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Guesthouse holiday rentals in Santa Rosa Island, Florida

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Top-rated Guesthouses in Santa Rosa Island, Florida

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Superhost
A spacious outdoor area features a blue umbrella over a dining table, adjacent to a clear swimming pool. Lush greenery surrounds the pool deck, with views of the tranquil water in the background. The scene is complemented by palm trees and a well-maintained lawn.
Guesthouse in Fort Walton Beach

Private Guest House on the Water | Boat Docks!

You’re invited to enjoy the breathtaking panoramic views as you start your day on our private 2nd floor waterfront deck. This lovely beach house offers 1 queen bd in the bdrm, a twin/full bunk bed, and the sofa in the living room is a pull-out queen bed. Full-size kitchen and dining area. Dock your boat in a private boat slip for a small daily fee. ✔ OMG Views ✯ Waterfront ✯ Private Beach ✯ Entire Place ✯ Boat Slips ✯ Trailer parking ✯ 2 Story Dock ✔ Dog friendly ✔ Full Kitchen ✔ 2 x SmartTV

LocationValueShared spaces

4.83 out of 5 average rating, 205 reviews
Top Guest favourite
A private deck features a turquoise table surrounded by white adirondack chairs and a sofa. The view extends over the landscape, highlighting the gentle waters of the Santa Rosa Sound and clouds drifting across a bright sky.
Guesthouse in Pensacola Beach

S.K.I. BEACH•Walk to Gulf • Sound Views •1BR Suite

Scan QR code for video of property- Cozy Navarre Beach Retreat – Walk to the Gulf Enjoy a peaceful beach escape just a 3 to 5-minute walk to the Gulf of Mexico, with unobstructed views of the Santa Rosa Sound and a comfortable, private space designed for couples or small families. This 1-bedroom suite has earned 5-star reviews for over 5 years and offers the perfect blend of privacy, convenience, and location. Option of one or two private living spaces — perfect for groups traveling together.

LocationValueWi-Fi

4.95 out of 5 average rating, 291 reviews
Top Guest favourite
A modern two-story garage studio apartment is displayed with a clean white exterior. Shaded seating areas are provided by a red shade sail, and large planters filled with greenery are positioned in front. The entrance features decorative outdoor lighting and a wooden gate.
Guesthouse in Downtown Pensacola

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!

LocationValueCheck-in

5.0 out of 5 average rating, 199 reviews
Guest favourite
A comfortable living area showcases a leather couch accompanied by two light-colored armchairs. A ceiling fan provides airflow, while a simple art piece and a small plant add aesthetic interest. Soft lighting illuminates the warm wood flooring, enhancing the open layout.
Guesthouse in Pensacola

Luxury East Hill Apt. Near Downtown Pensacola

Located in Pensacola's historic East Hill neighborhood, our luxury modern apartment is minutes away from the airport, beaches, hospitals, breakfast/coffee shops, restaurants, historic downtown, and shopping! Perfect for business trips, visiting family, budget-friendly beach vacations, or just passing through. W/Dryer, King Bed, Full Kitchen, Gas Fire Pit, and Private Parking. Enjoy your stay in America's first settlement and be sure to check out VisitPensacola.com for events while you're here!

LocationFamilyQuiet

4.98 out of 5 average rating, 191 reviews
Top Guest favourite
A cozy outdoor space is showcased, featuring a patio with a light pink cottage, surrounded by lush greenery. A grill and seating area invite relaxation, with an umbrella providing shade. A small table stands alongside, enhancing the inviting outdoor setting.
Guesthouse in Pensacola

Cozy Garden Cottage

Nestled in private quiet garden behind main house. Off street parking and own entrance. Safe and friendly neighborhood of East Hill. Can walk to a bakery and pub. Between downtown Pensacola and airport. 15 minute drive to beaches. Wireless internet strong signal. T.V. with antenna. Amish "fireplace" heater. Kitchenette with medium refrigerator, sink, microwave, toaster oven, George Foreman grill, griddle designed to cook anything, and eating utensils. Grill on patio. Beach gear.

FamilyValueWalkability

4.9 out of 5 average rating, 356 reviews
Top Guest favourite
The exterior of the coastal cottage is showcased, featuring a welcoming front porch with two chairs and potted plants. A paved pathway leads to the entrance, flanked by a natural landscape of trees and pine needles, creating a peaceful and inviting approach.
Guesthouse in Navarre

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!!

