Pine Island holiday homes

We found 459 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:18 Dec - 25 Dec

Dining area
Swimming pool looking to the southwest
Spacious lanai
The kitchen
Exceptional
(50 reviews)

An American Dream

Spring Hill

7% off
NZ$2,888
for 7 nights, 1 villa
NZ$413 per night
includes taxes & fees
An American Dream
Lobby
Welcome!
Pool
Dining
Exceptional
(116 reviews)

Paradise found! Private heated pool+ spa, 3700 sq ft. Near Cobat Citrus farms.

Brooksville

12% off
NZ$6,641
for 7 nights, 1 home
NZ$949 per night
includes taxes & fees
Paradise found! Private heated pool+ spa, 3700 sq ft. Near Cobat Citrus farms.
Property grounds
Pool
Exterior
Living area
Exceptional
(29 reviews)

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

Spring Hill

7% off
NZ$11,410
for 7 nights, 1 home
NZ$1,630 per night
includes taxes & fees
River home with huge arcade, hot tub, kayaks, mini golf course, 80in TV
Living area
Exterior
Dining
Living area
Wonderful
(17 reviews)

4 Bedroom Farmhouse On The River 2

Spring Hill

8% off
NZ$4,790
for 7 nights, 1 home
NZ$684 per night
includes taxes & fees
4 Bedroom Farmhouse On The River 2
Private kitchen
Exterior
Room
Interior
Exceptional
(19 reviews)

Weeki Wachee Paradise

Spring Hill

8% off
NZ$5,569
for 7 nights, 1 home
NZ$796 per night
includes taxes & fees
Weeki Wachee Paradise
Private kitchen
Terrace/patio
Living area
Room
Exceptional
(16 reviews)

Private Garden Shower, Arcade Games, Sups & Yaks

Spring Hill

8% off
NZ$6,671
for 7 nights, 1 home
NZ$953 per night
includes taxes & fees
Private Garden Shower, Arcade Games, Sups & Yaks
Room
Private kitchen
Living area
Interior
Wonderful
(9 reviews)

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

Brooksville

7% off
NZ$2,790
for 7 nights, 1 home
NZ$399 per night
includes taxes & fees
Charming 4-bedroom house with WiFi and AC in pleasant Spring Hill
Well equiped kitchen
View from the lanai
Spring time
Outdoor dining
Exceptional
(8 reviews)

An American Dream

Spring Hill

7% off
NZ$3,209
for 7 nights, 1 villa
NZ$458 per night
includes taxes & fees
An American Dream
Sitting out on the pavers by the firepit  Enjoy!!
Exterior
entrance into the clock, house
The Garden Entrance to our home on the weeki wachee river
Exceptional
(309 reviews)

Beautiful River Front Home-Best on the Weeki Wachee-Read OUR FIVE STARS Reviews

Spring Hill

8% off
NZ$5,700
for 7 nights, 1 home
NZ$814 per night
includes taxes & fees
Beautiful River Front Home-Best on the Weeki Wachee-Read OUR FIVE STARS Reviews
Property grounds
Steps for easy water access / Kayak Launch
Living area
Kitchen island seats four, dining table seats four
Exceptional
(7 reviews)

Weeki Wachee 3BR Private Dock, Kayak, Fish & Boat, Trailer Parking, Sleeps 6

Spring Hill

8% off
NZ$3,794
for 7 nights, 1 home
NZ$542 per night
includes taxes & fees
Weeki Wachee 3BR Private Dock, Kayak, Fish & Boat, Trailer Parking, Sleeps 6
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
NZ$3,692
for 7 nights, 1 home
NZ$527 per night
includes taxes & fees
Florida escape Quiet area.Restaurants all over,Clearwater 1 hr away,Orlando1hr.
Living area
Exterior
Private kitchen
Private kitchen
Exceptional
(16 reviews)

Waterfront Octagon Home w/ Kayaks & Paddleboard

Spring Hill

7% off
NZ$2,583
for 7 nights, 1 home
NZ$369 per night
includes taxes & fees
Waterfront Octagon Home w/ Kayaks & Paddleboard
Step to bedrooms
Property grounds
Property grounds
Private kitchen
Exceptional
(62 reviews)

