Vacation rentals with a kayak in Santa Rosa Island, Florida

Waterfront cozy condo with king bed & resort pool

Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

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.

Snowbird Discounts! Waterfront Escape-Pet Friendly

Waterfront dream home with incredibly views of Santa Rosa sound. You'll walk in to a fully renovated, private beach house featuring open floor plan where you can spend time with the whole family, enjoying the panorama. Catch the sunrise from the top balcony outside of the master bedroom. Watch for dolphins from your lounge chair on your private beach during the day. Take the kayaks out for paddle in the waves. Enjoy a sunset walk on the private dock. Star gaze from the huge deck in the evening.

Walk to Gulf • Sound Views • 1BR Suite • 2 Decks

Scan QR code for video of property- Cozy Navarre Beach Retreat – Walk to the Gulf Enjoy a peaceful beach escape just a 3 to 5-minute walk to the Gulf of Mexico, with unobstructed views of the Santa Rosa Sound and a comfortable, private space designed for couples or small families. This 1-bedroom suite has earned 5-star reviews for over 5 years and offers the perfect blend of privacy, convenience, and location. Option of one or two private living spaces — perfect for groups traveling together.

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!

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+

Grand Sandestin 4th flr 1 b.room-Steps to Baytowne

Elegant 1BR retreat with 4th-floor views from large balcony, steps from the Village of Baytowne Wharf. Just a 5–10 min TRAM ride to Sandestin pristine private beaches. Features a king bed, queen sofa sleeper, full kitchen, in-unit washer/dryer, and refined décor. Stay connected with high-speed Wi-Fi, unwind with Netflix, and enjoy use of beach chairs and an umbrella stored in our private garage-level storage. Perfect for couples or small families looking to relax and explore Sandestin.

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.

Surf Shack Island Retreat

SNOWBIRD SPECIALS! Welcome to the Surf Shack Island Retreat. This home offers Santa Rosa Island Living, Sound views, short walking distance to pier, beach & sound. Completely remodeled and well equipped three story town home with multiple sleeping arrangements to accommodate groups up to 8. Ideal spot to getaway or space to work remotely, Plenty of space at 2,425 sqft. Private Master, en-suite and sitting balcony. PLEASE DO NOT BOOK IF YOUR GROUP IS LARGER THAN EIGHT

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!