LocationFamilyWalkability

4.98 out of 5 average rating, 128 reviews
Top Guest favourite
A front porch is framed by white columns, providing a welcoming approach to the cottage. Neatly landscaped gardens with various plants and shrubs create a lush atmosphere, while a wooden porch adorned with a small table and chairs invites relaxation and enjoyment of the outdoor setting.
Guesthouse in Milton

Charming Bayou Bungalow near downtown Milton!

Visit historic Milton while staying in our comfortable bungalow, which is close to everything making it easy to plan your visit. Nearby downtown boasts music, festivals, breweries, restaurants and farmers markets. Ride on site bikes on Blackwater Heritage Trail. Explore Marquis Bayou and Blackwater River in on site kayaks. Pick blueberries in season. 40 mins to Navarre Beach. 30 mins to Pensacola. Kitchen w/fridge/micro/toaster oven/dbl burner cooktop. Queen bed with comfy Serta mattress.

LocationValueAccuracy

4.99 out of 5 average rating, 171 reviews
Top Guest favourite
The room features a queen-size bed with striped bedding, a dining table with two chairs, and a full refrigerator. A wall-mounted television is visible, along with a microwave and air conditioning unit. The bathroom is partially visible through an open door.
Guesthouse in Navarre

Southern Wind Guest Cottage

Private guest cottage 100 feet from main house. Very quiet; parking 5 steps to entrance. Queen-size bed with mattress topper, sleeps 2. Full bathroom. Full refrigerator with ice maker, microwave, coffee maker, dining table with 2 chairs, new large screen TV receives 300 channels, WiFi, and Netflix. Heating and Air Conditioning controlled by guests. Keyless entry. Excellent location minutes from beach, 5 minutes from Wal-Mart Supercenter, and a few minutes from restaurants.

LocationFamilyLayout

4.98 out of 5 average rating, 464 reviews
Top Guest favourite
The entrance of the property is marked by a gated driveway, leading to a welcoming guest house surrounded by lush trees. The pathway is bordered by well-maintained landscaping, providing an inviting approach to the home.
Guesthouse in Milton

Siesta Cottage on the Blackwater

Looking for convenience to all of the Gulf Coast's treasures without breaking the bank? Have a boat or jet skis? Coastal guest house on 3 acre waterfront estate on Ward Basin/Blackwater Bay. Close to beaches, downtown Pensacola, and all of the natural wonders of NW FL. Nearby boat ramp, space for boat trailer, and ability to tie up to the dock on site. Sleeps four (queen bed and queen sleeper). No Pets - 2 min to I-10 -20 min to Navarre Beach -30 min to Downtown Pensacola

ValueFamilyKitchen

4.99 out of 5 average rating, 173 reviews
Top Guest favourite
A modern kitchenette features sleek cabinetry and a white countertop. Essential appliances include a refrigerator, a microwave, and an electric kettle. Two wooden stools are positioned at the countertop, and a wall-mounted shelf displays decorative items and kitchenware.
Guesthouse in Pensacola

1950’s East Hill Carriage House

Welcome to our renovated 1950s carriage house, tucked privately behind our home in East Hill. Steps from scenic Bayview Park with paddle boards, canoes, and bikes for rent, and a short ride to bars, breweries, and restaurants on 12th Avenue. Historic downtown Pensacola offers shopping, dining, and live music at Vinyl Music Hall and performances at The Saengar Theater. Plus, the stunning white sands of Pensacola Beach are a short and stunning drive away.

LocationValueAir conditioning

4.97 out of 5 average rating, 220 reviews
Top Guest favourite
A serene canal view showcases calm waters lined with docks and boats. Lush greenery frames the waterway, and buildings are visible in the distance against a clear blue sky. The scene is tranquil, inviting a sense of peace and relaxation.
Guesthouse in Gulf Breeze

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.

FamilyValuePool

4.96 out of 5 average rating, 211 reviews
Top Guest favourite
Guesthouse in Pensacola Beach

The Cedarwood 2 @Navarre Beach.

Newest studio on Navarre Beach. Steps away from the powdery white sand beaches and crystal clear waters. From your room, overlook the Santa Rosa Sound while enjoying the extraordinary sunsets. You are just a short walk to amazing shelling, swimming, paddle boarding, boogie boarding, kayaking , or just plain relaxing at "The Most Relaxing Place in Florida." 2 person maximum occupancy.

