Vacation rentals with a kayak in Orleans

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Top-rated kayak rentals in Orleans

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Top guest favorite

A spacious deck overlooks the tranquil waterfront, featuring a large dining table surrounded by comfortable chairs. Lounge seating is arranged at one end, offering inviting views of the nearby trees and water under a clear blue sky.

Home in South Yarmouth

4.95 out of 5 average rating, 238 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

✅All linens provided & beds made ✅Smart TVs in living rm & 2 bdrms ✅Waterfront hot tub for 6 -Open year round ✅Fully equipped kitchen w/Carrera marble counters ✅Large waterfront dining rm ✅Gas Fireplace in living rm ✅High quality down comforters & pillows ✅Level backyard to lake - great for games ✅Dock for swimming & fishing ✅2 kayaks & 2 SUPs / beach chairs ✅Deck w/sitting & dining area ✅Patio w/seating & gas fire pit ✅Sleeps 7 ✅Pet fee $30/day ✅Waterfront ✅W/D Locally managed

Top guest favorite

Cottage in Yarmouth

5 out of 5 average rating, 221 reviews

Serenity Views | Waterfront | KingBed | Kayaks SUP

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!

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Home in Brewster

4.87 out of 5 average rating, 211 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.

Guest favorite

Cottage in South Dennis

4.97 out of 5 average rating, 120 reviews

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Welcome to the Bayside Retreat! Enjoy the Real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & *new high-end sofas in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps 🛋️ Comfy Furnishings➕Stocked Kitchen Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

Top guest favorite

Cottage in Dennis

4.98 out of 5 average rating, 186 reviews

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

Top guest favorite

An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.

Home in Yarmouth

5 out of 5 average rating, 157 reviews

Relax & Entertain | King Beds * Sauna * Bar Shed

Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, fire pit, and grill. The fenced backyard offers beach gear, paddle boards, and lounge area. We are perfectly located just 5–20 minutes from top spots, making it your ideal home base. With premium amenities, thoughtful touches like linens and towels provided, and space to relax and play, your perfect escape starts here.

Guest favorite

A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. The light wood floor complements the bright blue walls, while a flat-screen TV and a coffee table with remote sit within the space. Natural light filters through large glass doors, overlooking a private patio.

Cottage in Yarmouth

4.92 out of 5 average rating, 479 reviews

MODERN 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

Top guest favorite

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

5 out of 5 average rating, 311 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

Guest favorite

A charming antique Cape Cod home is framed by a white picket fence and surrounded by lush greenery. The exterior features a gray wood shingle facade and multiple windows. Two red adirondack chairs are positioned on the front porch, inviting relaxation amidst the serene garden.

Home in Orleans

4.97 out of 5 average rating, 35 reviews

1850 Orleans Antique Home with Path to Arey’s Pond

Make memories at this private family and pet-friendly 3 BR Orleans antique Cape Cod home with access to Arey’s Pond. Kayak and paddle-board directly to Little Pleasant Bay and beyond. The property was once home to the town tavern on Old County Road en route to Orleans. Enjoy the wrap-around 3 season porch. Antique home with bath and other renovations that were recently completed. We want to share this unique property with those who appreciate the history. Please ask questions!

Top guest favorite

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

Home in Dennis Port

4.96 out of 5 average rating, 201 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.

Guest favorite

A serene outdoor space features two blue Adirondack chairs positioned near a stone grill. A red kayak rests beside the seating area, surrounded by lush greenery and blooming yellow flowers. A small outdoor heater is also present, providing comfort in the tranquil setting.

Apartment in East Orleans

4.95 out of 5 average rating, 295 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

Guest favorite

A serene dock extends over calm waters, featuring two Adirondack chairs positioned beside vibrant potted flowers. Lush greenery frames the scene, providing a peaceful backdrop for relaxation. The setting invites guests to unwind and enjoy the tranquility of the freshwater pond.

Cottage in Eastham

4.95 out of 5 average rating, 242 reviews

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.