Holiday rentals with outdoor seating in Santa Rosa Island, Florida

Downtown Intimate Light-Filled Getaway

Explore downtown Pensacola and visit the world-class white sand beaches of Pensacola from this cozy carriage house abode located within walking distance from restaurants, shopping, museums, and nightlife. Stone floors, lots of natural light, and high ceilings. Relax on a private balcony while you sip your morning coffee after a restful night's sleep in a comfy bed with high quality linens. HD TV and a wireless JBL speaker to play your tunes. Full kitchen with everything you need to cook a meal. Ample closet space for all your things and a full size washer & dryer.

Why pay downtown hotel prices?

Friendly, safe downtown location. New & clean 2nd story garage studio apartment with full kitchen & washer/dryer. Five blocks from downtown Pensacola’s main corridor. Palafox Street, restaurants, bars & shopping are a walkable 12 minutes(1/2 mile). Both NAS Pensacola & Pensacola Beach are a 15 min drive. This location offers quick access to festivals, parades, Blue Angel shows, Pensacon & the Blue Wahoo’s Stadium. Rest up for the McGuire’s or Double Bridge runs. Free parking. NO SMOKING!

Redfish Loft, private waterfront Apt. on East Bay

Boat lift available-extra daily fee- 12k lb " pet friendly with fee " loft 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 private grill or visit a local seafood restaurant. Secluded, neighborhood. Join us @ Fire pit ..is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

Never Navarre From Home Cottage

Escape to Florida's best-kept secret, Navarre Beach, just a 5-minute drive from this charming 330 sq. ft. coastal cottage. Perfect for solo travelers or couples, it features airy gabled ceilings, a King-size Murphy bed that converts into a dining/work table, and unforgettable shower experiences!! Conveniently located near restaurants and grocery stores within walking distance, this cozy retreat has everything you need for a relaxing getaway, all just minutes from stunning white sand beaches!!

Tucked Away Tiny

Reconnect with nature at this unforgettable escape. The “Tucked Away Tiny” is a tiny home with HUGE style! It is located in the country woods of Milton, FL on family-owned farm land, but not too far off the beaten path. Only 15 minutes to the heart of the city, and 45 minutes to beaches. It is next door to Sowell Farms which is home to several wedding venues, fenced exotic wildlife (may or may not be seen during your stay), and home of the Trophy for Great American Christmas Light Fight!

Canal-Front Retreat, Walk to Beach, Dock

Waterfront townhome with a private dock and canal-facing decks. Located near Navarre Beach’s white sand shoreline, it offers open water views and fresh coastal breezes throughout the day. • 3 BR | 2.5 BA | Sleeps 9 • Private dock & canal-front decks • Walk to beach • Dedicated workspace • Beach gear included A bright, efficiently arranged layout with comfortable gathering areas and inviting outdoor space, ideal for guests who value scenery, walkability, and a well-kept coastal setting.

Pensacola Pelican Retreat

Beautifully remodeled and updated in the summer of 2017, this vintage 1943, one bedroom, one bath, full kitchen cottage home is located in classic East Pensacola Heights. This 570 sq foot home is located in a safe, family oriented, quiet neighborhood. Its palm tree shaded yard with large deck, gas grill, seating and hammock is conveniently located only minutes to interstate 10, Pensacola's Airport, downtown and beautiful, sugar white beaches and turquoise water.

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.

Bayside Retreat-Panoramic Sunset Views

Bayside Retreat is a renovated 2nd floor one bedroom. Upon entering you'll be greeted by beautiful views of the Sound where the sunsets are unparalleled. This lovely condo includes 3 comfortable beds, King, Day Bed w/Trundle and Queen Sofa Bed, along with a large private balcony and fully equipped kitchen. NOW OFFERING 2 NIGHT DISCOUNTED STAYS MAY THROUGH AUGUST. COMPARE TO LOCAL HOTELS AND SAVE HUNDREDS!!!

The Cedarwood @ Navarre Beach

New house on Navarre Beach! Steps away from the powdery white sand beaches and the crystal clear waters of the Gulf of America. You can relax on your own private deck facing the Santa Rosa Sound while enjoying the extraordinary sunsets. You are just a short walk to amazing shelling, swimming, paddle boarding, kayaking, boogie boarding, or just plain relaxing on the "Most Relaxing Place in Florida."

Eclectic Eco- Friendly Luxe City Cottage

New eco chic cottage features high end touches and appliances in a cozy luxe setting. Sitting on the edge of the downtown jurisdiction, you're never too far away from the action on Palafox Street and a quick jaunt over to the beach. Excellent access to Wahoos Stadium, Sanders Beach, The Oar House, Pensacola Yacht Club, Pensacola Country Club, Joe Patti's, and Pensacola's Naval Air Station.

Tiny Home W/Stock Tank Pool ~15 minutes to Beach

Try out tiny living in this awesome custom tiny home located Pensacola Florida. Tastefully decorated, relaxing space with abundant natural light. Delight in luxurious white marble countertops, beautiful decor & soft velvety linens. No seashell decor in this cottage! Convenient location near downtown Pensacola, Bay Center, East Hill, Hwy & just a short 15 mins to beach!