ValueLocationWi-Fi

4.98 out of 5 average rating, 158 reviews

Popular amenities for Santa Rosa Island, Florida guesthouses

KitchenWifiPoolFree parking on premisesAir conditioning

Family-Friendly guesthouses

Guest favourite
The exterior of the cottage features a small outdoor seating area with blue chairs and a table surrounded by trees. A decorative fence outlines the yard, complemented by potted plants and seasonal flowers near the entrance. The door is painted blue, adding a pop of color.
Guesthouse in Pensacola

Cottage Under the Trees

ValueFamilyParking

4.91 out of 5 average rating, 696 reviews
Top Guest favourite
Guesthouse in Gulf Breeze

Pool:Relaxing Summer Cottage - Gulf Breeze

LocationValueAmenities

4.99 out of 5 average rating, 117 reviews
Top Guest favourite
The open-concept kitchen features modern stainless steel appliances, including a side-by-side refrigerator and oven. A dining table with a light-colored tablecloth is positioned beside the kitchen, and a comfortable reclining sofa is visible in the living area, creating a welcoming space for relaxation.
Guesthouse in Foley

The Yellow Door

ValueFamilyBarbecue

5.0 out of 5 average rating, 102 reviews
Top Guest favourite
A light blue two-story house is presented from an aerial perspective, featuring a covered balcony with a small red table and chairs. Green trees surround the home, and a paved driveway leads to the entrance, enhancing the inviting exterior.
Guesthouse in Santa Rosa Beach

Carriage House 1.5 bed/1 bath located off 30A

ValueLocationAccuracy

4.88 out of 5 average rating, 237 reviews
Top Guest favourite
A patio area is visible, surrounded by lush greenery and vibrant flowers. A red table and chairs sit under a green umbrella, providing a shaded spot for relaxation. An enormous live oak tree offers additional coverage, enhancing the secluded garden feel.
Guesthouse in Pensacola

North Hill Guesthouse

FamilyLocationBackyard

4.97 out of 5 average rating, 783 reviews
Top Guest favourite
Guesthouse in Pensacola

La Casita: studio near Downtown and NAS

ValueLocationIndoor spaces

4.96 out of 5 average rating, 102 reviews
Top Guest favourite
The exterior of Dune Villa is showcased, featuring a covered porch with a railing and seating for relaxation. Surrounding trees provide shade, while a wooden fence borders the space, offering privacy. The structure's simple design reflects a welcoming ambiance.
Guesthouse in Santa Rosa Beach

Dune Villa - Santa Rosa Beach / 30-A

ValueFamilyLaundry

4.97 out of 5 average rating, 299 reviews
Top Guest favourite
A bright white carriage house and main structure are set against a blue sky. The driveway is lined with gravel, leading to a welcoming porch with a wooden overhang. Surrounding pine trees add a natural element to the serene landscape.
Guesthouse in Santa Rosa Beach

Cypress Key

LocationValueSleep quality

4.98 out of 5 average rating, 132 reviews

Guesthouses with a patio

Top Guest favourite
Guesthouse in Pensacola Beach

Sonoran Mermaid’s Guest Suite

ValueFamilyBathroom

4.88 out of 5 average rating, 165 reviews
Superhost
A modern studio features a light grey sectional sofa facing a television mounted on the wall. Large glass doors lead to a private outdoor area. Blue curtains frame the windows, while decorative mirrors adorn the wall above the sofa, enhancing the overall ambiance.
Guesthouse in Pensacola

Studio 54 - a modern beach-town studio

LocationFamilyKitchen

4.9 out of 5 average rating, 200 reviews
Top Guest favourite
The spacious sleeping area features a large bed with soft bedding, complemented by a neutral-toned blanket. A comfortable couch is positioned nearby, while sliding glass doors provide natural light and access to the outdoor space.
Guesthouse in Pensacola

The Carriageway Cottage -Close to Pensacola Beach!

