Holiday rentals with a kayak in Pensacola

Jackson Street Retreat - Highly Acclaimed Digs!

This newly renovated, charming 1926 shotgun house is located in the historic Belmont-Devilliers district in downtown Pensacola. The home is a short walk or bike ride to Blue Wahoos stadium, Joe Patti's Seafood, and Palafox Street. The home has every convenience; new HVAC, appliances & fully equipped kitchen with Keurig/coffee, smart TVs, and Wi-Fi. Additionally, the full bath has a standard whirlpool tub/shower and the backyard has a playhouse for the kiddos. Come enjoy your home away from home.

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.

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!

Cozy Bayou Bungalow - 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 Bayou Bungalow 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!

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+

Blackwater Bay Mae's Cottage

Mae's Cottage is a peaceful little bay house located right off of Interstate 10 in Milton (< 1 mile) and is within steps to the beautiful Blackwater River and Bay. It is approximately 100 yards from water access where you can enjoy fishing, boating, kayaking or just watching the sun set. There is a public boat launch so bring your boat/jet skis/kayaks and fishing gear and head out to the beautiful waters of Blackwater Bay. Relax with the whole family at this peaceful little bungalow.

Kayaks & Paddle Boards SunRise & SunSet Views

Welcome to SunnySide UP! The serene 2 bedroom 2.5 bath with water view is located on Little Sabine Bay in Pensacola Beach, FL. Relax on the patio as you look out at the tranquil water as you sip your morning coffee or glass of wine in the evenings. The white sandy beaches of the Gulf of Mexico are right across the street, the nearest public access less than a 5 minute walk! You can also easily walk/drive/trolley to the bustling boardwalk with shopping and plenty of great restaurants.

Waterfront Perdido Beach House w/ Canoes & Kayaks!

Family Friendly | Serene Surroundings | 14 Mi to Tarkiln Bayou Preserve State Park Fresh salty air and Gulf views set the scene at this upscale 5-bed, 4.5-bath vacation rental in Perdido Beach! This restored 1928 home features a wraparound screened porch and cozy bed swings perfect for reading. When you aren't relaxing, take the provided kayak or paddleboard out for a spin just in time for a peaceful sunset. Endless sun-filled adventures await — book your beach oasis today!

Twin Waterfront Home w/Boat Dock & Kayaks!

Read full description before booking! 25-30 min drive to Pensacola beach. 2 bedroom, 2 bathroom, 1400 sq ft townhome near Escambia Bay and Pensacola. Bring your boat and dock it in the back yard!! Sit on the porch and enjoy coffee in the morning listening to the birds and frogs nearby. The home is nestled in the quiet community of Escambia Shores. Surrounded by tall pines this relaxing home is perfect for a family vacation or honeymoon. Wonderful fishing off the dock!

Classic Boatel Yacht

This memorable place is anything but ordinary. Experience a unique getaway aboard our charming 1977 Boatel Yacht, a 47-foot classic docked on a private dock on the Bayou. Perfectly positioned for a serene retreat, the boat offers rustic elegance and craftsmanship, blending modern comfort with timeless style. Enjoy breathtaking views, bird watching and the excitement of watching the Blue Angels practice from the nearby base. Only 15 minute drive to downtown Pensacola.

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!

Tidy Bayou Bungalow

Enjoy beautiful views of the bayou in our carefully cleaned bungalow. Scenic walking/biking path along the bayou right outside your front door! Distances: Downtown 5 mi, Pensacola Beach 14 mi, Perdido Beach 20 mi, Pensacola NAS front gate 1.5 mi, public boat launch 0.2 mi. Fun fact: The Blue Angels home base is Pensacola, and you can see them practicing from our front porch. See photos for copy/paste of the 2022 practice schedule.