Holiday houses in Santa Rosa Island

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Top-rated holiday rentals in Santa Rosa Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Condo in Navarre

4.91 out of 5 average rating, 101 reviews

Best view on the beach! Beach gear included!

This beautiful 1 bedroom, 1.5 bath condo sleeps 6 and has everything you need for a beach getaway! Bring your swimsuits and get ready to relax! 1 bedroom 1.5 bathroom condo sleeps 6 - on 12th floor - 1 bdrm with king size bed, cozy bunk area for kids, and gel foam mattress on fold-out sofa - All linens and towels provided, including beach towels! - 2 beach chairs, 2 boogie boards and a beach umbrella included - Washer & dryer - Fully equipped kitchen to enjoy dinner with a view - Wi-Fi & cable

Top Guest favourite

Guest suite in Gulf Breeze

4.95 out of 5 average rating, 234 reviews

Upscale Peaceful Suite,Nice NBHD,White Sand Beach!

Looking for a spacious, upscale, peaceful guest suite with private bathroom, shower and small kitchenette near beach, you have found the spot. Easily accommodates three guests with private entry. Has AC,TV, high-speed WiFi, queen bed, sofa bed, small kitchenette, separate restroom, outdoor dinning chairs and table…Good for weekend or more extended stay, free off street parking. Next to Naval Oaks National Seashore with trails outside your door. 10 mins to Pcola Beach, 25 mins to Navarre Beach.

Top Guest favourite

Guest suite in Gulf Breeze

4.9 out of 5 average rating, 105 reviews

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.

Guest favourite

Condo in Fort Walton Beach

4.88 out of 5 average rating, 559 reviews

Cozy Soundside Condo - WataView2!

Vacation or work at our comfortable waterfront kitchenette studio in the heart of Fort Walton Beach. The sugar white sand beaches are just a short drive away, and adventure awaits right at your doorstep on Santa Rosa Sound. Includes pool and marina! Boat slip (28 Ft) available! The unit has a queen bed and futon that lays down to a full size bed. It's very comfortable for small groups. We are real owner-hosts and strive to keep our unit spotless and well supplied for our cherished guests.

Guest favourite

Houseboat in Fort Walton Beach

4.94 out of 5 average rating, 107 reviews

Unique water front stay Houseboat Destin/FWB

Seas the Day, center on Ft. Walton Beach,quiet bayou connected to bay and gulf on private 1 acre residence. We are 1 of only 3 HB for 50 miles in area. Paddle boards, kayaks , fishing poles and outdoor fire pit. Car needed to get to white sand beaches (4 miles). Shopping close by. A comfy futon in for a second bed. Boat has AC and heat. Unit is to stay docked.Recently renovated inside and out . Larger deck area with loungers . New lighting and ceiling this past spring! Rare find

Top Guest favourite

Condo in Fort Walton Beach

4.96 out of 5 average rating, 205 reviews

**Lovely Condo 3 minutes to Beach!!**

Location! Location! Location! Only a three minute drive to the white sand beaches of the emerald coast, and only two minutes to downtown! This cute condo will not disappoint with it's beachy decor. This condo is open and airy with lots of natural lighting. Has balcony seating for those breezy summer nights. Free parking, beach chairs, and a laundry room offered inside unit. We also offer a huge weekly and monthly discount rate. No pets policy. No parties. No smoking inside unit.

Top Guest favourite

Guest suite in Gulf Breeze

4.97 out of 5 average rating, 105 reviews

Coastal King Ste 3.2 mi to Pcola Bch

Bask in the warm sun on soft, white-sandy beaches just minutes drive from your door! 🗺️ Located just off Hwy 98 — the scenic route between Pensacola Beach & downtown 🛏️ Cloud-like King Bed w/memory foam + cooling gel topper 📺 70” Samsung TV w/ Roku 🪑 Comfy Workstation + two recliners w/light massage 🍳 Kitchenette Vibes – full fridge, Keurig, microwave, toaster, & stove w/dishes, pans, & utensils. 🛁 Spa-sized Bathroom – double vanities, enclosed toilet room & Bluetooth fan

Top Guest favourite

Guest suite in Pensacola

4.98 out of 5 average rating, 512 reviews

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.

Top Guest favourite

Guesthouse in Pensacola

4.96 out of 5 average rating, 701 reviews

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.

Top Guest favourite

Home in Milton

4.96 out of 5 average rating, 189 reviews

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.

Guest favourite

Cabin in Gulf Breeze

4.91 out of 5 average rating, 539 reviews

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

Guest favourite

Guesthouse in Pensacola

4.87 out of 5 average rating, 243 reviews

The Carriageway Cottage -Close to Pensacola Beach!

Whether you’re visiting Pensacola for business or pleasure, thank you for your interest in our guest house. We’re located in the heart of East Hill, which is a very charming and established neighborhood. The area is peaceful and quiet, yet only about a 5-10 minute drive downtown Pensacola. We will do everything we can to make your stay great! The guest house is located directly off of our private carriageway behind the house.