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.

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. 15min from Pensacola Beach- 20 min to Navarre Beach. 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. East Bay is known for it's Red fish and calm waters.

Tide Together on the Gulf at Beach Colony East

Listing by EXPERIENCED SUPER HOSTS and beautifully professionally decorated 3 B/3 full baths condo RIGHT ON THE GORGEOUS EMERALD COAST WATERS OF THE GULF! Sleeps 8, 1 king bed, 2 queen and a twin XL bunk bed. This 15th floor CORNER UNIT in BEACH COLONY EAST is just what you are waiting for to have panoramic views and enjoy time away with friends or the whole family. INCREDIBLE VIEWS FROM EVERY BEDROOM! (See photos) Olympic size pool, exercise room, walking distance to lots of restaurants.

Cozy Bayou Home & game room near NAS Dtown Beaches

*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.

Coastal Modern Waterfront Escape/RV 50AMP hookup

Welcome to your cozy coastal escape — a beautifully designed 1-bedroom modular retreat perfect for couples, solo travelers. Thoughtfully styled with warm wood tones, modern finishes, vaulted ceilings, and natural light. Enjoy a fully equipped kitchen with open shelving, coffee station, full-size refrigerator, cooktop, microwave, and in-unit washer/dryer. A comfortable sofa and dining space, while the peaceful bedroom features a plush queen bed and calming neutral decor for a restful stay.

Waterfront Haven | King Studio | Hot Tub | UWF I10

Welcome to Mackey Haven! This Superhost designed & managed coastal escape features luxe amenities, stylish décor, beautiful waterfront views, a plush king bed, fully stocked kitchen, and relaxing outdoor spaces. Our peaceful, boutique retreat is perfect for couples or solo travelers. You’ll want to stay for days! ⭐️ Hot Tub / Kayak / Boat Dock ⭐️ Coffee Bar & Breakfast to go ⭐️ Organic Cotton Bed Sheets ⭐️ 75” Roku TV & Fast WiFi ⭐️ Massaging Waterfall Shower ⭐️ Easy UWF & Freeway Acces

Navarre Vacation Escape

Tucked away in a quiet neighborhood less than 600 feet from Santa Rosa Sound and just minutes from the sugar-white sands of Navarre Beach, this clean, bright 3 bedroom, 3 bath getaway is your new happy place. This home comfortably sleeps up to 8 with plenty of room to spread out, kick back, and settle into vacation mode. Inside, you’ll find lots of natural light and thoughtful touches that make this house feel like a warm hug. Come see why Navarre is Florida’s best-kept secret!

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!

Island Life Beach House! 300ft to water!

The entire vibe of this home is "Island Life". If you're looking for a cozy spot on the beach that will make you feel more like you're at home than a tourist on vacation, this is the place for it. Our cute beach house is located on Pensacola Beach, and the water is within sight from the roomy outdoor deck. There are 2 bedrooms and 1 bathroom, kitchen, living space, outdoor space, and everything you need to enjoy life on the beach! FREE PARKING

The Backyard Cottage

Escape to our cozy, one-of-a kind rustic cottage at the Gulf of Mexico! Centrally located, we are just 6 miles from Pensacola Beach, 17 miles from Navarre Beach, and 10 miles from Downtown Pensacola. We offer a quiet, chill environment while being just minutes from shops, restaurants, beaches, nature trails and the zoo. The Backyard Cottage is lovingly placed in our shared yard, so please be respectful of our space that we have chosen to share.

Waterfront tiny Cabin/ Glamping

Quaint waterfront cabin! Peaceful surroundings, shady oak trees, hammock, boat launch, beautiful dock for enjoying the sunrise. Cabin has a loft with Japanese bed, Murphy bed, and futon. Bathroom has a toilet and shower. simple kitchenette with toaster oven, burner, sink, microwave, full fridge, and dishes. Television has DVD player no cable!, no WiFi!. Small dinette table w/4 chairs. A/C; NO PARITIES ALLOWED! Sleeps 4 comfortably