Pine Island holiday rentals

We found 452 holiday rentals — enter your dates for availability
Discover a selection of 9 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:13 Nov - 20 Nov

Pool
Welcome!
Lobby
Interior
Exceptional
(115 reviews)

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

Brooksville

16% off
AU$3,188
for 7 nights, 1 home
AU$455 per night
includes taxes & fees
Paradise found! Private heated pool spa . 3700 sq ft of luxury on 2+ acres!
Peace and quiet
Swimming pool looking to the southwest
Spacious lanai
The kitchen
Exceptional
(50 reviews)

An American Dream

Spring Hill

7% off
AU$2,420
for 7 nights, 1 villa
AU$346 per night
includes taxes & fees
An American Dream
Pool
Dining
Outdoor dining
Living area
Exceptional
(57 reviews)

Private Cabana home. Heated pool. 3400 sq ft of luxury! Kids and pets welcome.

Spring Hill

16% off
AU$3,188
for 7 nights, 1 home
AU$455 per night
includes taxes & fees
Private Cabana home. Heated pool. 3400 sq ft of luxury! Kids and pets welcome.
Exterior
Pool
Property grounds
Living area
Exceptional
(28 reviews)

River home with huge arcade, hot tub, kayaks, mini golf course, 80in TV

Spring Hill

8% off
AU$6,003
for 7 nights, 1 home
AU$858 per night
includes taxes & fees
River home with huge arcade, hot tub, kayaks, mini golf course, 80in TV
Peace and quiet
View from the lanai
Spring time
Well equiped kitchen
Exceptional
(8 reviews)

An American Dream

Spring Hill

7% off
AU$2,399
for 7 nights, 1 villa
AU$343 per night
includes taxes & fees
An American Dream
Room
Private kitchen
Living area
Interior
Wonderful
(9 reviews)

Charming 4-bedroom house with WiFi and AC in pleasant Spring Hill

Brooksville

7% off
AU$2,337
for 7 nights, 1 home
AU$334 per night
includes taxes & fees
Charming 4-bedroom house with WiFi and AC in pleasant Spring Hill
Private kitchen
Exterior
Living area
Living area
Exceptional
(16 reviews)

4 Bedroom Farmhouse On The River 2

Spring Hill

8% off
AU$3,859
for 7 nights, 1 home
AU$551 per night
includes taxes & fees
4 Bedroom Farmhouse On The River 2
Dining
Pool
Living area
Interior
Wonderful
(33 reviews)

Waterfront Paradise w Manatees Fishing Kayaks in the Backyard! Newly Renovated

Spring Hill

8% off
AU$10,971
for 7 nights, 1 home
AU$1,567 per night
includes taxes & fees
Waterfront Paradise w Manatees Fishing Kayaks in the Backyard! Newly Renovated
Private kitchen
Terrace/patio
Marina
Room
Exceptional
(14 reviews)

Private Garden Shower, Arcade Games, Sups & Yaks

Spring Hill

8% off
AU$3,853
for 7 nights, 1 home
AU$550 per night
includes taxes & fees
Private Garden Shower, Arcade Games, Sups & Yaks
Dining room
Pool
Exterior
Room
Exceptional
(46 reviews)

Charming Beach Getaway Villa with Large Private heated Pool

Spring Hill

7% off
AU$2,005
for 7 nights, 1 home
AU$286 per night
includes taxes & fees
Charming Beach Getaway Villa with Large Private heated Pool
Living area
Gulf views from the gallery! Wine or coffee? Great spot to enjoy both
So much entertainment space under the home
Private kitchen
Exceptional
(87 reviews)

Steps to the beach! Minutes to WEEKI WACHEE.

Spring Hill

7% off
AU$2,346
for 7 nights, 1 home
AU$335 per night
includes taxes & fees
Steps to the beach! Minutes to WEEKI WACHEE.
Interior
Private kitchen
Living area
Living area
Exceptional
(32 reviews)

Four Beds, three baths, heated pool, and a Golf Course. What more do you need!!

Spring Hill

8% off
AU$3,461
for 7 nights, 1 home
AU$494 per night
includes taxes & fees
Four Beds, three baths, heated pool, and a Golf Course. What more do you need!!
Private kitchen
Beach
Nice an Quiet
Exterior detail
Exceptional
(8 reviews)

Florida escape Quiet area.Restaurants all over,Clearwater 1 hr away,Orlando1hr.