Newly Remodeled Weeki Wachee River Retreat

Spring Hill

8% off
NZ$3,245
for 7 nights, 1 home
NZ$464 per night
includes taxes & fees
Newly Remodeled Weeki Wachee River Retreat
Exterior
Dining
Private kitchen
Interior
Exceptional
(18 reviews)

4BR Waterfront • Dock + Boat Slip • Direct Gulf

Spring Hill

7% off
NZ$4,163
for 7 nights, 1 home
NZ$595 per night
includes taxes & fees
4BR Waterfront • Dock + Boat Slip • Direct Gulf
Exterior
Private kitchen
Living area
Interior
Exceptional
(21 reviews)

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

Spring Hill

7% off
NZ$2,543
for 7 nights, 1 home
NZ$363 per night
includes taxes & fees
Beautiful Custom Home - only 3 Minutes to Weeki Wachee Springs & Hospital
Private kitchen
Room
Marina
Living area
Exceptional
(6 reviews)

Waterfront Beach Bungalow with Pool/ 2 Bedroom

Spring Hill

7% off
NZ$2,933
for 7 nights, 1 home
NZ$419 per night
includes taxes & fees
Waterfront Beach Bungalow with Pool/ 2 Bedroom
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
Dining Area- Table With Four Chairs and Breakfast Nook With Two Chairs & 3 Bench
Living Room Angle Facing 40" HDTV. Notice the Lovely New Carpet! Nice & Cozy!!!!
Wonderful
(138 reviews)

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

Spring Hill

6% off
NZ$2,049
for 7 nights, 1 home
NZ$293 per night
includes taxes & fees
The Manatee Hideaway-3Bed-2Bath-2Deck-50'Dock-6Kayak& Canoe-Adventure Awaits You
Another living room wall mural view. 🌅
View showing the steps from dock to kayak ramp, the chairs & ladder on dock. 🪜
View of dock from screened gazebo. The screen panels are pulled back in photo.🌅
Room
Exceptional
(57 reviews)

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

Spring Hill

6% off
NZ$2,049
for 7 nights, 1 home
NZ$293 per night
includes taxes & fees
The Manatee Hideaway II-3 Bed/2Bath-40' Dock-5 Kayaks&Canoe-Adventure Awaits You
Property grounds
Interior
Private kitchen
Interior
Exceptional
(15 reviews)

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

Spring Hill

8% off
NZ$3,316
for 7 nights, 1 home
NZ$474 per night
includes taxes & fees
The Perfect Gateway Home with a large pool area, Gazebo, all fenced in.
Huge manatee passing through our backyard
  Backyard hidden spring run & can paddle to waterside dining and weeki wachee
Games room
Relax, BBQ watch wildlife and play connect 4 on the screened in upper patio.
Exceptional
(37 reviews)

Hidden Spring-run• Swimming • elevated Views & Game Rm

Spring Hill

11% off
NZ$2,835
for 7 nights, 1 home
NZ$405 per night
includes taxes & fees
Hidden Spring-run• Swimming • elevated Views & Game Rm
Main Living Room toward Dining Room
View from the stove area
Nice view while you eat a meal.
View from the dining room table.
Exceptional
(28 reviews)

Newly Listed, Sleeps 12, On River W. Kayaks included, Boat Dock , Gulf Access

Spring Hill

12% off
NZ$8,216
for 7 nights, 1 home
NZ$1,174 per night
includes taxes & fees
Newly Listed, Sleeps 12, On River W. Kayaks included, Boat Dock , Gulf Access
Outdoor dining
Pool
Exterior
Private kitchen
Exceptional
(45 reviews)

Direct Gulf Access Home w/ Floating Dock and Pool

Spring Hill

8% off
NZ$3,572
for 7 nights, 1 home
NZ$510 per night
includes taxes & fees
Direct Gulf Access Home w/ Floating Dock and Pool
Dining
Property grounds
Private kitchen
Marina
Exceptional
(5 reviews)

The Gulf Breeze - Direct Access To Gulf

Spring Hill

15% off
NZ$4,024
for 7 nights, 1 home
NZ$575 per night
includes taxes & fees
The Gulf Breeze - Direct Access To Gulf
Exterior
Buccaneer Bay
Living area
Dining
Exceptional
(8 reviews)

