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

Redfish Loft, private waterfront Apt. on East Bay
Light airy open floor plan " pet friendly with fee " loft style apartment with private bedroom. Watch the blue herons & dolphins, sit on one of two private decks sipping coffee as you watch the sunrise on the Bay. Paddle the clear waters in our kayaks or bring your SUP. Cook your fresh catch on your private grill or visit a local seafood restaurant. Private, secluded, neighborhood. Join us @ Fire pit ..is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

Bayfront Forest Camper with kayaks/nature trail
The best of both worlds. Our 11-acre waterfront family’s retreat is the ideal getaway for outdoor enthusiasts and beach lovers. With RVs on the front of the property and the occasional tent camper dispersed through out the acreage, you’ll enjoy time away from the crowds walking the mulched trail to the water or using the two kayaks provided for guest use. We offer additional experiences. Outdoor brunch for two/group, afternoon teatime, boho picnic, s’mores bundles, etc. Message with interest.

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!
Well furnished private one bedroom cottage with sunroom, patio, and carport. Full kitchen with bar counter. Has washer/dryer! There's a fenced yard with small deck, perfect for dog owners. The home is situated under shady oak trees with access to waterfront on Santa Rosa Sound. You can enjoy playing with the pooch, swimming, boating, kayaking, fishing, and viewing beautiful sunsets. It's a perfect location for visits to Hurlburt AFB, or vacationers seeking easy access to Ft. Walton and Navarre.

Cozy Bayou Villa - just steps from the water
Are you looking for a comfortable, clean place to relax in an established and desirable area of town while visiting beautiful Pensacola? Then look no further! The Cozy Bayou Villa is located just steps from the water along Bayou Texar and only minutes from the downtown entertainment district and our pristine beaches. Enjoy a morning walk along the waters edge under the oak trees, check out the neighborhood beach and let this location serve as your hub while enjoying all Pensacola has to offer!

Private Guesthouse- 2 mi. downtown & 5 mi. Beach
Tucked away in the highly coveted East Hill area, this cottage has everything Pensacola has to offer. 1/1 on .5 acres. Space includes king bed & futon private driveway parking, courtyard & 2 patios with gas fire pit. Access to common spaces: wood burning fire pit, pergola dining & 2 kayaks! Close to downtown, beaches, shopping & dining. Walking distance to restaurants, coffee shops, & several parks. Whether you are in town for business or here for a vacation you will love this little charmer!

Navy Point Home & game room, near NAS & downtown
*No Pets or children under 10* No Parties $500 fine Bayou Grande Casita is a block from the water with chef's kitchen, lush beds and sofa, & game room w/ ping pong & darts. Take the kayaks to the bayou for a nice paddle where dolphins play. Screened porch for coffee, drinks or a meal outside. Miles of walking paths along the water where we watch the Blue Angels practice. Navy Point has great fishing, a boat ramp, 20 min to beaches, & 10 min to downtown. See our guidebook for local spots.

Charming Bayou Bungalow near downtown Milton!
Visit historic Milton while staying in our comfortable bungalow, which is close to everything making it easy to plan your visit. Nearby downtown boasts music, festivals, breweries, restaurants and farmers markets. Ride on site bikes on Blackwater Heritage Trail. Explore Marquis Bayou and Blackwater River in on site kayaks. Pick blueberries in season. 40 mins to Navarre Beach. 30 mins to Pensacola. Kitchen w/fridge/micro/toaster oven/dbl burner cooktop. Queen bed with comfy Serta mattress.

Serenity on the Bay-Waterfront attached studio
If you're looking for a quiet, get-away directly on the water, and convenient to everything, this is your place! Enjoy beautiful sunrises and gorgeous evening colors in this lovely waterfront studio. You will have a private hot tub steps from your room looking out over the bay. Direct access to a private dock along with two fishing poles and paddle boards upon request. Minutes to historic downtown and 20 minutes to the Gulf of Mexico and Pensacola NAS. this is an adult only property, 21+

Unique water front stay Houseboat Destin/FWB
Seas the Day, center on Ft. Walton Beach,quiet bayou connected to bay and gulf on private 1 acre residence. We are 1 of only 3 HB for 50 miles in area. Paddle boards, kayaks , fishing poles and outdoor fire pit. Car needed to get to white sand beaches (4 miles). Shopping close by. A comfy futon in for a second bed. Boat has AC and heat. Unit is to stay docked.Recently renovated inside and out . Larger deck area with loungers . New lighting and ceiling this past spring! Rare find

Gulf Breeze Your own private resort on the bay!
Best sunset's in Pensacola area. A place where you can watch for dolphins, fish off the dock, pull your boat up, take the kayak out. lay under your own pergola with lounge chair's. Listen to the waves while lying in the hammock watch the pelicans crash land in the bay. grill on the deck . have a picnic. swim off the dock , lay in a raft. Fire Pit , corn hole game in garage,1400 square feet with accommodations for 6. 3 bd/ 2.5 bath 3 mile's to Pensacola beach .

