
Holiday rentals with a kayak in Orange County
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Orange County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

La Vita Bella at Lake Anna, Lake Front Resort Home
Live the Beautiful Life at La Vita Bella at Lake Anna. This gorgeous and spacious 6000+ SqFt home sits on a hill overlooking Lake Anna's most coveted cove. Take in morning sunrises with your coffee from one of two porches or make your way down to your private dock and watch the birds dive and fish jump. Enjoy time on the water exploring the cove in the two kayaks or take dip in the lake. This is a special place, and you and your guests will find new levels of relaxation while enjoying your stay.

Blue House and a Pool
Relax at Lake Anna with friends and family at your own pool, hot tub and dock. Blue house boasts numerous spaces for entertaining and private chill time. House features 4 bedrooms, 3 large couches and 3 full bathrooms. The gourmet kitchen is fully stocked and ready for a home cooked meal after a full day on the lake. Tim's at Lake Anna is a short car ride or boat ride to enjoy a meal and cocktail. The Cove and Lake Anna Plaza at the 208 bridge are close by including boat and jet ski rentals.

Dog Friendly w/fence | Lake | Hot Tub| Dock Slip
Welcome to "The Shack", affectionally named after our parents’ and grandparents’ summer getaway on the Massachusetts Bay. The Shack is a renovated 4 BR / 6 bed, lake access, deep water cove, with a covered boat slip, hot tub, kayaks and firepit situated on 1 acre quiet cul-de-sac and dog friendly with a fenced yard. Our family friendly home is located on the Public Side of Lake Anna with over 2,200 sq ft of living space spread out over two levels. Short walk to the covered dock on Lake Anna.

The Lake Lodge: Private Slip, Lake Access, Hot Tub
Welcome to the Lake Lodge! You're invited to this peaceful retreat among a canopy of trees. The home is a 3 minute walk to the lake (public side), with a private slip, HOA sitting area, & boat ramp. When you aren't admiring the lake views from the HOA dock, savor the forested yard with built in firepit, cozy hot tub, & gigabit WIFI. After a long day of fishing, boating, or hiking, the home welcomes you with a stocked kitchen, outdoor grill, TVs in each room & a soaking tub. Relaxation awaits!

Sunrise view - Open water front - Dog Friendly
Relax with the whole family at this peaceful and recently updated lakefront home with panoramic views of Lake Anna. Beautifully located in a safe neighborhood on the public side of the lake, this fantastic dog-friendly property features a huge water front lawn with shady trees, a private dock complete with a boat house, fire pit, and expansive decks. The property offers a wealth of amenities, including a water slide, kayaks, paddle board, paddle boat, lawn games, and other relaxing features.

Lakefront at Turtle Cove
Enjoy the lake life in a peaceful quiet cove on the gorgeous large lake within Lake of the Woods. When not enjoying the newly renovated home with a vaulted ceiling great room, huge screened porch, and a desk and flat screen TV in each room, you can swim, float, kayak, or paddleboard in the quiet, secluded cove, or enjoy the 9 beaches or 2 community pools. Catch fish off the dock in one of the best fishing coves on the lake, and then warm up at night by the fire pit . Great for families.

Secluded Lakefront | Private Pool | Dock | Hot Tub
**Discover Ultimate Luxury at LesLee at the Lake: a Deep Water Lakefront Haven with Private Inground Pool, Hot Tub, and Dock** Nestled on the public side of Lake Anna, this picturesque 2.63-acre secluded property offers stunning waterfront views, a boat house for easy water access, and a lakefront fire pit. Our expansive and luxurious 9,000 sq. ft. home with game room, spacious kitchen, and movie theater, is ideal for an unforgettable escape and perfect for accommodating large groups.

Home with beautiful mountain and river views
Welcome to the Madison House! This custom designed and built estate rests on a knoll overlooking 13.5 private acres on the Robinson River in rural Madison County, VA. Views of the Blue Ridge Mountains and direct Robinson River frontage makes this property a perfect destination for all four seasons. The outdoor space is ideal for friends and family gatherings and is ideally located near restaurants, wineries and breweries. The indoor space is both spacious and cozy for ample relaxing.

