We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals with a kayak in Pittsylvania County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Pittsylvania County

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Condo in Moneta

4.78 out of 5 average rating, 145 reviews

VOTED BEST Amenities Bernards Landing Kayak Grill

BERNARDS VACATION PROPERTIES -BOOKBERNARDS-Voted as one of the “BEST PLACES TO STAY” at Smith Mountain Lake- January issue of Laker Magazine ⭐️⭐️INDOOR POOL HOT TUB OPEN YEAR ROUND⭐️ ⭐️5G FAST WIFI-NEW⭐️ NEW UPDATED PATIO-BEST VIEWS KAYAK & TUBES-INCLUDED LINENS & TOWELS-INCLUDED, NEW WEBBER GRILL FOR GUESTS-INCLUDED ALL MOVIE,SPORTS OUTDOOR CHANNELS & MORE-INCLUDED TENNIS, RACKETBALL, AND PICKLE BALL RACKETS AND BALLS-INCLUDED ,OUTDOOR & INDOOR POOL ALL NEW FURNITURE, APPLIANCES & KING BED

Jan 10 – 17

G$36,632 GYD per night

Home in Moneta

4.93 out of 5 average rating, 15 reviews

Anchor’s Aweigh

Anchor's Aweigh! Relax with the whole family at this peaceful retreat. This property is located in an upscale subdivision with access to a community pool, tennis, pickle ball, basketball, boat ramp, and there's room for the boat trailer in the driveway. Located at the end of a cul-de-sac boasting over 200LF of lake waterfront. This home provides access close to Bridgewater Plaza and SML State Park. Come enjoy the 85" TV, outside covered gazebo, grill, 4 kayaks with paddles, and deep water dock.

Oct 9 – 16

G$38,191 GYD per night

Home in Sandy Level

4.92 out of 5 average rating, 36 reviews

Hycliff Lodge Mountain Retreat-Water Access

Enjoy the nature and tranquility of this private, 5 acre mountain home on Leesville Lake. Hycliff offers comfortable sleeping for 7 with 3 bedrooms and 2 full bathrooms. The open floor plan, cozy furnishings and a plethora of entertainment are sure to make some core family vacation memories. Hiking and fishing lovers are sure to enjoy the challenging, 1/10 mile walk to the water to your private, covered dock. The mountain and sunset views are stunning all year long from this gorgeous property.

Feb 7 – 14

G$41,544 GYD per night

Cabin in Pittsville

5.0 out of 5 average rating, 22 reviews

Waterfront Cabin on Leesville Lake!

This waterfront log cabin has everything you need to escape and live the lake life. With over an acre of lawn, a huge private shoreline, and a covered dock, you can enjoy one of Virginia’s best kept secrets without a worry. -Fire pit -Propane grill -Water toys, tubes, yard games, and fishing poles -Stocked kitchen -Kayak & canoe -Gym equipment -Dart board, putting green, pop-a-shot -Board games & puzzles -PS4 & Wii -Deep water off dock for swimming -Nearby hiking trails -Everything you need!

Sep 6 – 13

G$57,722 GYD per night

Cottage in Huddleston

4.82 out of 5 average rating, 127 reviews

A Nautical Nook on Smith Mountain Lake

A pristine, scenic, lovely 2 bed, 1 bath waterfront cottage set on about an acre of property gently tucked into a cove of Smith Mountain Lake. Private stylish cozy retreat for a couple or small family of 4, with graceful appointed furnishings. Designed open floor plan living area blending dining, kitchen, living room. Gently slopping yard to 24' x24' dock and private boat ramp. Stroll over to the fire pit in the evening after enjoying a day on the lake. Come and enjoy our slice of paradise!

Apr 19 – 26

G$83,892 GYD per night

Home in Huddleston

4.91 out of 5 average rating, 109 reviews

Lakefront Sunday Free Lift Dock HotTub Kayaks Pets

Beautiful Lakefront House Sunday Free(w/check in any weekday & stay thru Sat.night get Sun.night free) 1.68 Acres. HotTub. Amazing Views. No steps entrance or main floor. Gentle lot w/walkway to lake. Dock w/Boat Lift,Firepit w/Wood,Canoe,4 Kayaks/LifeVests, Bikes/Helmets, Screened Porch. Deck. Cleanest SML Water for Boat,Fish,Swim. Games/Activities for kids. Near Marina w/Boat Rentals & SML State Park. Family/Older Folks/Kids/Pets. Linens free. Lots of Parking. Apr/May Special $98 Mon.night

Jan 24 – 31

G$71,891 GYD per night

Guest suite in Moneta

5.0 out of 5 average rating, 24 reviews

Webb's Waterfront Retreat-Enjoy the Beach

Relax at this peaceful waterfront retreat. Kayak, paddleboard, swim, fish, or just sit on the sandy beach. Rent a boat or jet ski nearby or enjoy one of the fun local restaurants. This lower level apartment has easy parking and is just steps from the water. The unit has living/dining space, a separate bedroom, and a mini kitchen with refrig, microwave, and toaster oven. 600+ square feet. Wifi and tv are available. Free use of kayak or give the paddleboard a try. Life vests are available.

