Beachfront holiday rentals in Oriole Beach

4.96 out of 5 average rating, 303 reviews

A modern dining area features a round table with light-colored tableware, surrounded by four white upholstered chairs. Behind the table, a stylish shelving unit displays decorative items against a marbled wall. Expansive glass doors provide a view of the ocean and allow natural light to flood the space.

Apartment in Perdido Key

Phoenix X 1105- 1BR Florabama Beach Luxury Suite

This meticulously maintained and beautifully furnished Phoenix 10 condo is the epitome of elegance and sophisticated luxury for the discerning couple or small family seeking respite in a beach resort setting. Sip your morning coffee on your private balcony overlooking the beach and Gulf of Mexico. Situated directly on the beach! Parking available in Association lobby for a $60 fee per stay. Linens, towels and complementary starter package (TP/ paper towels, dish detergent and shampoo provided)

4.95 out of 5 average rating, 216 reviews

A peaceful sunset over calm waters creates a vibrant display of orange and purple hues. A wooden dock extends into the water, reflecting the colorful sky, while silhouettes of trees line the distant shore. The scene evokes tranquility and natural beauty.

Flat in Gulf Breeze

Redfish Loft, private waterfront Apt. on East Bay

Light airy open floor plan " pet friendly with fee " loft style apartment with private bedroom. 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 your private grill or visit a local seafood restaurant. Private, secluded, neighborhood. Join us @ Fire pit ..is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

A vibrant welcome sign featuring a flamingo and pineapples is displayed on the door. Inside, a spacious living area includes a white sofa, two black wire chairs adorned with colorful cushions, and a window dressed with sheer curtains, allowing natural light to fill the space.

4.96 out of 5 average rating, 175 reviews

The Flamingo Flat @ Villas on the Gulf

🦩Welcome to the Flamingo Flat! PLEASE READ FULL LISTING. This airy, Palm Beach style condo is the perfect place to relax on a quiet stretch of Pensacola Beach. For great shopping, dining and entertainment you can drive ( less than 3 miles West) to the main hub of P’Cola Beach. Trolley service available during summer months. The beautiful Portofino Island Resort is just 1 mile to the East. MUST BE 25 TO RENT. NO CHILDREN UNDER 12. NO PETS. EARLY CHECK IN MAY BE AVAILABLE FOR AN ADDITIONAL $50.

Townhouse in Pensacola Beach

The exterior of the townhouse is captured, showcasing a bright yellow facade with three balconies. Palm trees are visible in the foreground, and a green lawn is seen at the base of the building. The entrance is located on the lower level, marked by a door.

4.96 out of 5 average rating, 134 reviews

Beautiful Breeze *Newly Built* Gulfview Townhouse

Come enjoy our NEWLY BUILT townhouse located on the gulfside of Pensacola Beach. This 4 br/3 bath, two-story home is steps away from the beautiful sugar white sands. The gulf can be seen from both of the decks. The home is located on the east side of the island in a quiet neighborhood but is only a short trolley/car ride/bike ride away from the boardwalk, restaurants, bars, and shopping. *Please Note* 4 night min May-Aug 2 or 3 night min rest of season Contact owner for possible flexibility

A bright waterfront scene is captured, featuring Little Sabine Bay with reflections shimmering on the water's surface. The view includes marinas with sailboats and yachts, framed by palm trees and gardens, with a pool visible in the foreground.

5 out of 5 average rating, 143 reviews

Stay at Sunshine Daydream on Pensacola Beach

Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

A cozy bedroom features a spacious bed covered in a light blue quilt. Two matching pillows are positioned at the head of the bed. A large window offers views of the surrounding landscape, with a picture of a coastal scene displayed above the bed.

4.94 out of 5 average rating, 161 reviews

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, lighted, private fishing pier, where no fishing license is required.

The open concept living area features a cream-colored sofa and a round coffee table. A wooden loft area is visible in the background, with warm lighting illuminating the kitchen. A large television hangs on the wall, complementing the bright and welcoming space.

