Holiday rentals in Santa Rosa Island, Florida

La Playa Esmeralda-Panoramic Sunset Views

Welcome to La Playa Esmeralda, a beautifully renovated 2nd floor studio. Upon entering you'll be greeted by beautiful views of the Sound where the sunsets are unparalleled. This lovely condo includes 2 comfortable beds-1 regular and 1 Murphy bed, along with a coffee bar and fully equipped kitchen. You're just a 5 minute walk to the beach. Enjoy a dip in the pool, grilling in the gazebo and fish all night long on our large, private fishing pier, no fishing license required. Early check-in avail.

Sandestin Elation Studio - Baytowne - Golf Cart

Ground-floor studio in Sandestin Golf & Beach Resort with serene golf course and lake views. Steps from Baytowne Wharf’s dining and entertainment. Features a king bed, queen sofa bed, full bath, and kitchenette with microwave and mid-size fridge. Enjoy Wi-Fi, Netflix, resort tram access, and beach gear in garage storage. Optional Golf cart available - inquire about availability and fee. Perfect for a relaxing escape in the heart of Sandestin. And Yes! you may drive the golf cart to the beach.

Cozy private studio suite close to beach.

Your private suite perfectly situated between 2 beautiful beaches (11 miles to Navarre Beach or 13 miles to Pensacola Beach). PLEASE READ DESCRIPTION FULLY BEFORE BOOKING. This suite is the upstairs portion of our home. It is not the entire house. There is a shared front entrance seperated from main living area by a privacy screen. The entire upstairs is yours. The suite consists of a king bed, bathroom and sitting area that includes a microwave, mini refrigerator and keurig coffe maker.

Regency end unit, discounted fall/winter rates!

We've gone to great lengths with extensive recent renovations to make our condo feel like a full 5-star experience - just read the reviews! There are several things that set our unit apart from others, most notably the incredible views in two directions! Add in beach chair service (March through October), along with new appliances and other renovations that are too numerous to list fully, and you have one of the best beach vacation experiences imaginable without spending a small fortune!

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 7 • 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.

Serenity on the Santa Rosa Sound

Serenity on the Sound is the perfect place for your next getaway. Enjoy your private balcony overlooking the Santa Rosa Sound. Bring your water toys (kayak, paddle board or raft) or just a towel to enjoy the sandy white beach just a short walk away from your charming apartment. Full kitchen and bath, private laundry, 1 bedroom with queen size bed, cozy living room and dining. Located minutes from the beautiful white sands of Navarre Beach. Guests must be able to use stairs.

Beautiful, Peaceful East Hill Guesthouse

Beautiful, quiet, relaxing guesthouse (formerly Whitney’s ironwork studio). Private entrance. In historic East Hill, surrounded by peaceful, towering oak and pecan trees. The French doors provide lots of natural light and an open, airy feeling. Private patio. Quiet, historic neighborhood -- perfect for walks or bike rides. Only 1.2 miles from downtown. Within a few blocks are breakfast/coffee shops, restaurants, Publix Grocery, pubs. Easy 15 minute drive to the beach.

Luxe Downtown Studio Apartment

Curated style within walking distance to bars and restaurants downtown, and only a 15 minute drive to Pensacola Beach! This apartment features a a fully equipped kitchen, separate private entrance, fast high speed internet, in unit washer and dryer, a heated bathroom floor, and commercially rated sound proof insulation. The apartment boasts 11ft ceilings, 100%cotton luxury bedding and pillows, rain shower, and a private dedicated parking space just steps from the entrance.

North Hill Guesthouse

This small but cute guesthouse, repainted and its floors refinished in December 2024, is a five-minute drive from downtown Pensacola, the double A baseball stadium on Pensacola Bay, and a host of restaurants and bars. It is also 20 minutes from Pensacola Beach and the beautiful Gulf Coast. The guesthouse is a separate structure, located in a semi-tropical garden, that affords lots of privacy and quiet in the historical North Hill neighborhood that is ideal for long walks.

Cute Carriage House Apartment with View

Situated just east of Pensacola and just north of Pensacola Beach, our place is located in a quiet neighborhood, just a short drive from amazing restaurants and the most beautiful, snow white beaches in Florida. Our private suite has one bedroom, one bathroom and an open living/kitchen area. Sleep up to four guests with a queen bed in the bedroom and a new queen size pull out sofa in the living area.

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.

Oceanfront Paradise - Beach at your backdoor!!

Seamist is a private, 12 unit only condo building with spectacular, oceanfront views both from inside the unit and from the first floor balcony. The stairs down to the pristine white sands and crystal clear waters of the Emerald Coast are just a few feet from the back patio. Seamist is nestled immediately between Seaside Beach & Watercolor Resort and Alys & Rosemary Beach.