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Perry Winter Rental

Cottage
Map-icon
like-icon10.0
Exceptional
(44 Reviews)
1 Bedroom 1 Bath 4 Guests 400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $148/Night 7 Nights - US $1,039
US $100/Night 7 Nights - US $700
Cottage
Map-icon
like-icon10.0
Exceptional
(13 Reviews)
1 Bedroom 1 Bath 3 Guests 200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $93/Night 7 Nights - US $653
Apartment
Map-icon
like-icon9.8
Exceptional
(7 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $173/Night 7 Nights - US $1,213
Cabin
Map-icon
2 Bedrooms 1 Bath 6 Guests 400 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $314/Night 7 Nights - US $2,199
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
4 Bedrooms 2 Baths 8 Guests 1800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $283/Night 7 Nights - US $1,984
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
3 Bedrooms 2 Baths 12 Guests 1800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $664/Night 7 Nights - US $4,648
House
Map-icon
like-icon9.8
Exceptional
(29 Reviews)
4 Bedrooms 2 Baths 7 Guests
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $431/Night 7 Nights - US $3,018
Villa
Map-icon
like-icon9.4
Exceptional
(8 Reviews)
5 Bedrooms 4 Baths 16 Guests 3421 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $474/Night 7 Nights - US $3,320
House
Map-icon
like-icon8.0
Excellent
(1 Review)
3 Bedrooms 2 Baths 6 Guests 1620 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $310/Night 7 Nights - US $2,169
New
House
Map-icon
3 Bedrooms 3 Baths 10 Guests 1400 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
US $727/Night 7 Nights - US $5,090
House
Map-icon
like-icon10.0
Exceptional
(49 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $339/Night 7 Nights - US $2,371

Discover & compare premier experiences around Tallahassee

We understand the importance of quality and reliability in your travel experiences. That's why we've curated options from the most reputable tour and activity providers globally, ensuring you have access to top-tier adventures.

Why Choose Rent By Owner for your Perry Winter Rental?

What makes our Winter Rental special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Perry

When should you plan your Winter Rental stay?

Finding the ideal time to vacation here can enhance your experience and ensure you enjoy the region's pleasant winter climate, making it an excellent choice for seasonal stays through RentByOwner.com in Perry, Florida, USA.

Peak Season Highlights

spring
Spring (March to May)

During spring, the region experiences pleasant weather ideal for enjoying outdoor activities and exploring this destination’s natural beauty.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Fall offers comfortable temperatures and a quieter atmosphere, making it an excellent time to experience the area's calm charm without the peak crowds.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Summer (June to August)

Summer can be quite hot and humid here, but it's also a great time to enjoy the region's water-based activities with fewer visitors around.

Average Temperature Daytime: 85°F to 95°F - Nighttime: 70°F to 75°F
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Winter (December to February)

While winter is considered off-peak, mild temperatures make it appealing for those seeking a relaxing escape in a cozy setting within this destination.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Perry

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor grilling amenities to prepare meals surrounded by the scenic views of the region.
  • Benefit from spacious patios or decks ideal for relaxing or dining al fresco in the fresh air.
  • Take advantage of private pools or hot tubs designed for comfort and leisure during your stay.
  • Explore natural surroundings with access to nearby boat docks or fishing areas.
  • Experience outdoor sports facilities such as tennis courts or volleyball courts available on site.
  • Relax in outdoor fire pits perfect for evenings under the stars in this welcoming destination.
  • Utilize well-maintained yards or gardens that offer peaceful outdoor spaces for strolling or reading.
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Family Activities

  • Manatee Springs State Park Explore the natural beauty of this nearby park, where you can enjoy swimming, kayaking, and observing local wildlife in a family-friendly environment.
  • Perry Splash Pad & Playground Spend a fun-filled day at this local splash pad and playground, perfect for children to cool off and play in a safe, supervised setting.
  • Suwannee River Adventures Experience boat tours and river activities that offer families a chance to discover the scenic wilderness surrounding the region.
  • Local Wildlife Viewing Visit nearby nature areas where you can spot diverse bird species and other native wildlife, making it an educational outing for all ages.
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Adult Activities