4.92 out of 5 average rating, 232 reviews

Amazing Condo on Bay, Steps from Gulf of America

Everything included! Recently remodeled waterfront condo with vaulted ceilings located on Little Sabine Bay and steps from the Gulf of America. Enjoy coffee and cocktails on an amazing balcony overlooking the Bay. Walk or bike to shopping, dining, and the Gulfside. 1 bedroom condo with a loft. The open concept living/kitchen has a 7' island. Beds include King in master, queen in the loft and a queen sofa bed. 1 covered parking spot . 2 bikes 2 Inflatable paddle boards also included.

Townhouse in Navarre Beach

A balcony view is presented, featuring two light blue chairs positioned against a white railing. The landscape includes grass and shrubbery, leading towards a glimpse of water in the distance. Various structures are visible across the water, set against a clear sky.

4.91 out of 5 average rating, 192 reviews

Large Island Townhouse w/ View of Santa Rosa Sound

This 1500 sq. ft. townhouse is home away from home! On an island, it has access to Santa Rosa Sound & is across the street from Gulf of Mexico. Very comfortable w/ 2 bedrooms & 2.5 baths. It has a fully furnished kitchen & 3 balconies. Enjoy water views from main floor & master bedroom. An on-site swimming pool, pier w/ boat slips & beach frontage will meet water recreation needs. Has Direct TV. If you plan to be messy or not clean up after yourself, please don't rent my beach house.

A light-filled living space features a comfortable couch adorned with soft cushions. A coffee table rests on a textured area rug, complemented by a small plant. The adjacent dining area and kitchen can be seen in the background, adding to the open and inviting layout.

4.94 out of 5 average rating, 158 reviews

Pelican's Perch @ Villas on the Gulf

This renovated 2 bed/1.5 bathroom condo is stocked and ready to go--Just bring your groceries and swimsuits! This quaint little beach condo is the perfect, affordable getaway you are looking for. In less than a two-minute walk from the front door, you can have your toes in the sand, soaking up the sun on the Gulf. It features a carport for private parking, two bedrooms, w/ a King bed in one room, two full beds in the other, a couch in the living area, and a queen air mattress.

Superhost

A balcony with a circular table surrounded by four plastic chairs features a view of the bay. The scene includes grassy areas and nearby buildings, with palm trees visible in the background under a partly cloudy sky.

4.8 out of 5 average rating, 128 reviews

Bliss on the Bay 2BR 2BA Beach Condo with Pool D7

Relax with family or friends at our cozy condo with amazing views of the bay and the Gulf of Mexico. You are mere steps from the gulf's famous sugar white sandy beaches. Enjoy the complex's amenities- sun at the private beach, swim in the pool (unheated), grill on the BBQ and chill at the fire pit. Rent bikes and explore the miles of beach paths and the Fort at Pickens. You're a short drive to the core of the beach where there's shopping, restaurants, bars and family activities.

A spacious living room is illuminated by natural light streaming through large windows, offering a view of the Gulf of Mexico. Comfortable sofas are arranged around a central coffee table, while a ceiling fan provides a cooling breeze. A flat-screen television rests on a wooden console.

4.93 out of 5 average rating, 134 reviews

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p

Welcome to The Diving Dolphin... a 2 bedroom/ 2 bathroom condo located in Emerald Isle Condominium complex~ Directly on Pensacola Beach! This beautiful condo is located on the 5th floor and overlooks the stunning waters of the Gulf of Mexico! Come on in and relax- this condo has it all! The condo has a capacity to comfortably sleep 6. We will send you a welcome packet with details about the complex, unit and area! ~COMPLIMENTARY BEACH CHAIR SET UP MARCH - OCTOBER!~

Superhost

A serene waterfront view is presented, with several docks extending into calm waters. Surrounding trees add a natural touch, and various homes line the shore, showcasing their outdoor spaces and inviting atmosphere.

Townhouse in Pensacola Beach

4.92 out of 5 average rating, 146 reviews

Gulf Breeze Your own private resort on the bay!

