Discover Your Perfect Annandale Vacation Homes

Best Vacation Homes in Annandale

Cottage
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
US $407/Night 7 Nights - US $2,848
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House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 3 Baths 9 Guests 2152.78 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
US $493/Night 7 Nights - US $3,452
Hotel
Map-icon
like-icon7.8
Very Good
(303 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
US $118/Night 7 Nights - US $827
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $302/Night 7 Nights - US $2,112
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House
Map-icon
like-icon9.3
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 6 Guests 527.43 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $273/Night 7 Nights - US $1,909
Condo
Map-icon
like-icon9.6
Exceptional
(74 Reviews)
2 Bedrooms 1 Bath 6 Guests 950 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $207/Night 7 Nights - US $1,452
House
Map-icon
like-icon9.4
Exceptional
(12 Reviews)
2 Bedrooms 1 Bath 6 Guests 530 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $274/Night 7 Nights - US $1,918
House
Map-icon
like-icon10.0
Exceptional
(93 Reviews)
4 Bedrooms 2 Baths 15 Guests 3100 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $840/Night 7 Nights - US $5,878

Annandale Luxury Rentals

House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
6 Bedrooms 4 Baths 14 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $1,083/Night 7 Nights - US $7,583
House
Map-icon
like-icon9.6
Exceptional
(26 Reviews)
4 Bedrooms 3 Baths 12 Guests
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $880/Night 7 Nights - US $6,158
Cabin
Map-icon
7 Bedrooms 2 Baths 20 Guests 3054 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $879/Night 7 Nights - US $6,156
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
5 Bedrooms 3 Baths 12 Guests 4800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $874/Night 7 Nights - US $6,115
House
Map-icon
like-icon10.0
Exceptional
(42 Reviews)
5 Bedrooms 5 Baths 12 Guests 4000 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $832/Night 7 Nights - US $5,825
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
5 Bedrooms 3 Baths 10 Guests 2963 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $798/Night 7 Nights - US $5,584
New
House
Map-icon
8 Bedrooms 2 Baths 12 Guests 3000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $786/Night 7 Nights - US $5,504
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
5 Bedrooms 4 Baths 10 Guests
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $784/Night 7 Nights - US $5,487

Annandale Pet Friendly Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(47 Reviews)
4 Bedrooms 3 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $456/Night 7 Nights - US $3,194
Hotel
Map-icon
like-icon6.8
Good
(56 Reviews)
5 Baths 340.14 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $133/Night 7 Nights - US $931
Cabin
Map-icon
like-icon9.6
Exceptional
(97 Reviews)
4 Bedrooms 2 Baths 14 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $389/Night 7 Nights - US $2,725
Cottage
Map-icon
like-icon9.6
Exceptional
(9 Reviews)
3 Bedrooms 2 Baths 10 Guests 1900 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
US $442/Night 7 Nights - US $3,093
House
Map-icon
like-icon9.0
Exceptional
(31 Reviews)
3 Bedrooms 3 Baths 9 Guests 2148 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $418/Night 7 Nights - US $2,926
Cabin
Map-icon
like-icon9.4
Exceptional
(21 Reviews)
2 Bedrooms 1 Bath 6 Guests 816 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $307/Night 7 Nights - US $2,150
Cabin
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 1 Bath 9 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $408/Night 7 Nights - US $2,856
House
Map-icon
like-icon9.2
Exceptional
(52 Reviews)
3 Bedrooms 1 Bath 6 Guests 1600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $392/Night 7 Nights - US $2,743

Annandale Large Vacation Homes

Cabin
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
4 Bedrooms 3 Baths 12 Guests 2320 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
US $696/Night 7 Nights - US $4,872
star-icons-4
House
Map-icon
3 Bedrooms 3 Baths 12 Guests 2798.62 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $385/Night 7 Nights - US $2,695
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
5 Bedrooms 1 Bath 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $485/Night 7 Nights - US $3,395
House
Map-icon
1 Bedroom 1 Bath 10 Guests 1399.31 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $501/Night 7 Nights - US $3,507
House
Map-icon
like-icon9.8
Exceptional
(30 Reviews)
6 Bedrooms 2 Baths 14 Guests 2636 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
US $448/Night 7 Nights - US $3,136
House
Map-icon
like-icon9.8
Exceptional
(26 Reviews)
4 Bedrooms 2 Baths 10 Guests 2000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $513/Night 7 Nights - US $3,593
Cabin
Map-icon
like-icon9.8
Exceptional
(12 Reviews)
4 Bedrooms 2 Baths 10 Guests 2000 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $505/Night 7 Nights - US $3,533
House
Map-icon
like-icon9.6
Exceptional
(20 Reviews)
5 Bedrooms 2 Baths 10 Guests 2600 ft²
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $520/Night 7 Nights - US $3,637

Discover & compare premier experiences around Monticello

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 Annandale 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 Annandale

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation in this destination ensures you can enjoy the region's natural beauty and outdoor activities at their best, allowing for a more memorable stay in Annandale’s inviting surroundings.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, this area experiences peak visitation as travelers seek outdoor activities and scenic views around Annandale. Expect more lively atmospheres and higher demand for vacation rentals.