Lakefront Villa on Lake Orange VA
In this 13.4 acres of wood and surrounded by the lake including half an acre private pond for fishing and have a nature walk through the wooded area and the peninsula. Quarter of a mile from the property on the other side of the lake there is a fishing bait store and boat rental. Whether you're seeking a peaceful retreat or an active lakeside adventure, our villa offers the best of both worlds. Book your stay today and experience the beauty and tranquility of Lake Orange in style. I

Waterfront retreat w/private dock/hot tub/kayaks
Homeport Harbor is the ultimate lake vacation home! Unwind in this spacious, cozy waterfront retreat located on the public side of Lake Anna! This 1,800 sq ft. home is located on one acre and is beautifully decorated; including completely all brand new furniture, kitchen upgrades and new mattresses throughout. Spend your days relaxing at the water’s edge on the private dock, screened in porch or large deck and your evenings roasting marshmallows gathered around the built-in fire-pit.

Life on the Lake, enjoy the peace and kayaks
Located within 20 minutes of both Fredericksburg and Culpeper, Virginia, this 2000 square foot home offers lakefront living on the 24-acre Keaton’s Lake within the gated community of Lake of the Woods. Keaton’s lake is ideal for fishing, swimming, kayaking or just lounging on the hammock or by the firepit enjoying the peaceful setting and beautiful view. Guests can also enjoy the 500 acre Main Lake and its beaches and parks.

Lake Anna Getaway • HotTub, GameRoom & Lake toys
Looking for lake access without the crowds? This beautifully designed home offers access to a private community boat slip, paddleboards, and peaceful surroundings—perfect for families or small groups seeking a relaxing escape. Enjoy evenings by the firepit, game nights in the open-concept living room, or morning coffee on the deck surrounded by nature. Just minutes from dining, wineries, and local fun.
Popular amenities for kayak rentals in Orange County
House rentals with a kayak

Harrison Hideaway

*Fall Fun*|4BR Lakefront|Fireplace| Firepit|BBQ

Jones’n on The Lake-Dog Friendly-Lake Access Home

Paradise Found: Lakefront Home in Locust Grove

5BR Wellness Retreat-Hot Tub+Cold Plunge+Sauna+Gym

Sunset Cove Waterfront, Sleeps 14 - Pet Friendly!

Lakefront Cabin Boat slip Wifi Fishing Firepit

Beautiful Lakehouse near Fredericksburg VA
Other holiday rentals with a kayak

Comfy Room by the Lake

6BR Lakefront Lake Anna, Views, Boat Dock, Hot Tub

Porch & Paddle

The Best Views on Lake Anna and Deepwater Dock!

Stone Bridge Farm - 1 BR Riverfront ADA Apartment

Lakefront Luxury - 10BR, Pool w/ Heat, Hot Tub

Cozy Farm getaway on Lake Anna

Lakeside Fall Retreat / Foliage & Firelight Nights
Destinations to explore
- Rentals with breakfast Orange County
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- Rentals with lake access Orange County
- Rentals with outdoor seating Orange County
- Cottage rentals Orange County
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- Rentals with a fireplace Orange County
- Flat rentals Orange County
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- Rentals with a washing machine and dryer Orange County
- Rentals with a firepit Orange County
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- Rentals with a kayak Virginia
- Rentals with a kayak United States
- Shenandoah National Park
- Kings Dominion
- Luray Caverns
- Early Mountain Winery
- Downtown Mall
- James Monroe's Highland
- Lake Anna State Park
- Blenheim Vineyards
- Prince Michel Winery
- Cardinal Point Winery
- Glass House Winery
- University of Virginia
- John Paul Jones Arena
- Shenandoah River Outfitters
- Monticello
- Jiffy Lube Live
- White Lotus Eco Spa Retreat
- The Rotunda
- Cooter's Place
- Grand Caverns
- IX Art Park
- White Oak Lavender Farm & The Purple WOLF Vineyard
- James Madison's Montpelier
- Fredericksburg Battlefield Visitors Center




