Beachfront holiday rental in Oriole Beach

4.95 out of 5 average rating, 217 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.

Apartment 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.

4.99 out of 5 average rating, 156 reviews

A bright living area features a spacious white sectional sofa adjacent to a light wood coffee table. Floor-to-ceiling glass doors offer expansive views of the ocean and sky, enhancing the openness of the space. A dining set is visible on the balcony.

Condo in Perdido Key

MELODY OF THE SEA - ON THE BEACH- INCREDIBLE VIEWS

WHAT A VIEW! DIRECTLY ON THE BEACH...GULF SIDE!!! Beautifully remodeled and updated! This retreat has the rare double windows to enjoy stunning panoramic sunset views! On the beach (No roads to cross)! Resort has indoor heated pool & outdoor pool & hot tub overlooking the ocean. 2 fireplaces in the living room bedroom for those cozy mild winters. King size bed in the master... nautical bunkbeds with port holes & queen sleeper sofa in the main living areas. Reserve Your Time Away Today

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.

4.99 out of 5 average rating, 140 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.

Apartment 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+

A private balcony offers sweeping views of the Gulf of Mexico, showcasing the clear blue waters and soft sandy beach below. The horizon merges sky and sea, creating a serene coastal scene. Beach chairs and umbrellas are positioned along the shoreline, inviting relaxation.

4.98 out of 5 average rating, 207 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

**Recently Updated Interior!** Experience the stunning Gulf of Mexico from the comfort of this beachfront 2-King bedroom, 2-bath condo located directly on Pensacola Beach! Nothing separates you from the best white-sand beach on the Gulf Coast. This beach condo boasts a vibrant interior filled with beach-themed accents, a private balcony with sweeping ocean views, and access to 2 pools (1 heated) and a hot tub. Enjoy the best restaurants and shopping on the beach, all within a short walk.

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, 233 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.

A balcony features a round table set for two, including plates and wine glasses. Two white chairs surround the table, overlooking the tranquil blue waters of the gulf and a wooden pier extending into the distance.

4.91 out of 5 average rating, 103 reviews

Best view on the beach! Beach gear included!

Beautiful 1 bedroom, 1.5 bath condo sleeps 6. Bring your swimsuits and get ready to relax! Condo is on 12th floor, tower closest to the pier. - 1 bedroom with king size bed, cozy bunk area for kids, and gel foam mattress on fold-out sofa. (ALL MATRESSES NEW IN SEPTEMBER 2025). - 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

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!~

Popular amenities for Oriole Beach beachfront rentals

Kitchen

Wi-Fi

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

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.

Guesthouse 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

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.

4.97 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.

Guesthouse 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, 152 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 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

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

Townhouse in Navarre Beach

A spacious deck overlooks the calm waters of the Sound, framed by a clear blue sky. Two round, textured outdoor poufs are positioned near the railing, inviting relaxation while enjoying scenic views of the shoreline and distant piers.

4.97 out of 5 average rating, 119 reviews

Waterfront, beach, dock - your Salty Air Retreat!

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, 221 reviews

Navarre Beach Gulf front luxury

4.96 out of 5 average rating, 144 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.

Condo in Perdido Key

Perdido Skye 34 luxury beach vacation rental

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

An aerial view displays the coastline of Navarre Beach, showcasing the vibrant turquoise waters and sandy shores. The location of the townhome is highlighted, surrounded by lush greenery and neighboring properties, with the shoreline and a distant fishing pier visible in the background.

4.96 out of 5 average rating, 94 reviews

Cheerful Island 1BR - Walk to the Beach & Bay

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

5 out of 5 average rating, 42 reviews

A spacious living area is highlighted by a leather sectional sofa adorned with patterned cushions. Two round wooden coffee tables are positioned on a vibrant area rug. Natural light filters through two large windows, complemented by stylish drapes that frame a view of the greenery outside.

Townhouse in Navarre

Super Cozy Townhome w/Pool-close to Navarre Beach

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.

Condo 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, 64 reviews

Waterfront Studio 109 / Ground Floor / Renovated

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.

4.99 out of 5 average rating, 88 reviews

Island Life Beach House! 300ft to water!

A coastal home with a spacious covered front porch is framed by palm trees. Light blue siding complements the white railings. Underneath, a concrete driveway leads to two garage doors. Steps ascend to the porch, inviting guests into the airy interior.

5 out of 5 average rating, 20 reviews

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

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.