Waterfront with kayaks* Blackwater River Shanty
Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.

Soundside Paradise
Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!
Popular amenities for kayak rentals in Pensacola Beach
House rentals with a kayak

*~Private Waterfront Retreat: Kid & Pet Friendly~*

Exclusive Grand Canal home near Pensacola Beach

Frog Symphony・Sunsets ・ Beachfront・Porch Swing Bed

Kayaking paradise Bring your boat its on the River

Beautiful Cabin On Bon Secour River/Low Fall Rate!

Bayside Bungalow - Full Bayfront House with Pier

Kayak the Bay

🏖Save $ while still being located near everything!
Cottage rentals with a kayak

Waterfront Paradise - Bay Sunsets - Rejuvenate

Hammock Hideaway - waterfront cabin

Waterfront cottage in Fairhope, Alabama

Coastal Country Living

Riverview Retreat/Hot Tub /Golf Cart/Fire Pit

Octopus Cottage

Luxury Beach Cottage With Private Beach

The Cabin on the River
Cabin rentals with a kayak

Riverfront Magnolia Springs Cabin Rental w/ Grill

Riverfront Milton Cabin w/ Boat Ramp & Dock!

Secluded waterfront cabin,boat dock,pier,sunsets

Creekside Fishcamp

Waterfront Pensacola Paradise with Boat Slips!

Blessed
Quick stats about holiday rentals with a kayak in Pensacola Beach

Total holiday rentals
Explore 100 holiday rentals in Pensacola Beach

Nightly prices starting at
Pensacola Beach holiday rentals start at £68 per night before taxes and fees

Verified guest reviews
Over 4,530 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
100 of Pensacola Beach holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pensacola Beach rentals

4.8 Average rating
Pensacola Beach stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Apartment rentals Pensacola Beach
- Private suite rentals Pensacola Beach
- Rentals with a sauna Pensacola Beach
- Rentals with a fireplace Pensacola Beach
- Rentals with breakfast Pensacola Beach
- Waterfront rentals Pensacola Beach
- Rentals with outdoor seating Pensacola Beach
- Family-friendly rentals Pensacola Beach
- Rentals with beach access Pensacola Beach
- Rentals with a washing machine and dryer Pensacola Beach
- Rentals with pools Pensacola Beach
- Villa rentals Pensacola Beach
- Beachfront rentals Pensacola Beach
- Rentals with an EV charger Pensacola Beach
- Flat rentals Pensacola Beach
- Townhouse rentals Pensacola Beach
- Cottage rentals Pensacola Beach
- Fitness-friendly rentals Pensacola Beach
- Pet-friendly rentals Pensacola Beach
- Rentals with a patio Pensacola Beach
- Beach apartment rentals Pensacola Beach
- Guest house rentals Pensacola Beach
- Rentals with a firepit Pensacola Beach
- Rentals with a cinema Pensacola Beach
- Rentals with a hot tub Pensacola Beach
- House rentals Pensacola Beach
- Beach house rentals Pensacola Beach
- Rentals with lake access Pensacola Beach
- Rentals with a kayak Escambia County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Gulf Shores Public Beach
- Destin Harbor Boardwalk
- Crab Island
- OWA Parks & Resort
- Princess Beach
- James Lee Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Gulf State Park
- Perdido Key Beach
- Gulf Shores Shrimp Fest
- Waterville USA/Escape House
- Steelwood Country Club
- Tiger Point Golf Club
- Branyon Beach
- Alabama Point Beach
- Surfside Shores Beach
- Eglin Beach Park
- Raven Golf Club
- Pensacola Beach Crosswalk
- Gulfarium Marine Adventure Park
- Fort Walton Beach Golf Course
- Adventure Island
- Pensacola Dog Beach West