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

Private Waterfront Retreat: Family & Pet Friendly
Welcome to your own private waterfront, beach, and retreat destination! Recently renovated, this home is the perfect place to unwind, relax, and soak in the beach life! Tucked away on a dead-end street away from the tourist hustle & bustle. - Panoramic views of the sunset - Private 450ft dock with 2-story deck - Paddle boards/yoga mats - 1 acre of serenity - Complete kitchen - Fenced backyard, outdoor dining, fire pit Location: - 16 mins/10 miles to Navarre Beach - 14 mins/8 miles to grocery

Beach House w/ ALL Gear Included | Walk to Water
This family friendly coastal beach vacation rental located on the “sound side” just footsteps from the sand and water, offers calm waterfront access, a large backyard, and premium included amenities such as paddleboards, kayaks, bikes, cooler, beach chairs, towels, blanket, fishing poles, BBQ grill. Walkable to restaurants, beach bars, food trucks, and park, with Navarre Beach and the longest pier minutes away. Enjoy breathtaking views, sunrises, stunning sunsets, and frequent dolphin sightings.

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.

Cozy Bayou Cottage - 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 Cottage 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!

East Bay Hideaway — A Private Waterfront Escape
Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

Delightful 1-bedroom houseboat with free parking.
Please read listing carefully. No pets allowed and no smoking. This is where your glamping adventures begin. You won’t forget your time at this peaceful and quiet place. Our houseboat is docked on the canal with a beautiful view. We make every effort to provide a safe and fun experience. Some amenities include a shower, bathroom sink, kitchenette, microwave, fridge, A/C and gas grill. Since this is a green houseboat, a porta-potty is located about 50 ft. from the boat and the private parking.

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!

Stay at Sunshine Daydream on Pensacola Beach
Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

Cozy Bayou Home & game room near NAS Dtown Beaches
*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.

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+

Waterfront Paradise "No Wake Zone" On Perdido Key
Welcome to "No Wake Zone Villa" located on Perdido Key, Florida. Beautiful waterfront condo located on the Intracoastal waterway with a semi-private beach. Perdido Key is a coastal community located between Pensacola, Florida and Orange Beach, Alabama. No more than a few hundred yards wide in most places. Perdido Key stretches some 16 miles, with 60% of it located in federal or state parks-making it one of the last remaining unblemished stretches of wilderness on the Gulf of Mexico.

Waterfront Escape to Gulf Beach Getaway!
Waterfront private guest suite with ensuite bedroom including an ultra comfortable king-sized bed. Walk out of your bedroom’s sliding door to a private deck steps away from our beach and pier where you can enjoy swimming, paddle boarding, kayaking or just enjoy the view! You will have your own private full kitchen. Book a massage with our massage therapist before your stay and enjoy your massage just steps away from your suite. Additional bed and bath available as well.
Popular amenities for kayak rentals in Pensacola Beach
House rentals with a kayak

Tidy Bayou Bungalow

Walk/Bike/Golf Cart to Beach | Luxury Home w/Pool

Lagoon waterfront/Private Pier/Fishing/Gulf Views!

Lakefront Home 6 mi from Beach

BAY HOUSE-Private Beach & Sunsets on Pensacola Bay

Cozy Cottage on the Bay - Swim, Fish, Play, Relax

Beach & Lagoon Retreat - Private Beach Access

Vintage Beach Bungalow
Cottage rentals with a kayak

Hammock Hideaway - waterfront cabin

Waterfront cottage in Fairhope, Alabama

Coastal Country Living

Riverview Retreat • Hot Tub • Golf Cart • Fire Pit

Octopus Cottage

Peaceful Waterfront Cottage on Bon Secour Bay

The Cabin on the River

Spanish Moss House on Wolf Bay w/Pier + Boat Slip
Cabin rentals with a kayak

Fish & Relax! Magnolia River Cabin Hideaway

Riverfront Milton Cabin w/ Boat Ramp & Dock!

Secluded waterfront cabin,boat dock,pier,sunsets

Creekside Fishcamp
When is the best time to visit Pensacola Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $228 SGD | $225 SGD | $306 SGD | $272 SGD | $328 SGD | $396 SGD | $429 SGD | $302 SGD | $255 SGD | $255 SGD | $239 SGD | $242 SGD |
| Avg. temp | 12°C | 14°C | 17°C | 20°C | 24°C | 28°C | 29°C | 28°C | 27°C | 22°C | 16°C | 13°C |
Quick stats about holiday rentals with a kayak in Pensacola Beach

Total holiday rentals
Explore 120 holiday rentals in Pensacola Beach

Nightly prices starting at
Pensacola Beach holiday rentals start at $102 SGD per night before taxes and fees

Verified guest reviews
Over 4,840 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
120 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
- Gulf State Park
- Destin Beach
- Gulf Shores Public Beach
- Perdido Key Beach
- Crab Island
- Destin Harbor Boardwalk
- Alabama Point Beach
- OWA Parks & Resort
- Opal Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Village of Baytowne Wharf
- Flora-Bama Lounge
- Gulf Breeze Zoo
- The Hangout
- HarborWalk Village
- Fort Walton Beach Landing
- Henderson Beach State Park
- The Boardwalk on Okaloosa Island
- Waterville USA/Escape House
- The Wharf Amphitheater
- Gulfarium Marine Adventure Park
- Adventure Island
- The Lighthouse Condominiums





