Discover Your Perfect Timbercrest Vacation Homes

Best Vacation Homes in Timbercrest

New
House
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4 Bedrooms 2 Baths 8 Guests 2091 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $222/Night 7 Nights - US $1,553
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House
Map-icon
like-icon9.6
Exceptional
(7 Reviews)
4 Bedrooms 3 Baths 11 Guests 2131.25 ft²
  • Hot Tub
    Hot Tub
  • View
    View
More amenities
US $276/Night 7 Nights - US $1,931
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House
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $463/Night 7 Nights - US $3,241
House
Map-icon
like-icon10.0
Exceptional
(14 Reviews)
2 Bedrooms 2 Baths 6 Guests 1445 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $173/Night 7 Nights - US $1,212
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House
Map-icon
like-icon9.5
Exceptional
(14 Reviews)
4 Bedrooms 2 Baths 3 Guests 1399.31 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $177/Night 7 Nights - US $1,242
House
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $142/Night 7 Nights - US $992
Cottage
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $117/Night 7 Nights - US $819
Cabin
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 4 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $214/Night 7 Nights - US $1,499

Timbercrest Luxury Rentals

Villa
Map-icon
like-icon9.8
Exceptional
(6 Reviews)
5 Bedrooms 3 Baths 15 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $524/Night 7 Nights - US $3,668
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $454/Night 7 Nights - US $3,181
House
Map-icon
4 Bedrooms 2 Baths 6 Guests
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
US $413/Night 7 Nights - US $2,888
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $333/Night 7 Nights - US $2,331
House
Map-icon
4 Bedrooms 2 Baths 10 Guests 2152.78 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $327/Night 7 Nights - US $2,289
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House
Map-icon
like-icon9.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 6 Guests 1862.16 ft²
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $299/Night 7 Nights - US $2,093
New
star-icons-3
House
Map-icon
4 Bedrooms 2 Baths 8 Guests 2088.2 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $290/Night 7 Nights - US $2,029
House
Map-icon
like-icon9.0
Exceptional
(11 Reviews)
3 Bedrooms 2 Baths 6 Guests 1976 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $287/Night 7 Nights - US $2,007

Timbercrest Pet Friendly Vacation Rentals

House
Map-icon
like-icon9.4
Exceptional
(6 Reviews)
2 Bedrooms 2 Baths 7 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $240/Night 7 Nights - US $1,681
star-icons-4
House
Map-icon
like-icon9.4
Exceptional
(22 Reviews)
3 Bedrooms 2 Baths 8 Guests 1334.72 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
US $91/Night 7 Nights - US $638
House
Map-icon
like-icon10.0
Exceptional
(68 Reviews)
3 Bedrooms 2 Baths 8 Guests 2300 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
US $216/Night 7 Nights - US $1,511
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Bed & Breakfast
Map-icon
like-icon8.0
Excellent
(63 Reviews)
4 Bedrooms 4 Baths 12 Guests 204.51 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $165/Night 7 Nights - US $1,155
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $261/Night 7 Nights - US $1,828
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 3 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $233/Night 7 Nights - US $1,630
House
Map-icon
like-icon9.8
Exceptional
(7 Reviews)
3 Bedrooms 2 Baths 10 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $284/Night 7 Nights - US $1,985
House
Map-icon
like-icon9.6
Exceptional
(18 Reviews)
3 Bedrooms 2 Baths 7 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $163/Night 7 Nights - US $1,142

Timbercrest Large Vacation Homes

House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
4 Bedrooms 3 Baths 11 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $316/Night 7 Nights - US $2,215
star-icons-3
Bed & Breakfast
Map-icon
like-icon9.3
Exceptional
(116 Reviews)
8 Bedrooms 2 Baths 4 Guests 279.87 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $159/Night 7 Nights - US $1,113
Villa
Map-icon
5 Bedrooms 4 Baths 22 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $643/Night 7 Nights - US $4,502
House
Map-icon
4 Bedrooms 2 Baths 10 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $315/Night 7 Nights - US $2,205

Why Choose Rent By Owner for your Timbercrest Vacation Rental Homes?

What makes our Vacation Rentals 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 Timbercrest

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can enhance your experience, so consider planning your stay during the region’s optimal seasons when the weather and local events align to create a memorable vacation in the area.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area experiences warm daytime temperatures and pleasant evenings, making it an ideal time to enjoy the outdoors and explore local scenery.

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

Fall offers comfortable weather with mild temperatures perfect for outdoor activities and enjoying the peaceful ambiance of this destination.

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)

In summer, the region sees higher temperatures and increased humidity, which might be less favorable for outdoor pursuits but still suitable for indoor relaxation at your vacation rental.

Average Temperature Daytime: 85°F to 95°F - Nighttime: 65°F to 75°F
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Winter (December to February)

Winter months tend to be cooler, offering a quieter experience for those seeking a peaceful retreat away from peak times in this part of Florida.

