Holiday rentals with a kayak in Santa Rosa County

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.

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.

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 or let this location serve as your hub while enjoying all Pensacola has to offer!

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.

Water-Front tiny home.

Come experience true tiny house living while enjoying breathtaking, unobstructed views of the Pensacola Bay and Fort Pickens. You will see no hotels as you sit on the front porch, only nature at its best! Half a mile from a boat launch with public pier, nature trail, dog park, kids park and splash pad. If you’re here on a Tues or Wed you may see the F-18 Super Hornet Blue Angels, as they practice these days. We are 5 minutes to Pensacola Beach and 10 minutes to historic downtown Pensacola.

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 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.

Exclusive Grand Canal home near Pensacola Beach

Exquisite home w/ private dock on the canal - snowbirds welcome! This exquisite three-bedroom Gulf Breeze vacation rental is luxury at its finest with a 25-foot dock and loft! The home is just steps from a lovely canal that feeds into the Santa Rosa Sound along the Gulf of Mexico. This fabulous hideaway is 2 miles from the Naval Life Oaks Reservation (part of the Gulf Islands National Seashore) and 4 miles from fresh seafood, shopping, and nightlife in town!

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!