Holiday rentals with a kayak in Santa Rosa Island, Florida

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.

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.

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.

Zen Retreat ON Beach, Golfcart* Hot Tub, SanDestin

8th fl. stylish open studio w/stunning VIEW, beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart with 3+ nts. NEW Pool & Hot Tub. West Elm furniture & King size bed w/ocean view. Sleek Kitchen w/dishwasher & Keurig. WiFi, 55” smart TV. Washer/dryer. Huge balcony to gaze @ the sea. Enjoy the beach, dining, shopping, trails, golf & entertainment all without leaving the resort. Tram pass & Gym. Perfect for honeymoon, baby moon, girls trip, solo travel or lil family vacay *no animals

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!

3102 Stunning 2 Bdrm ~ Heated Pool ~ Book Feb 21st

One of only 14 Exclusive Poolside Villas! Welcome to the Grand Villa Cabana, 1473 sq ft of open concept space, with a walk in/ walk out setup, double sliding doors to bring the outdoors in. This poolside villa cabana sleeps 8 and is the perfect location, with an outdoor dining and patio experience in the tropical gardens alongside the gorgeous lagoon pool. The Grand Villa Cabana has 2 huge bedrooms, 1 King Bed, 1 Queen Bed, Full over Full Bunk Bed and 1 queen sofa sleeper. 5 beds in total.

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+

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.