Best sunset's in Pensacola area. A place where you can watch for dolphins, fish off the dock, pull your boat up, take the kayak out. lay under your own pergola with lounge chair's. Listen to the waves while lying in the hammock watch the pelicans crash land in the bay. grill on the deck . have a picnic. swim off the dock , lay in a raft. Fire Pit , corn hole game in garage,1400 square feet with accommodations for 6. 3 bd/ 2.5 bath 3 mile's to Pensacola beach .

Popular amenities for beachfront rentals in Oriole Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Cottage in Pensacola Beach

The exterior of the house is adorned with a vibrant mural depicting dolphins and coastal scenery, enhancing the tropical atmosphere. Two windows are visible, providing natural light. The entrance area features latticework, and the surrounding ground is covered in gravel and sand.

4.9 out of 5 average rating, 151 reviews

Cozy Mermaid Cottage on Pensacola Beach

4.98 out of 5 average rating, 97 reviews

A panoramic view of the waterfront is visible, showcasing a vast expanse of water under a bright blue sky with scattered clouds. A wooden pier extends into the water, leading towards distant city structures, while grassy land and sandy beach area are framed in the foreground.

Home in Navarre

Navarre|BEACH|Front|Paradise Retreat |Pet Friendly

5 out of 5 average rating, 19 reviews

A well-constructed carriage house features a spacious front porch with black railings and rocking chairs. The overhang creates a shaded area, while the driveway leads to the garage beneath. Lush trees surround the house, complementing the gravel pathway and landscaped areas.

Guest house in Milton

Rainbow Land Carriage House

Home in Downtown Pensacola

A two-story house with a light blue facade is depicted, featuring a covered porch with white railings on the upper level. Lush green grass is present in the front yard, complemented by small shrubs along the pathway. A pebble driveway leads to the entrance.

4.95 out of 5 average rating, 39 reviews

The Pensacola Retreat-Spacious, pet-friendly home

5 out of 5 average rating, 42 reviews

A two-story beach home is prominently featured, set against a backdrop of clear blue skies. Vibrant turquoise outdoor seating surrounds a central fire pit on the sandy ground. The elevated home showcases a spacious deck with steps leading down to the beach area.

Home in Navarre Beach

Beach Therapy on Stunning Navarre Beach ~ Pool

Holiday home in Navarre Beach

A two-story beach house is showcased with a welcoming entrance featuring white steps leading to a covered porch adorned with flowing curtains. Palm trees and lush greenery frame the property, while a garage is visible underneath the home.

4.97 out of 5 average rating, 130 reviews

The Purple Sunset-200ft to Beach w Pool

4.98 out of 5 average rating, 44 reviews

A waterfront property is set against a vibrant sunset, with the water reflecting shades of orange and purple. Lush trees surround the home, and a spacious deck provides views of the serene landscape and boating dock, creating a peaceful atmosphere.

Guest house in Navarre

Beach House Quiet Special Vacation - Pets Welcome

Superhost

A wooden pier extends over calm waters, reflecting soft pastel hues of a sunset sky. A medium-sized dog stands on the pier, looking toward the camera. In the distance, a small boat is moored near a covered dock.

Guest suite in Perdido Key

4.9 out of 5 average rating, 222 reviews

Waterfront Escape to Gulf Beach Getaway!

Beachfront home rentals with a pool

4.99 out of 5 average rating, 151 reviews

A bright living area features a comfortable couch and a chair facing large sliding glass doors, which open to stunning views of the Gulf of Mexico. A circular dining table and four chairs are positioned near a wall-mounted television, creating a welcoming and open space.

Home in Perdido Key

Come stay at Seas~the~Day!! 6th Floor magic!

A wide view of the calm ocean is captured, showcasing gentle waves lapping at the sugar white sands. The horizon displays a gradient of warm colors from oranges to pinks, signaling dawn or dusk. The serene atmosphere offers a sense of tranquility.

