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Pine Island vacation rentals

We found 393 vacation rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 7 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:Nov 7 - Nov 14

Exceptional

(14 reviews)

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

Spring Hill, FL

8% off

All fees included

Exceptional

(6 reviews)

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

Spring Hill, FL

8% off

All fees included

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

All fees included

Exceptional

(108 reviews)

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

Brooksville, FL

12% off

All fees included

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

8% off

All fees included

Out back on canal with new deck and floating dock.

Exceptional

(31 reviews)

EPIC Weeki Wachee riverfront home Waterfront Kayaks included

Spring Hill, FL

8% off

All fees included

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

All fees included

Exceptional

(9 reviews)

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

Spring Hill, FL

8% off

All fees included

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 BEACH HOUSE w/ BEACH. 5+ SPOTLESS! SLEEPS 6. 2022 RATES! QUIET.

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

Premier Host

Quiet summer getaway

Peace of mind
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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

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:

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 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 most popular type of vacation rental accommodation in Pine Island?

According to our research, cottages are considered the most popular vacation property type in Pine Island. But as you know, everyone's idea of an epic trip is bound to be different. Vrbo has vacation homes with every size, shape and budget in mind, so you're bound to find the perfect fit.

How much does it cost to rent a vacation rental in Pine Island?

Property type, length of stay and time of year are some of the conditions that can influence the price of a vacation home. Simply add your dates of travel to find your dream escape. From cozy cabins to sprawling villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in Pine Island?

Prices for beach houses in Pine Island differ depending on the type and size of the property and time of year you're traveling. All you have to do is enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use the filters to narrow down your search by ratings, nearby activities and more.

Are there pet-friendly vacation rentals in Pine Island?

Yes, there are. You'll have your pick of six vacation homes that roll out the welcome mat in Pine Island on Vrbo. Our cuddly best friends deserve a break too, so simply use our search function for pet-friendly vacation rentals to book a property where your puppy can lap up the good times.

What are popular rental amenities in Pine Island?

When it comes to rental amenities that people look for in Pine Island, an ocean view, a barbecue grill and a nearby waterfront are the most popular. With Vrbo vacation homes, you'll have options to fit your taste and style, whether you're taking a trip with your partner, your family or even pets.

Are there large group vacation rentals in Pine Island?

Take your pick of six Vrbo properties in Pine Island that can host five or more guests. You'll get all the room and privacy you need to chill out with the people you're vacationing with — and no one else.

Are there vacation rentals in Pine Island that welcome kids?

Gather your whole crew for a fun-packed adventure in Pine Island at one of our six family-friendly vacation properties. Lots of these stays provide amenities that are perfect for getaways with children, such as laundries, living rooms and pools. Simply check the "Properties good for families" filter box and choose your favorite.

Can I find two-bedroom vacation rentals in Pine Island?

Pine Island has four two-bedroom vacation properties to choose from. Go for a vacation home with all the space and privacy you need at a price you'll love on Vrbo.

Are there vacation rentals with WiFi in Pine Island?

Pick from two vacation rentals with WiFi in Pine Island. If you want to disconnect from daily life during your escape, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Pine Island?

Select your travel dates and then use the filters to search for vacation rentals with air conditioning in Pine Island on Vrbo. With six air-conditioned properties on offer here, you can look forward to a cool and comfortable stay.

How old do you have to be to rent a vacation rental in Pine Island?

The minimum age requirements can vary across properties on Vrbo, so double-check the rules of the vacation home in Pine Island you want to book. But usually, it's 16, 18 or 21.

How long can I rent a vacation rental in Pine Island for?

The length of time you can rent a vacation rental in Pine Island is up to the property. Simply enter your desired dates to look at a list of options offering extended stays. With tons of features like air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to discover somewhere perfect to call your home away from home in Pine Island.

Does Vrbo offer discounts for vacation homes in Pine Island?

On Vrbo, you'll find fabulous discounts and deals for Pine Island. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're planning a short getaway or a much longer stay, Vrbo has options for every style and budget.