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

Weekly Weather Forecast for Timbercrest

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 a private outdoor pool to relax and unwind during your stay.
  • Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
  • Explore well-maintained gardens and landscaped yards that offer serene outdoor scenery.
  • Utilize outdoor grilling areas to prepare delicious meals with family and friends.
  • Benefit from shaded lounging zones ideal for relaxing in the warm Florida sun.
  • Make use of outdoor sports facilities such as basketball courts or volleyball nets, if available.
  • Discover scenic walking or biking trails nearby to explore the natural beauty of the area.
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Family Activities

  • Lake Helen Historic Downtown Tour: Discover the charming history of this area through a self-guided walk around Lake Helen's historic downtown, perfect for family outings that blend education and fun.
  • Valencia College Science Center: Engage in interactive science exhibits geared toward younger visitors, making it an ideal stop for families seeking educational activities in the region.
  • Central Florida Nature Trails: Embark on scenic hiking or biking adventures along nature trails nearby, offering fresh air and wildlife encounters suitable for all ages.
  • Local Community Events: Attend seasonal festivals or outdoor concerts held here, providing lively entertainment and cultural experiences for the whole family.
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Adult Activities

  • Golfing at Lake Region Golf Club: You can enjoy a round of golf at this scenic club, perfect for unwinding and soaking in the tranquil views of the area.
  • Exploring local parks and nature trails: Take advantage of nearby parks that offer peaceful walking and biking paths amidst Florida’s natural beauty.
  • Visiting historic sites in Lake Helen: Discover the region’s rich history by exploring charming sites that highlight its unique heritage.
  • Attending community events and festivals: Engage with local culture through seasonal events and festivals that showcase the vibrant community here.

Timbercrest Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and attractions: Take advantage of nearby eateries and scenic spots to experience the region's authentic charm during your stay.
  • Plan outdoor activities: Make the most of the area's natural beauty by scheduling outdoor adventures like walking or nature exploration right from your vacation rental.
  • Check for seasonal events: Engage with community events or festivals that showcase the local culture, adding a memorable touch to your visit here.
  • Utilize local resources: Use the area’s visitor centers or online guides to uncover hidden gems and insider tips for a truly enriching experience.

Transportation Options

  • Private Car Rental Services: Renting a car allows you to explore this destination with flexibility and convenience, providing easy access to all the regional attractions.
  • Public Transportation (Bus Services): Local bus routes connect you to key areas within the region, making affordable travel around here straightforward.
  • Taxis and Ride-Sharing Apps: Taxis and ride-sharing options offer quick and reliable transportation for getting around the area comfortably and efficiently.
  • Airport Transfers: Shuttle and private transfer services facilitate smooth arrivals and departures at nearby airports, ensuring stress-free travel in this part of Florida.

Local Customs Options

  • Southern Hospitality: Visitors often notice the warm and welcoming attitude that reflects the region's friendly community spirit in Timbercrest and nearby Lake Helen.
  • Local Festivals: The area celebrates its traditions through seasonal events that highlight community involvement and regional pride.
  • Retirement Community Respect: Respect for elders and a tranquil lifestyle are central to local customs, shaping the relaxed atmosphere here.
  • Nature Appreciation: Emphasizing outdoor activities and environmental preservation is a common custom embraced by locals and visitors alike in this Florida destination.

Frequently Asked Questions About Timbercrest?

2. Which vacation homes in Timbercrest are best for families?

If you are looking for a family-friendly vacation home in Timbercrest, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Timbercrest:

3. How many Rentbyowner vacation rentals are available in Timbercrest?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 90 in the Timbercrest area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Timbercrest. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand the refund options and any associated fees.

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

Yes, each vacation rental has its own set of house rules and restrictions, which are detailed in the listing. It’s recommended to read these carefully and reach out to the owner if you have any questions.

6. How do I secure my reservation and what payment options are accepted?

Reservations are secured through the listing platform, typically requiring a deposit or full payment upfront. Accepted payment methods can include credit cards, debit cards, or other online payment options; details are provided within each listing.

7. What is the check-in and check-out process like at vacation rentals here?

Check-in and check-out procedures are specified in the property listing. Many rentals utilize keyless entry systems or lockboxes for convenience. Contact the owner if you need specific instructions or assistance.

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

Minimum stay requirements depend on the individual property and the time of year. You should verify these details during the booking process or by contacting the property owner directly.

Timbercrest Top Rated Vacation Rentals

Bed & Breakfast
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $194/Night 7 Nights - US $1,361
star-icons-3
House
Map-icon
like-icon9.4
Exceptional
(125 Reviews)
1 Bedroom 1 Bath
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $163/Night 7 Nights - US $1,142
House
Map-icon
like-icon9.2
Exceptional
(20 Reviews)
3 Bedrooms 2 Baths 6 Guests 1864 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $200/Night 7 Nights - US $1,400
Cabin
Map-icon
1 Bedroom 1 Bath 2 Guests 500 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $214/Night 7 Nights - US $1,499
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $206/Night 7 Nights - US $1,439
House
Map-icon
1 Bedroom 1 Bath 2 Guests 139.93 ft²
  • Pool
    Pool
  • Parking
    Parking
More amenities
US $78/Night 7 Nights - US $546
House
Map-icon
like-icon10.0
Exceptional
(34 Reviews)
3 Bedrooms 2 Baths 7 Guests 1765 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $300/Night 7 Nights - US $2,103
Cottage
Map-icon
like-icon10.0
Exceptional
(23 Reviews)
1 Bedroom 1 Bath 5 Guests 468 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
US $113/Night 7 Nights - US $788