House holiday rentals in Santa Rosa Island, Florida

The outdoor pool is framed by a screened enclosure, providing clear views of the tranquil bay waters. Comfortable lounge chairs are positioned beside the pool, and potted plants add a touch of greenery. A wooden dock extends into the bay, enhancing the serene ambiance.

4.97 out of 5 average rating, 189 reviews

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.

ValueFamilyDecor

4.95 out of 5 average rating, 294 reviews

A serene bedroom is showcased, featuring a spacious bed with plush bedding. Soft lighting is provided by two bedside lamps. Textured curtains frame the window, and a cozy area rug adds warmth to the space. Additional linens are neatly arranged on a drawer stand.

Home in Pensacola

Charming 2BR Cottage in East Hill near cafes/shops

Relax and unwind in this cozy 2-bedroom cottage nestled in the vibrant, historic East Hill neighborhood. Ideally located, you're just a short stroll away from a dog park, local coffee shops, East Hill Pizza, Publix and Alga Brewery—everything you need for a laid-back day out or an extended stay. Plus, you’re only minutes from all the top attractions in Pensacola. Whether you're here to explore, dine, or just enjoy the local scene, this property is the perfect spot to kick off your adventures.

FamilyValueCondition

4.93 out of 5 average rating, 111 reviews

A newly renovated house is shown with a white exterior and brown shutters. The pathway leads to the front door, surrounded by a well-maintained lawn. Tall trees provide shade in the background, and a wooden fence encloses the backyard.

Home in Pensacola

Peaceful & Fresh Coastal Beulah Getaway

Experience a peaceful and relaxing getaway with your family at this newly renovated cozy home. We are delighted to share it with you whether vacationing or traveling or moving! Enjoy the modern conveniences we have available, including Wifi (no TV), fully equipped kitchen with quartz countertops, and wonderful lighting. Located just 7 minutes off of I-10, and near the Navy Federal Headquarters with a new Publix grocery store (4 min) away. Also just 26 miles (30 min) to the Pensacola Beach!

ValueLocationAccuracy

4.97 out of 5 average rating, 130 reviews

NO PET FEES, fenced yard, 2.5 miles to beach

REST YOUR PAWS in this beach cozy 3 bedroom 2 bathroom home, 1/2 mile to the bay & 2.5 miles to the beach W/ large fenced yard full of mature shade trees. Free high speed internet, board games and books all await you in a quiet neighborhood located close to restaurants, nightlife and pet spa's. It's the perfect place with a forest retreat feeling to unwind with quick & easy access to the beach & downtown. Stocked kitchen with spices for your use. This is a kitchen that you can cook meals in.

FamilyLocationHospitality

4.94 out of 5 average rating, 184 reviews

A spacious living area features a large sectional sofa facing a wall-mounted television above a modern electric fireplace. Light hardwood flooring complements the soft grey walls and blue accent wall. Natural light filters through the window adorned with sheer curtains, enhancing the inviting ambiance.

Home in Gulf Breeze

Stylish Coastal Home | 10min from Pensacola Beach!

Welcome to the Villa ! Modern and newly renovated 2 bed 2 bath (6 guests) Home located in the heart of Gulf Breeze! Centrally located near the beautiful white sands of Pensacola Beach (3 miles) , and shopping of Gulf Breeze. Enjoy a peaceful stay with a private back patio with outdoor seating and lights designed for summer nights. Welcome to our cozy vacation rental featuring brand new kitchen appliances and a fully stocked coffee bar. We look forward to hosting your vacation ! - Sonya

ValueFamilyOutdoor spaces

4.97 out of 5 average rating, 147 reviews

An open living space features a comfortable sofa, complemented by a cozy throw blanket and cushions. Large windows allow natural light to fill the room, which includes a kitchen area with modern appliances. A soft area rug anchors the space, creating a welcoming ambiance.

Home in Milton

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.

LocationFamilyCheck-in

4.95 out of 5 average rating, 244 reviews

The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.

Home in Milton

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.

FamilyValueBarbecue

4.94 out of 5 average rating, 217 reviews

A modern retreat is showcased with a striking dark exterior and large glass windows. The wooden deck is complemented by outdoor seating, while lush greenery surrounds the home, creating a serene setting within the pine forest.

Home in Pace

The Pine House Pace, FL

Enjoy this UNIQUE retreat! 🌲✨ Located on 3 acres of lush pines, this home is the perfect getaway for you or your family. With the romantic modern vibe of the house, you are sure to feel RELAXED, REJUVENATED and ready for whatever is next. Unwind with a book in our 7 ft sitting window, watch the pines sway through the expansive living room windows, or gather with friends for dinner at the outdoor dining area. No matter the reason, the Pine House is for you!

LocationFamilyCheck-in

A three-story beach house is set against a clear blue sky, featuring a light-colored exterior and large windows. Palm trees line the entrance, leading to a stairway that connects to the main door. A private beach area is visible in the background.

4.98 out of 5 average rating, 153 reviews

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!

FamilyValueNearby

A single-story home is shown with a light exterior and a red front door, surrounded by greenery. Two small chairs and a table are positioned on the porch, while a vintage vehicle is parked nearby along the shaded lawn.

4.97 out of 5 average rating, 121 reviews

Endless Summer on Beleza, minutes to beach

Enjoy our home away from home only 2.9 miles from beautiful Navarre Beach (positioned between Destin and Pensacola) and 1 mile from grocery shopping. (also close to restaurants, and Walmart). This newly remodeled 4 bedroom 2 bath home is open and inviting offering great meeting spaces between kitchen, dinning and living room. The large fenced yard offers patio dining and plenty of outdoor entertainment options with the fire pit and propane grill.

LocationValueSleep quality

4.97 out of 5 average rating, 154 reviews

An aerial view highlights the proximity to the beach, with a red marker indicating access. The surrounding area features several beach houses with private pools and a backdrop of high-rise buildings along the coastline. The serene ocean can be seen in the distance under a clear sky.

Home in Orange Beach

Private Pool + Walk to Beach | Orange Beach House

🌴 Just a short walk to the sand, with your own private pool waiting back at the house. This 3BR / 2BA Orange Beach retreat gives you that rare combo of easy beach access + a private pool — no elevators, no crowded decks, just relaxed beach days and space to unwind with your people. Close to Flora-Bama, Adventure Island, and The Wharf when you want to get out, but set up perfectly for easy, laid-back stays. ☀️

LocationFamilyHospitality

A covered deck is presented with hanging hammocks and potted plants, inviting relaxation. Lush green grass surrounds the space, with tall pine trees visible in the background, providing shade and a sense of tranquility. Large windows allow natural light into the interior.