Vacation rentals with a kayak in Orleans

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Orleans

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Yarmouth

4.99 out of 5 average rating, 174 reviews

Serenity Views | Waterfront | King | Firepit Kayak

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!!

Apr 10 – 17

G$95,106 GYD per night

Guest favorite

Cottage in Eastham

4.95 out of 5 average rating, 207 reviews

The Breeze Overlooking Minister's Pond

Welcome to an absolutely spotless, pristine, romantic cottage directly on a freshwater pond. Centrally located in beautiful Eastham, the Breeze is within walking distance to the Salt Pond Museum and Visitor Center and hiking trails. Take one of the electric bikes provided and hop on the bike path (the CCRT) which is just down the street. Kayak or canoe on the pond. Featured on WNAV "Romantic Winter Getaways". Award winning recommendations guide provided with each stay. *Sat-Sat in July & Au

Oct 8 – 15

G$55,366 GYD per night

Superhost

Home in Brewster

4.87 out of 5 average rating, 171 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

Jun 1 – 8

G$104,334 GYD per night

Guest favorite

Guest suite in Yarmouth

4.83 out of 5 average rating, 124 reviews

Cape EsCape:2 Rm Private Suite, EZ walk to beaches

location, LOCATION; comfy, contemporary newly renovated (‘21) private bedrm & family rm 0.4mile from neighborhd river-beach, 0.9mi from row of ocean beaches. Separate private entrance. A/C. Queen bed. Outside space with picnic table, chairs, & hammock. Beach chairs provided. W/in 5 min walking distance of bakeries, mini-golf, restaurants, shopping, bike trail, kayaking, & more. Bikes for guests. Child/infant friendly. If you need anything, tell me; please don’t wait & note it in your review.

Nov 6 – 13

G$25,433 GYD per night

Guest favorite

Home in South Yarmouth

4.93 out of 5 average rating, 209 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

✅ We keep rates low by you bringing your own sheets & towels OR linen service is $125. ✅ Smart TVs in LIving Room & 2 BRs ✅ Waterfront hot tub-Open year round ✅ Fully equipped kitchen w/Carrera marble countertops ✅ Gas Fireplace in LR ✅ High quality down comforters & pillows ✅ Level backyard to lake ✅ Dock for swimming and fishing ✅ 2 kayaks & 2 SUPs ✅ Deck w/sitting & dining area ✅ Patio w/seating & gas fire pit ✅ Sleeps 7 ✅ Pet fee $30/day ✅ Waterfront ✅ W/D Locally managed

Jan 11 – 18

G$68,219 GYD per night

Guest favorite

Tiny home in S. Yarmouth

4.88 out of 5 average rating, 541 reviews

Romantic Cottage w/ Bikes, Paddle Boards & Kayaks

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

Nov 11 – 18

G$36,302 GYD per night

Guest favorite

Cottage in Falmouth

4.93 out of 5 average rating, 136 reviews

“Cozy Cottage” on Great Bay

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.” Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach.We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

Nov 24 – Dec 1

G$38,808 GYD per night

Guest favorite

Home in Yarmouth

5.0 out of 5 average rating, 248 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

Jan 21 – 28

G$120,150 GYD per night

Guest favorite

Home in Dennis

4.95 out of 5 average rating, 151 reviews

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

Feb 8 – 15

G$52,597 GYD per night

Guest favorite

Apartment in East Orleans

4.94 out of 5 average rating, 259 reviews

Cozy Waterfront Apartment, Private Beach Access

Hello to all of my future guests. I want to wish you all well and safety in these uncertain times. I can assure you that this property is safe, private, spotless and affords you access to a beautiful private beach. I have updated the apartment to include a microwave and two kayaks. We are implicating extra sanitizing and cleaning measures to ensure the apartment is clean and safe for each guest! Please stay safe, optimistic, and let me know of any concerns. Sincerely, Patty

Feb 15 – 22

G$45,629 GYD per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 153 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Sep 27 – Oct 4

G$21,316 GYD per night

Guest favorite

Guesthouse in Yarmouth

4.96 out of 5 average rating, 183 reviews

One bedroom guest house on beautiful Cape Cod

Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.

Nov 7 – 14

G$35,984 GYD per night