Oct 18 – 25

G$33,722 GYD per night

Home in Pittsville

4.97 out of 5 average rating, 161 reviews

Be Secluded on Leesville Lake in Bedford County VA

Gail & I came out of retirement to renovate this unique home with a completely new kitchen, vinyl plank flooring, new deck & new well in the Fall of 2019. This 3 bedroom lakehouse is very secluded within about an hour drive from Lynchburg, Roanoke or Danville. The dock and boat ramp are especially convenient. Keep an eye out for eagles, osprey, deer, turkeys, otters, geese & herons. You could watch eagles & osprey fishing in the lake from the upper deck, the lower deck or the dock.

Mar 10 – 17

G$40,666 GYD per night

Townhouse in Huddleston

5.0 out of 5 average rating, 27 reviews

Lakefront Walk-Out Condo w/Golf Course & Amenities

Relax with the whole family at our peaceful lake getaway! Our condo is a first floor, end unit with a gentle slope down to the lake, docks and a beach. Renovated in 2023, we added special touches to make you feel at home. Brand new beds, sofas, linens, appliances, LVP flooring throughout, whole house air purifier, down free bedding, multiple pillow choices, fully stocked kitchen, 2 paddle boards, kayak, games and so much more! This is our little getaway that we’d love to share with you!

Nov 4 – 11

G$44,372 GYD per night

Condo in Moneta

4.99 out of 5 average rating, 290 reviews

Lake Lover's Paradise

Come to the lake! This spacious one bedroom top floor end unit is uniquely located between Napoli by the Lake restaurant and large outdoor swimming pool. Fantastic views of the lake from the large deck! Sleeps 2 adults and 2 small children under three. The following amenities are provided during your stay (Subject to season and repair): 2 Outdoor Pools Exercise Room Boat & Jet Ski Rental 1 Indoor Pool Hot Tub Courtesy Boat Slips Beach & Boat Launch Area Tennis & Pickleball Courts

Oct 20 – 27

G$40,689 GYD per night

Home in Huddleston

5.0 out of 5 average rating, 14 reviews

Cedar Key Retreat

Situated on 200 yards of Witcher Creek shore line in Cedar Key Cove, this 3-bedroom house offers spectacular water and mountain views. Enjoy the quiet of a 3/4 mile no-wake zone that opens out to the main lake. Admire the lake view from the deck, sunroom, or covered patio. The lake itself is just steps away from the house which is nestled in a quiet, protected wildlife preserve and state forest where you can enjoy the tranquility of a 3-acre wooded lot and walks through the forest.

Dec 10 – 17

G$81,501 GYD per night

Home in Huddleston

4.98 out of 5 average rating, 138 reviews

LakeFront Paradise! Slide & Diving board

Million $$ Views!! This private 1-acre lakefront A-Frame retreat boasts gorgeous, wide water views and spectacular sunsets of Smith Mountain Lake, VA! Sit in one of the 4 outdoor living spaces and enjoy the spectacular view of the lake with mountains in the distance! Have a blast using the diving board and dock water slide! **Pets are permitted on a case by case basis -- ONLY after pre-approval. Please inquire before booking, see more info below**

Aug 25 – Sep 1

G$137,855 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Pittsylvania County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Huddleston

4.98 out of 5 average rating, 41 reviews

Smith Mountain Lake quiet cove w/ kayaks & firepit

Jan 1 – 8

G$74,157 GYD per night

Home in Gretna

4.93 out of 5 average rating, 82 reviews

Secluded Lakefront Cabin Resort: 5400sqft 6BR, 5ba

Jan 22 – 29

G$179,673 GYD per night

Home in Penhook

5.0 out of 5 average rating, 15 reviews

On The Rocks SML

Dec 15 – 22

G$144,357 GYD per night

Home in Moneta

5.0 out of 5 average rating, 37 reviews

Serenity & Sunsets-Family friendly home SML,2kings

Feb 10 – 17

G$79,594 GYD per night

Home in Penhook

4.96 out of 5 average rating, 25 reviews

Lakefront Oasis: Your Home Away from Home

Mar 8 – 15

G$144,181 GYD per night

Home in Huddleston

4.96 out of 5 average rating, 73 reviews

Knot Too Shabby- SML -Waterfront Home/ Boat Dock

Jan 23 – 30

G$84,145 GYD per night

Home in Huddleston

5.0 out of 5 average rating, 12 reviews

Gentle slope to deep, clear water.. Screened dock!

Sep 21 – 28

G$180,775 GYD per night

Home in Huddleston

4.98 out of 5 average rating, 50 reviews

Fun Spot 2 - Amazing Dock/Patio, Hot Tub & Kayaks

Nov 14 – 21

G$204,401 GYD per night

Destinations to explore