4.9 out of 5 average rating, 52 reviews

Herons Nest

The open living and dining area features a rustic wooden table surrounded by black chairs, complemented by a comfortable sectional sofa. Large windows provide unobstructed views of the Gulf, while a ceiling fan and chandelier enhance the space's functionality.

4.99 out of 5 average rating, 220 reviews

Navarre Beach Gulf front luxury

4.96 out of 5 average rating, 143 reviews

The living area features a comfortable sofa in light blue tones and a wooden coffee table. A ceiling fan is positioned overhead. A dining table with four chairs is set near a sliding glass door, which leads to a balcony offering views of the beach.

Apartment in Perdido Key

Perdido Skye 34 luxury beach vacation rental

A private balcony features two turquoise chairs and a small round table, overlooking the emerald green waters and white sandy beach. The expansive view captures the shoreline under a clear blue sky, providing a serene coastal atmosphere.

4.97 out of 5 average rating, 30 reviews

Regency Towers TOP FLOOR Beachfront, pool Pcola

A dining area features a modern table surrounded by six upholstered chairs. The walls are painted in a soothing blue, complemented by artwork depicting coastal scenes. Large sliding glass doors provide a view of the bay, allowing natural light to fill the space.

5 out of 5 average rating, 5 reviews

Sleeps 6-Stunning Bay Front Views-Luxury Resort

A wooden dining set occupies a spacious circular balcony overlooking the beach, featuring four matching chairs and a table. The ocean sparkles in the background, and beach chairs are visible along the shore, creating a serene seaside setting.

4.97 out of 5 average rating, 113 reviews

Poole Paradise: 3 BR beachfront Condo

4.95 out of 5 average rating, 19 reviews

Gone Coastal | Relaxing Bayfront Condo w/ Gulf Acc

Private beachfront home rentals

4.92 out of 5 average rating, 26 reviews

Two blue kayaks are positioned on a grassy area near calm waters, reflecting the soft colors of the sky. The dock is visible in the background, surrounded by trees, creating a peaceful waterfront scene.

Home in Gulf Breeze

Cozy Bay Front | Fire Pit, Kayaks, Sunsets

Villa in Downtown Pensacola

A spacious living area features a light-colored sectional sofa, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, with a view of the outdoors visible. Decorative plants and a wall-mounted television enhance the inviting space.

5 out of 5 average rating, 29 reviews

Seville Sunrise - Amazing Bay View - Downtown

A bright living area features a cozy sofa and a stylish coffee table, with a modern fireplace and a large wall-mounted TV displaying a serene beach scene. Light blue walls enhance the open and airy feel, complemented by a dining area in the background.

4.86 out of 5 average rating, 7 reviews

NEW!Steps to Pcola Beach-Bayview Spacious 3BR/3BA

4.99 out of 5 average rating, 113 reviews

A bright living space features a light-colored sofa paired with modern dining chairs around a table. Large windows frame stunning ocean views, while sheer curtains allow natural light to fill the room. A comfortable chair and a woven accent chair add to the inviting atmosphere.

Apartment in Perdido Key

Beach Front - Peaceful & Private in Perdido Key FL

Two weathered wooden chairs are positioned on a patio, overlooking a vast expanse of green grass that meets the calm waters of the bay. The clear blue sky reflects on the surface of the water, suggesting a serene environment.

4.94 out of 5 average rating, 63 reviews

Waterfront Studio 109 / Ground Floor / Renovated

4.99 out of 5 average rating, 88 reviews

A modern kitchen area features white cabinetry with a spacious island, complemented by bar stools. Large windows allow natural light to fill the space while offering views of the surroundings. Outside, a wooden staircase leads to an elevated entryway, illuminated softly at night.

Home in Pensacola Beach

Island Life Beach House! 300ft to water!

4.95 out of 5 average rating, 94 reviews

The living area features navy blue sofas arranged around a textured coffee table, with light streaming through large sliding doors. Coastal artwork adorns the walls, and a ceiling fan adds to the airy ambiance. The ocean view is prominently visible through the balcony doors.

Flat in Pensacola Beach

Ocean Tranquility. Holiday decorations! Local fest