Old Florida bungalow on a tranquil Gulf Island Perfect for Couples or Anglers

Spring Hill

12% off
NZ$2,616
for 7 nights, 1 apartment
NZ$374 per night
includes taxes & fees
Old Florida bungalow on a tranquil Gulf Island Perfect for Couples or Anglers
  • 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

Why visit Pine Island

  • Coastal beauty: Enjoy scenic walks along the coast and explore picturesque beaches perfect for swimming and picnicking.
  • Outdoor adventures: Engage in river activities and nature walks that showcase the natural splendour of the area.
  • Family-friendly escapes: Discover a welcoming atmosphere ideal for families seeking relaxation and adventure.
  • Charming parks: Visit serene parks offering peaceful retreats and opportunities for leisurely picnics.
  • Local culture: Experience the warmth of friendly locals and the laid-back coastal vibe unique to Pine Island.

Top attractions near Pine Island

Pine Island in Spring Hill, Hernando County, Florida, offers a delightful mix of outdoor adventures and family-friendly experiences, making it an ideal holiday destination. Visitors can enjoy scenic walks along the coast, explore picturesque beaches, and partake in river activities. The area is perfect for those seeking a blend of relaxation and adventure amidst beautiful natural surroundings, ensuring memorable moments for all travellers.

  • Weeki Wachee Springs State Park: A national state park 10km away from Pine Island, offering a blend of outdoor adventure and stunning natural scenery with a touch of Florida’s timeless charm.
  • Hudson Beach: A pristine beach 24km away, where you can soak up the sun and enjoy a laid-back coastal vibe near Pine Island.
  • Old Mill House Gallery and Printing Museum: A cultural museum 24km away, revealing Florida’s rich heritage and artistic tradition close to Pine Island.

Things to do recommended for couples

For a romantic getaway in Pine Island, enjoy a sunset kayak tour through the mangroves, or indulge in a candlelit dinner at a waterfront restaurant. Don't miss a leisurely bike ride along the scenic trails, perfect for creating cherished memories together.

Things to do recommended for families

Families can explore the natural beauty of Pine Island, enjoying local wildlife and scenic views, with a short drive to local beaches and parks for outdoor fun. Adventure, relaxation and quality family time await in this charming destination.

Things to do recommended for groups

Explore the natural beauty of Pine Island by kayaking through its mangroves or enjoy a fishing charter for a day on the water. Gather your mates for a sunset cruise and savour the local seafood at nearby restaurants for a true taste of Florida.

*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 travelling with a group, family, pets, or planning for an extended stay, it's important to refine your search based on your key preferences. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pine Island with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Pine Island with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, it's wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Pine Island: For many families, a getaway isn’t truly fulfilling without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pine Island: If you’re searching for holiday rentals with great offers 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 long-term rentals. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search.

Where to stay in Pine Island

Pine Island, nestled in Spring Hill, Hernando County, is an idyllic getaway perfect for families and adventure seekers alike. With its beautiful beaches and serene parks, visitors can enjoy outdoor activities like swimming, picnicking, and nature walks. The welcoming atmosphere and friendly locals make it a wonderful destination to relax and explore. Discover the natural beauty of Pine Island and create cherished memories with loved ones in this charming coastal village.