Spring Hill

5% off
AU$3,030
for 7 nights, 1 home
AU$433 per night
includes taxes & fees
Florida escape Quiet area.Restaurants all over,Clearwater 1 hr away,Orlando1hr.
Private kitchen
Dining
Private kitchen
Interior
Exceptional
(18 reviews)

4BR Waterfront • Dock + Boat Slip • Direct Gulf

Spring Hill

7% off
AU$2,566
for 7 nights, 1 home
AU$367 per night
includes taxes & fees
4BR Waterfront • Dock + Boat Slip • Direct Gulf
Exterior
Private kitchen
Living area
Dining
Exceptional
(20 reviews)

Beautiful Custom Home - only 3 Minutes to Weeki Wachee Springs & Hospital

Spring Hill

7% off
AU$2,130
for 7 nights, 1 home
AU$304 per night
includes taxes & fees
Beautiful Custom Home - only 3 Minutes to Weeki Wachee Springs & Hospital
Private kitchen
Property grounds
Property grounds
Interior
Exceptional
(20 reviews)

Peaceful house right on the spring. Great place to get away from everything.

Spring Hill

7% off
AU$2,566
for 7 nights, 1 home
AU$367 per night
includes taxes & fees
Peaceful house right on the spring. Great place to get away from everything.
Opposite Side Of Second Bedroom. TV & Kids Toys In Basket! New "Stone" Floor!
Our newly renovated fish cleaning station- 8/15. Bar Sink & Cutting Board for U
From Sliding Glass Door Through The Kitchen- Automatic Trashcan On Right Of Pic!
Living Room Angle Facing 40" HDTV. Notice the Lovely New Carpet! Nice & Cozy!!!!
Exceptional
(137 reviews)

The Manatee Hideaway-3Bed-2Bath-2Deck-50'Dock-6Kayak& Canoe-Adventure Awaits You

Spring Hill

6% off
AU$1,647
for 7 nights, 1 home
AU$235 per night
includes taxes & fees
The Manatee Hideaway-3Bed-2Bath-2Deck-50'Dock-6Kayak& Canoe-Adventure Awaits You
There is a step to get into the sunroom
Property grounds
Step to bedrooms
Private kitchen
Exceptional
(62 reviews)

Newly Remodeled Weeki Wachee River Retreat

Spring Hill

8% off
AU$2,633
for 7 nights, 1 home
AU$376 per night
includes taxes & fees
Newly Remodeled Weeki Wachee River Retreat
Interior
Interior
Property grounds
Private kitchen
Exceptional
(14 reviews)

The Perfect Gateway Home with a large pool area, Gazebo, all fenced in.

Spring Hill

8% off
AU$2,740
for 7 nights, 1 home
AU$391 per night
includes taxes & fees
The Perfect Gateway Home with a large pool area, Gazebo, all fenced in.
View of dock from screened gazebo. The screen panels are pulled back in photo.🌅
View showing the steps from dock to kayak ramp, the chairs & ladder on dock. 🪜
Kitchen with double sink in island. 🏝️
Another living room wall mural view. 🌅
Exceptional
(52 reviews)

The Manatee Hideaway II-3 Bed/2Bath-40' Dock-5 Kayaks&Canoe-Adventure Awaits You

Spring Hill

6% off
AU$1,647
for 7 nights, 1 home
AU$235 per night
includes taxes & fees
The Manatee Hideaway II-3 Bed/2Bath-40' Dock-5 Kayaks&Canoe-Adventure Awaits You
Living area
Pool
Exterior
Private kitchen
Exceptional
(45 reviews)

Direct Gulf Access Home w/ Floating Dock and Pool

Spring Hill

8% off
AU$2,906
for 7 nights, 1 home
AU$415 per night
includes taxes & fees
Direct Gulf Access Home w/ Floating Dock and Pool
Interior
Interior
Interior
Private kitchen
Exceptional
(6 reviews)

Relaxing Studio Just Minutes from Weeki Wachee Springs

Spring Hill

8% off
AU$921
for 7 nights, 1 apartment
AU$132 per night
includes taxes & fees
Relaxing Studio Just Minutes from Weeki Wachee Springs
Dining
Directly on the main river. Just down from Rogers Park!
Private kitchen
Private kitchen
Exceptional
(260 reviews)

DIRECT WEEKI WACHEE RIVERFRONT!! KEY WEST PARADISE!