  • Fishing on the Withlacoochee River: Spend a relaxing day casting your line in the region's renowned waters, known for their excellent freshwater fishing opportunities.
  • Exploring Lake City: Discover nearby Lake City, where you can enjoy boating, paddleboarding, or simply unwinding by the tranquil lakeside.
  • Wildlife Watching at Torreya State Park: Observe diverse native species and enjoy scenic hikes in this expansive park that showcases the natural beauty of the area.
  • Visiting Local Nature Trails: Take advantage of the numerous nature trails around here, perfect for walking or biking amid lush Florida landscapes.

Other Places to Stay in Perry, FL

Perry Train Depot
Taylor County Historical Society
Doctors Memorial Hospital
Taylor County Sports Complex
Hampton Springs

Perry Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Waterways: Take advantage of the region’s abundant lakes and rivers to enjoy kayaking or fishing during your stay in Perry, Florida.
  • Visit Seasonal Events: Check out local seasonal festivals or markets that showcase the area’s unique culture and community spirit.
  • Plan Outdoor Activities: Make the most of the natural surroundings by engaging in outdoor activities like birdwatching or nature walks around this destination.
  • Discover Nearby Nature Reserves: Spend time exploring nearby protected areas to experience the diverse flora and fauna the region offers.

Transportation Options

  • Personal Vehicles: Renting or using your own car offers flexible transportation to explore the region around Perry, Florida, and access your winter rentals with convenience.
  • Taxi Services: Local taxi providers provide reliable point-to-point transportation, making it easy to get around here without the need for personal vehicles.
  • Shuttle Services: Shuttle options are available for quick, direct travel between key locations within the area, ideal for exploring the nearby attractions or reaching your stay seamlessly.
  • Public Transportation: Public bus services connect various parts of the region, providing an economical way to navigate around Perry while enjoying the local scenery.

Local Customs Options

  • Gator Hunting and Wildlife Viewing: Engaging with the local wildlife, especially alligators, is a common activity that reflects the region's natural environment in Perry, Florida.
  • Southern Hospitality and Politeness: Visitors are often greeted with warm hospitality and courteous manners characteristic of this welcoming southern community.
  • Folk Music and Community Gatherings: Participating in or observing traditional folk music sessions and local festivals offers insight into the area's cultural heritage.
  • Religious Celebrations and Festivals: The community's strong faith is evident through various religious events and seasonal celebrations held throughout the year.

Perry Winter Rental Frequently Asked Questions

1. How many Winter Rentals are available in Perry?

Currently, the total number of properties listed by RBO in 2026 is over 22 in the Perry area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Perry. 

2. What is the cancellation policy for winter rentals in Perry, Florida?

Cancellation policies vary depending on the individual listing. You should review the specific owner's policy on the property page or contact the owner directly for detailed information.

3. How do I secure my reservation for winter stays in this area?

Reservations are typically secured through a booking process that requires confirmation and payment. Details are available on each listing page, and you can reach out to the owner if you have any questions about securing your stay.

4. Are there any house rules or restrictions I should be aware of before booking?

Yes, each property has its own set of house rules and restrictions listed on the property page. It's best to read these carefully before confirming your reservation to ensure a smooth stay.

5. What amenities are usually included in winter rentals here?

Amenities vary by property but often include essentials like heating, kitchen facilities, and Wi-Fi. For a complete list of amenities, please check the specific listing details or contact the property owner directly.

6. Is there a minimum stay requirement for booking in this destination?

Minimum stay requirements differ based on the property and season. You can find this information on the listing page or by contacting the owner to clarify any specific stay length needs.

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  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
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US $99/Night 7 Nights - US $693
RV Rental
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like-icon4.7
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1 Bedroom 1 Bath 6 Guests
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
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US $75/Night 7 Nights - US $525
Cabin
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1 Bedroom 1 Bath 4 Guests
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US $175/Night 7 Nights - US $1,225