  • Weeki Wachee Gardens: Located a mere 5km from Pine Island, Weeki Wachee Gardens is a charming village that offers a delightful outdoor adventure experience. Known for its stunning scenery, this destination is perfect for nature enthusiasts and thrill-seekers alike. Visitors can partake in various adventure activities and underwater sports, all set against a backdrop of lush landscapes and serene rivers. The nearby parks and the national state park provide ample opportunities for hiking, picnicking, and enjoying the picturesque Florida environment.
  • Spring Hill: As the city in which Pine Island is nestled, Spring Hill is a vibrant community that caters to families and adventurers. This city is renowned for its outdoor activities and recreational areas, making it an ideal spot for those seeking a mix of relaxation and excitement. The proximity to beautiful rivers and well-maintained parks enhances the travel experience, allowing visitors to engage in various activities, including water sports and beach outings. Spring Hill truly embodies the spirit of Florida’s outdoor lifestyle.
  • Chassahowitzka Wildlife Management Area: Situated 8km away from Pine Island, the Chassahowitzka Wildlife Management Area is a natural gem that showcases Florida’s rich biodiversity. Ideal for outdoor enthusiasts, this park offers a tranquil setting for exploring wildlife and engaging in kayaking adventures. The area's scenic rivers and national state park features create a perfect backdrop for a day of exploration. Visitors can immerse themselves in the beauty of nature while enjoying recreational activities that highlight the striking water features and diverse ecosystems.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January58.8°F (14.9°C)Light RainMostly SunnyAverage
February62.6°F (17.0°C)Light RainMostly SunnyAverage
March65.8°F (18.8°C)Light RainMostly SunnyAverage
April71.6°F (22.0°C)Light RainMostly SunnyAverage
May76.5°F (24.7°C)Light RainMostly SunnyAverage
June80.4°F (26.9°C)Moderate RainMostly SunnyHigh
July81.5°F (27.5°C)Moderate RainMostly SunnyHigh
August81.9°F (27.7°C)Moderate RainMostly SunnyHigh
September79.3°F (26.3°C)Light RainMostly SunnyAverage
October73.9°F (23.3°C)Light RainMostly SunnyLow
November66.7°F (19.3°C)Light RainMostly SunnyLow
December62.8°F (17.1°C)Light RainMostly SunnyLow

Booking with Vrbo is simple

Looking to cut costs on your upcoming adventure? Being open with your travel dates might just make all the difference, as fares often shift. You can also enjoy considerable savings by opting for a longer stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and holiday rental type, ensuring you find the perfect Kiwi getaway.

Vrbo Trips: Effortless planning

Vrbo’s inventive Trip Board provides you with a dedicated space to plan new adventures, pick up where you stopped, or organise your travel plans. All the properties you’ve saved or booked are now neatly categorised under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/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:

  • Silverthorn Country Club (11.4 mi / 18.3 km)
  • Cabot Citrus Farms (13.1 mi / 21 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)
  • 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)
  • 7 Sisters Springs (11 mi / 17.6 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

When is the best time to visit Pine Island for a holiday rental?
The best time to visit Pine Island for a holiday rental is during the peak season from June to August. This vibrant period attracts sun-seekers and outdoor enthusiasts eager to soak up the sun on pristine beaches and enjoy water activities such as kayaking and paddleboarding. With temperatures typically ranging from 25 to 32 degrees Celsius, the warm weather makes it an ideal time for relaxation and exploration.June, in particular, is a popular month to experience the island's lively option, with plenty of opportunities for fresh seafood dining and local events that celebrate the unique culture of the area. The longer daylight hours provide ample time for outdoor adventures, whether you're strolling along the sandy shores or discovering the island's natural beauty.For those looking to save a bit on accommodation, consider planning your visit in November. This month offers a quieter experience, allowing you to enjoy the serene charm of Pine Island without the summer crowds. It's a lovely time for nature walks and birdwatching, as the cooler temperatures (around 20 to 25 degrees Celsius) create a comfortable environment for outdoor activities.
What are the top attractions in Pine Island?
In Pine Island, Florida, visitors can enjoy a range of attractions that highlight the area's natural beauty and local charm. The island is known for its serene beaches, such as Blind Pass Beach, which offers stunning views and opportunities for swimming and sunbathing. The nearby Pine Island Sound is great for kayaking, paddleboarding, and fishing, appealing to water sports enthusiasts.For those interested in wildlife, the Bokeelia area provides access to the vibrant ecosystems of the Charlotte Harbor Preserve State Park, where nature trails and birdwatching opportunities abound. Visitors can also explore the local art scene at the Pine Island Art Association Gallery, which showcases the work of local artists and hosts various community events throughout the year.The island is dotted with quaint restaurants and shops, particularly in the town of St. James City, where travellers can enjoy fresh seafood and local delicacies.
Are all fees included in the Pine Island holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Pine Island holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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 any discounts for Pine Island holiday homes?
You can find great discounts on holiday homes in Pine Island on Bookabach, 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 change or cancel my Pine Island holiday home booking on Bookabach?
To find Pine Island holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Pine Island?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Pine Island holiday home?
Book your Pine Island holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pine Island?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Pine Island to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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