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

The vibrant fall foliage attracts visitors looking to enjoy picturesque landscapes and outdoor adventures, making it a popular time to visit this destination. Rental accommodations tend to be in higher demand during these months.

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

Off-Season Highlights

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Winter (December to February)

With colder weather and snow-covered scenery, winter sees fewer visitors seeking quiet retreats or winter sports, resulting in lower rental rates. This is an ideal time for those wanting a peaceful stay.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°F
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Spring (March to May)

As the region transitions from winter to warmer weather, fewer tourists visit, providing a quieter experience for those booking here. Spring offers a serene environment with blooming nature.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Annandale

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 with a fully equipped barbecue area to host cookouts after a day on the lake.
  • Relax by private or shared fire pits ideal for evening gatherings and marshmallow roasting.
  • Take advantage of spacious patios or decks perfect for outdoor dining and soaking up the local scenery.
  • Explore scenic walking paths or trails directly accessible from your rental for outdoor adventures.
  • Make use of well-maintained boat docks or slips if you plan to enjoy the lakes in this region.
  • Benefit from access to outdoor sports facilities, such as volleyball courts or basketball hoops, for active fun.
  • Unwind in landscaped gardens or lush lawns that provide peaceful outdoor spaces for relaxation.
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Family Activities

  • Lake Annandale: Spend quality time with your family enjoying fishing, swimming, or picnicking by the scenic waters of Lake Annandale, a central feature of this charming region.
  • The Annandale Historic District: Explore local history as you stroll through the historic district, discovering well-preserved sites and learning about the area's rich heritage.
  • Annandale Area Parks: Engage in outdoor activities at nearby parks that offer playgrounds, walking trails, and open spaces perfect for family outings and relaxation.
  • Local Community Events: Participate in seasonal community events and festivals that foster family fun and create memorable experiences here in the region.
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Adult Activities

  • Fishing on Clear Lake: You can enjoy a relaxing day of fishing here, renowned for its abundant fish species and tranquil waters.
  • Hiking and Nature Walks: Explore scenic trails around the area, offering peaceful walks and opportunities to observe local wildlife.
  • Golfing at nearby courses: Tee off at well-maintained golf courses that provide a great way to unwind while enjoying the area's natural beauty.
  • Exploring local parks: Discover the parks in this region, perfect for picnics, leisure activities, and appreciating the outdoor environment.

Annandale Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Keep an eye on regional calendars to align your visit with local festivals or activities that enhance your stay here.
  • Explore Natural Surroundings: Take advantage of the area’s scenic spots and outdoor recreation opportunities to experience the region's natural beauty firsthand.
  • Select the Right Property Location: Choose a vacation rental close to key attractions or convenient transport options to maximize your time here.
  • Connect with Local Resources: Utilize nearby visitor centers or community websites for insider tips and recommendations during your stay in this destination.

Transportation Options

  • Local Bus Services: Reliable bus routes connect you to key destinations within the region, making it easy to explore without a car.
  • Car Rentals: Renting a vehicle provides flexibility and convenience for discovering all that this destination has to offer in your own pace.
  • Taxi and Ride-Sharing: Taxis and ride-share services are readily available, offering quick transportation options around the area.
  • Airport Transfers: Efficient transfer services link the nearby airports to your vacation rental, ensuring a smooth arrival and departure experience.

Local Customs Options

  • Local Craftsmanship: The region is known for its traditional woodworking and handcrafted goods, reflecting the area's rich artisanal heritage.
  • Community Events: Participating in seasonal festivals and local gatherings offers an authentic experience of the area's welcoming spirit.
  • Seasonal Outdoor Activities: Enjoying activities like fishing and boating on nearby lakes is a common way residents embrace the region's natural beauty.
  • Food Traditions: Local eateries often celebrate regional flavors with seasonal specialties that highlight Minnesota's culinary heritage.

Annandale Vacation Rental Frequently Asked Questions

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 66 in the Annandale 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 Annandale. 

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 and contact the owner directly to understand their terms and any applicable fees.

5. Are pets allowed in vacation rentals near here?

Pet policies depend on the individual rental; you should check the listing description or reach out to the host to confirm if pets are permitted during your stay.

6. How do I ensure the vacation rental has the amenities I need?

Listings typically include detailed descriptions of the amenities offered, but for specific requests or questions, contacting the property owner beforehand is recommended.

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

Minimum stay requirements can differ between properties, so it’s best to review each listing carefully or inquire with the owner directly before booking.

8. What is the check-in and check-out process at vacation rentals in this region?

Check-in and check-out procedures are outlined in the listing details, but contacting the property owner allows you to clarify any special instructions or coordinate your arrival.