Beachfront holiday rentals in Oriole Beach

A bright living area offers views of the Gulf through expansive glass doors. The space features comfortable seating, including wicker chairs and a cozy sofa. A telescope stands nearby for observing the shoreline, while a balcony with seating is visible beyond.

4.99 out of 5 average rating, 136 reviews

Heated Pool + Sunsets | Modern Beach Escape

TWO Gulf-View Balconies | Heated Pool | Gulf & Sound Beach Access | King Primary Suite • Unobstructed Gulf Views from two private balconies • Heated Pool for cool weather swimming • Direct Beach Access – just steps to sugar-white sand • Primary King Suite with spa-like ensuite • Beach Gear Included – chairs, wagon & umbrella • Jacuzzi Tub for ultimate relaxation • Fully Equipped Chef’s Kitchen + Wet Bar with Ice Maker • 65" Smart TV with Sonos Surround Sound • Gated Community with Covered Parki

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.

4.96 out of 5 average rating, 306 reviews

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, 218 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.

4.99 out of 5 average rating, 141 reviews

A tranquil sunset illuminates the sky with shades of orange and purple over a calm bay. Silhouetted dock structures gently reflect on the water's surface, enhancing the serene atmosphere of the waterfront setting.

Flat in Pensacola

Serenity on the Bay-Waterfront attached studio

If you're looking for a quiet, get-away directly on the water, and convenient to everything, this is your place! Enjoy beautiful sunrises and gorgeous evening colors in this lovely waterfront studio. You will have a private hot tub steps from your room looking out over the bay. Direct access to a private dock along with two fishing poles and paddle boards upon request. Minutes to historic downtown and 20 minutes to the Gulf of Mexico and Pensacola NAS. this is an adult only property, 21+

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, 234 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, 159 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.

4.93 out of 5 average rating, 135 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!~

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

The exterior of a two-story beach condo is presented, featuring a light blue façade with white railings. Palm trees flank the entrance, and a gravel pathway leads to the central stairway. The serene landscape and clear blue sky create a tranquil coastal setting.

4.89 out of 5 average rating, 19 reviews

FloraBama Inspired Condo w/ Boat Slip

5 out of 5 average rating, 20 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, 40 reviews

The Pensacola Retreat-Spacious, pet-friendly home

An aerial view captures a modern, three-story white house beside sandy shores. The rooftop deck is highlighted, offering a green space with lounge chairs. Nearby buildings in soft colors enhance the coastal surroundings. Waves roll onto the beach in the background under a clear blue sky.

5 out of 5 average rating, 42 reviews

360 RooftopViews top2bottom Steps 2 Beach Modern

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.

4.96 out of 5 average rating, 133 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

Beachfront home rentals with a pool

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

Heron Nest

Apartment in Orange Beach

A private balcony view overlooks the serene turquoise waters and sandy beach. Two turquoise lounge chairs are positioned on the balcony railing, providing a relaxing spot to take in the scenic landscape of the coastline stretching in both directions.

4.93 out of 5 average rating, 136 reviews

Phoenix X lux beachfront condo next to Florabama!

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.

4.96 out of 5 average rating, 145 reviews

Perdido Skye 34 luxury beach vacation rental

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 scenic view is presented, featuring a vibrant blue sky above a calm waterfront. A pool area is visible, surrounded by sun loungers. Lush palm trees and well-maintained lawns enhance the outdoor space, offering a relaxing atmosphere. Nearby buildings line the waterfront, adding to the picturesque setting.

4.84 out of 5 average rating, 226 reviews

Gorgeous Beach Condo

A vibrant, layered drink is served in a tall glass on a woven tray. The background features a sandy beach and tranquil turquoise waters under a clear blue sky, creating a relaxing coastal setting from the balcony.

4.99 out of 5 average rating, 164 reviews

Beach Front, Low Density Condo in Perdido Key!

Apartment in Orange Beach

A panoramic view of the beach and ocean is presented from the balcony. The water reflects light under a clear sky, while sandy beach stretches along the shoreline. Two bright blue Adirondack chairs are visible by a round table, offering a comfortable seating area for enjoying the surroundings.

4.95 out of 5 average rating, 219 reviews

Beachfront Luxury Condo with Stunning Views

A captivating seascape is displayed at sunset, featuring vibrant orange and pink clouds reflected on the calm water. The sandy beach is framed by dunes and palm trees, with a glimpse of the resort's pool area and wooden walkway leading to the shore.

4.96 out of 5 average rating, 130 reviews

Private beachfront condo, sleeps 8, Perdido Key

Private beachfront home rentals

4.93 out of 5 average rating, 27 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

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.

4.89 out of 5 average rating, 9 reviews

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

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

5 out of 5 average rating, 11 reviews

PrivatePool,SoundViews,Sleeps20

A serene beach view stretches across the horizon, showcasing vibrant shades of blue and green in the water. Soft, sandy beach lies in the foreground, inviting relaxation. The scene reflects a peaceful coastal atmosphere, with minimal presence of people along the shore.

5 out of 5 average rating, 20 reviews

Hot tub-fire pit-2 min walk to beach-NO GUEST FEES

Superhost

A view from the balcony showcases sandy shores leading to the Gulf of Mexico, where the turquoise waters meet a clear blue sky. Sunbathers are positioned on beach towels, while umbrellas dot the shoreline. Grassy dunes are visible in the foreground, with a wooden fence marking the beach access.

4.8 out of 5 average rating, 65 reviews

Sunriser condo at Gulf Winds.

A spacious garage is equipped with kayaks, paddle boards, beach toys, and folding chairs. Items are neatly organized, with kayaks secured on a rack. A comfortable chair is positioned in the corner, providing a convenient spot for relaxing or preparing for outdoor activities.

5 out of 5 average rating, 79 reviews

Kayaks & Paddle boards/Private Patios Water Views

A spacious balcony features a glass-top table surrounded by four high-back chairs, offering panoramic views of the Santa Rosa Sound. The ceiling fan enhances comfort while the inviting blue sky and gentle waves create a serene coastal setting.