
Holiday rentals with a kayak in Oak Bluffs
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Oak Bluffs
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for kayak rentals in Oak Bluffs
House rentals with a kayak

Life is Good Rentals in Mashpee

Snug Harbor - West Falmouth, Cape Cod.

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

Falmouth Summer Fun–Game Barn-Dog Friendly!

Mashpee Manor Pool House

Swan nest escape

25 Menemsha Rd., Popponesset, pond & beach views

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed
Cottage rentals with a kayak

Compass Rose Cottage ★ Steps to Flax Pond & Trails

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

Kayaks and Glimpses of Westport Bay

Serenity Views | Waterfront | Kayaks SUP | KingBed

Cape Escape-The Perfect Getaway

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

* Rustic Cape Cod Captain's Quarters Cottage
Other holiday rentals with a kayak

Cozy, Clean, Bikes, Kayaks, Lagoon

Spacious 4-Bedroom home with outdoor dining

Lake Shore Cottage - Private Beach (Waterfront)

ShoestringBayHouse, waterfront & pool in Cotuit

Well appointed, meticulous, 3 bedroom home

Summer/Fall 2025 on the Vineyard!

Stunning 4/2.5 Water View, Hot Tub, Dogs ok

5 minutes walk to Lambert's Cove
Quick stats about holiday rentals with a kayak in Oak Bluffs
Total rentals
30 properties
Nightly prices starting at
£111 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with breakfast Oak Bluffs
- Private suite rentals Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- House rentals Oak Bluffs
- Rentals with beach access Oak Bluffs
- Rentals with lake access Oak Bluffs
- Rentals with a patio Oak Bluffs
- Rentals with a washing machine and dryer Oak Bluffs
- Apartment rentals Oak Bluffs
- Rentals with a fireplace Oak Bluffs
- Boutique hotel rentals Oak Bluffs
- Rentals with an EV charger Oak Bluffs
- Hotel rentals Oak Bluffs
- Waterfront rentals Oak Bluffs
- Family-friendly rentals Oak Bluffs
- Fitness-friendly rentals Oak Bluffs
- Flat rentals Oak Bluffs
- Rentals with outdoor seating Oak Bluffs
- Rentals with a firepit Oak Bluffs
- Rentals with pools Oak Bluffs
- Beachfront rentals Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Rentals with a kayak Dukes County
- Rentals with a kayak Massachusetts
- Rentals with a kayak United States
- Cape Cod
- Mayflower Beach
- Cape Cod National Seashore
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Point Judith Country Club
- Easton Beach
- Oakland Beach
- Coast Guard Beach
- Second Beach
- White Horse Beach
- Horseneck Beach State Reservation
- Chapin Memorial Beach
- Roger Williams Park Zoo
- Lighthouse Beach
- Island Park Beach
- Pinehills Golf Club
- South Shore Beach
- Nauset Beach
- Inman Road Beach
- Goddard Memorial State Park