activities and attractions in and around Pine Island

Are you looking for attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that makes Pine Island a fun spot to go on holiday. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

Cabot Citrus Farms (13.1 mi / 21 km)
Adventure Coast Fun Park (10.9 mi / 17.5 km)
Silverthorn Country Club (11.4 mi / 18.3 km)
Hernando Oaks Golf and Country Club (14.3 mi / 23.1 km)
High Point Golf Club (8.2 mi / 13.2 km)
The Dunes Golf Club (10.9 mi / 17.6 km)

Exploring the natural features in Pine Island

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Pine Island is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

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)

Transport options to and around Pine Island

Fly into Tampa, FL (TPA-Tampa Intl.), the closest airport, located 41.7 mi (67 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.), 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 holiday rental?

When considering a holiday rental in Pine Island, Florida, the Bokeelia area is an excellent choice. This charming neighbourhood is known for its laid-back atmosphere and stunning views of the water, making it a superb spot for a relaxing getaway. Bokeelia boasts a number of properties that cater to various preferences, from waterfront cottages to more secluded retreats.

One of the highlights of staying in Bokeelia is the proximity to the stunning Pine Island National Wildlife Refuge, where you can enjoy birdwatching, hiking, and the opportunity to explore the local flora and fauna. Additionally, the area is home to the famous Tarpon Lodge, which offers a delightful dining experience with views of the sunset over the water, making it a popular destination for both locals and visitors.

Another appealing neighbourhood is St. James City, which offers a more vibrant atmosphere with waterfront access and a variety of dining options. This area features a number of holiday rentals, particularly those that cater to fishing enthusiasts, as it is known for its excellent fishing spots. The nearby Matlacha Pass Aquatic Preserve is also a must-visit, superb for kayaking and observing the diverse marine life.

How much does it cost to rent a holiday home in Pine Island?

Prices for holiday 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 holiday 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 holiday rentals in Pine Island?

A long-stay holiday rental in Pine Island 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.

Are there any Pine Island holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Pine Island 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.

What are popular rental amenities in Pine Island?

In Pine Island, popular rental amenities tend to be quite varied, reflecting the area's laid-back, tropical vibe. While there might not be a specific list of amenities that stand out, travellers can generally expect properties to offer essentials such as fully equipped kitchens, outdoor spaces like patios or decks for enjoying the warm climate, and laundry facilities for convenience. Many rentals also provide access to private docks, which is ideal for those interested in boating or fishing.

When is the best time to visit Pine Island for a holiday rental?

June is the most popular time to visit Pine Island, Florida, as it marks the start of the peak season that runs through August. During these months, the island comes alive with tourists eager to enjoy the warm weather, pristine beaches, and vibrant local culture. Expect temperatures to hover around the mid-30s Celsius, superb for sunbathing, swimming, and indulging in various water sports.

Outdoor activities abound in this sunny season, with opportunities for kayaking through the mangroves, fishing in the Gulf, and spotting wildlife in the nearby nature reserves. The lively atmosphere is complemented by local festivals and events, making it an ideal time for those seeking engagement and excitement.

If you're looking for a more budget-friendly option, consider visiting in November. This month presents a wonderful opportunity to enjoy the beautiful subtropical climate with a more tranquil ambience. You can still relish outdoor activities without the summer crowds, making it a fantastic time for relaxing beach walks or exploring the unique ecosystems of the island.

How early should I book a Pine Island holiday rental?

Book your Pine Island 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 Pine Island home rental booking on Vrbo?

To find Pine Island 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 Pine Island 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.