Spring Hill

8% off
AU$4,544
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
DIRECT WEEKI WACHEE RIVERFRONT!! KEY WEST PARADISE!
Living area
Dining
Property grounds
Private kitchen
Exceptional
(105 reviews)

Waterfront w access to the Weeki Wachee River & Gulf of Mexico - Dog Friendly!

Spring Hill

7% off
AU$2,273
for 7 nights, 1 home
AU$325 per night
includes taxes & fees
Waterfront w access to the Weeki Wachee River & Gulf of Mexico - Dog Friendly!
  • 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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:

  • Silverthorn Country Club (11.4 mi / 18.3 km)
  • Cabot Citrus Farms (13.1 mi / 21 km)
  • The Dunes Golf Club (10.9 mi / 17.6 km)
  • Hernando Oaks Golf and Country Club (14.3 mi / 23.1 km)
  • High Point Golf Club (8.2 mi / 13.2 km)
  • Adventure Coast Fun Park (10.9 mi / 17.5 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 most popular type of holiday home accommodation in Pine Island?
Based on our data, houses are the most in-demand type of property in Pine Island. But that goes without saying, everyone's idea of the perfect stay is bound to be different. Stayz has holiday homes with every size, shape and budget in mind, so you're sure to find your ideal fit.
How much does it cost to rent a holiday home in Pine Island?
The average price for a holiday home in Pine Island is based on several factors, such as property type, length of stay and season. Whether you're dreaming about a sprawling villa with lots of space or a cosy cottage perfect for just you and the kids, just add your travel dates to discover stays with unbeatable value.
How much does it cost to rent a beach house in Pine Island?
The average price for a holiday home near the beach in Pine Island will depend on when you're going and the type and size of property you want. You can easily and quickly find prices on Stayz by entering your dates of travel. Then use our handy filter tool to select the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Pine Island?
Pack a suitcase and a bone for your pup because Pine Island has six holiday homes that put out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and dates, then check the "Pets allowed" filter box.
What are popular home amenities in Pine Island?
The most popular home amenities people are searching for in Pine Island include nearby museums, a barbecue grill and an electric car charging station. Whether you're on the road with buddies, family or even pets, Stayz holiday homes include the best amenities for ultimate relaxation with the people you love.
Are there large group holiday homes in Pine Island?
Yes, there are six holiday properties in Pine Island that can accommodate five or more guests. From family trips to special occasions like birthday parties, these stays have enough space to gather with the people you love.
Are there holiday homes in Pine Island that welcome kids?
Gather your entire family for a memorable adventure in Pine Island at one of our six family-friendly holiday properties. A lot of these stays offer amenities that are perfect for getaways with children, such as laundries, multiple bedrooms and pools. Just click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Pine Island?
There are plenty of exciting things to see and do with the family in Pine Island, such as:
  • Pine Island Beach Park
  • Weeki Wachee Springs
  • Weeki Wachee Springs State Park
Can I find two-bedroom holiday homes in Pine Island?
Gather your family and enjoy peace, privacy and comfort in one of the four two-bedroom holiday homes Pine Island has to offer.
Are there holiday homes with WiFi in Pine Island?
Pine Island has two holiday homes with WiFi, so you can stay connected while you're on holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to writing and sending emails, these Stayz homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Pine Island?
Pine Island has six holiday homes where you'll be able to chill out in air-conditioned comfort. To book a property on Stayz with this perk, enter your preferred travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Pine Island?
The minimum age is normally 16, 18 or 21. It can differ across properties on Stayz, so check the rules of your preferred Pine Island holiday home before you book.
How long can I rent a holiday home in Pine Island for?
The amount of time you can stay in a Pine Island holiday home for is up to each property. Just tap in your travel dates to browse available options that offer long-term stays. They come with everything you need to make your extended getaway more comfortable and convenient, such as kitchens and laundries. Some holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.