LocationValueCondition

4.88 out of 5 average rating, 296 reviews
Guest favourite
A cozy living area features a light-colored sofa positioned beside a window. A small coffee table rests on a soft area rug, surrounded by plants and decorative items. Bright light filters through the blinds, illuminating the space softly.
Guesthouse in East Hill

Cozy 1 bedroom East Hill Garage Apartment

ValueFamilyBeach

4.93 out of 5 average rating, 216 reviews
Superhost
The open living space features a modern design with light wood flooring. A comfortable sofa is positioned near large sliding doors that lead to the outdoor area. A dining table with white chairs is set against a backdrop of stylish decor, including a wall-mounted TV.
Guesthouse in Pensacola

Lovely- Pensacola-Guesthouse

ValueFamilyKitchen

4.86 out of 5 average rating, 112 reviews
Top Guest favourite
A private pool area is surrounded by a wooden fence, featuring clear blue water and colorful floats. A shaded seating area with vibrant umbrellas and lounge chairs is visible nearby, offering options for relaxation. The atmosphere is bright and inviting, with a glimpse of the bungalow in the background.
Guesthouse in East Hill

Funky Flamingo~ Guest House~ Pool & Kitchenette

ValueFamilyParks

5.0 out of 5 average rating, 203 reviews
Guest favourite
The exterior of the cottage showcases a welcoming entrance with a decorative wreath adorning the door. A paved driveway leads up to the home, surrounded by well-maintained landscaping featuring shrubs and trees. The backdrop includes a clear blue sky highlighting the peaceful neighborhood.
Guesthouse in Pensacola

Private Guesthouse- 2 mi. downtown & 5 mi. Beach

LocationFamilyWi-Fi

4.97 out of 5 average rating, 225 reviews
Top Guest favourite
Guesthouse in Pensacola

Cozy & Private Guest Cottage - Perfect for Two

FamilyValueCheckout

4.98 out of 5 average rating, 107 reviews

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in East Hill

Cozy Traveller's Cottage Close to Downtown

LocationValueBeach

4.99 out of 5 average rating, 240 reviews
Top Guest favourite
A spacious sleeping area features a king-size bed with a light-colored comforter. Two bedside tables with lamps are positioned on either side. A colorful mural depicting Pensacola, Florida, is featured on the wall above the bed, complemented by a patterned rug beneath.
Guesthouse in Pensacola

East Hill Chillin'

ValueFamilyCheckout

4.97 out of 5 average rating, 235 reviews
Top Guest favourite
The cozy living area features a white sectional sofa and an accent chair, positioned around a light-colored coffee table. Soft natural light filters through multiple windows, creating an inviting space highlighted by a patterned rug and a modern ceiling fan.
Guesthouse in Santa Rosa Beach

"Watercolor-Getaway Bungalow” Beach/6 Pools/Camp

LocationValueLayout

5.0 out of 5 average rating, 218 reviews
Top Guest favourite
A beach bungalow is depicted, elevated on stilts with a wooden staircase leading to a front porch. Blue outdoor chairs are placed on the porch, and lush green grass surrounds the house, complemented by nearby trees. The exterior features light-colored siding and large windows.
Guesthouse in Gulf Shores

House on Little Lagoon

LocationFamilyCheck-in

4.94 out of 5 average rating, 135 reviews
Guest favourite
A welcoming porch is adorned with rocking chairs and decorative cushions, inviting relaxation. Sheer curtains flutter gently in the breeze, framing the view of the lush tropical yard beyond, which features a stone pathway and soft green grass.
Guesthouse in Santa Rosa Beach

Santa Rosa Beach Tiny House

LocationValueLaundry

4.83 out of 5 average rating, 256 reviews
Guest favourite
Two teal Adirondack chairs are placed on a sandy area by the water's edge, facing the calm lagoon. Gentle waves create a serene atmosphere, with green trees visible in the background, framing the tranquil water view.
Guesthouse in Gulf Shores

Cozy Lagoon Cottage

LocationValueGetting around

4.85 out of 5 average rating, 110 reviews
Top Guest favourite
An open layout of the living area and kitchen is displayed, featuring modern appliances and a large flat-screen TV mounted on the wall. A stylish armchair, a decorative coffee table, and large windows allow natural light to fill the space.
Guesthouse in Santa Rosa Beach

Carriage House in Seagrove Close to Beach/Seaside

LocationValueParking

4.98 out of 5 average rating, 110 reviews
Top Guest favourite
A red door with multiple panes is framed by a light-colored wall. A decorative metal sign reading 'WELCOME' hangs above the door, while a small warning sign indicates 'Watch Your Step' near the entrance.
Guesthouse in Downtown Pensacola

The Tropical Hideaway

ValueLocationHospitality

4.98 out of 5 average rating, 129 reviews

Destinations to explore