Beachfront holiday rentals in Oriole Beach

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Top-rated beachfront rentals in Oriole Beach

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

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Top guest favourite
A panoramic view showcases the pristine white sandy beach meeting the azure waters of the Gulf of Mexico. Beach umbrellas line the shore, while a wooden boardwalk leads through lush greenery, providing access to the beach and inviting relaxation in a serene environment.
Apartment in Santa Rosa Island
4.9 out of 5 average rating, 246 reviews

NAUTILUS 2608, Sleeps 6, Amazing Views!

Amazing views of the Gulf of Mexico from this 2 bedroom 2 bath condo, sleeps 6. On the 6h floor of the beautiful Nautilus condominium, you will enjoy the wide balcony with incredible views. Fully equipped kitchen, all linen and beach towels included. Beach service from March 1st until Oct 31st (2 chairs & an umbrella) Additional beach chairs and umbrellas in the condo. Heated pool. Many restaurants in the area. Groceries 5 min away. Special rates snowbirds and military on TDY. 25 yr old min.

Top guest favourite
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
4.96 out of 5 average rating, 228 reviews

Redfish Loft, private waterfront Apt. on East Bay

Boat lift available-extra daily fee- 12k lb " pet friendly with fee " loft 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 private grill or visit a local seafood restaurant. Secluded, neighborhood. Join us @ Fire pit ..is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

Top guest favourite
A spacious living area is shown, featuring two gray sofas and a sleek television mounted on the wall. Sunlight filters through sliding glass doors, revealing a view of the balcony. A light blue accent chair and a decorative side table complement the setting.
Apartment in Pensacola Beach
4.98 out of 5 average rating, 112 reviews

Waterfront, sleeps 7, walk to everything!

Recently updated 2 bedroom, 2 bathroom 1200 sq ft. large open concept living and dining space and washer/dryer in the unit. Double sliders to the triple size balcony with amazing sunset views over The Little Sabine Bay and The Gulf of Mexico. Centrally located across the street from Casino Beach, The boardwalk, and great restaurants. This is truly one of the best spots on the island with the best of everything including the most amazing views with the convenience of walkability to everything.

Top guest favourite
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.
Apartment in Pensacola Beach
5 out of 5 average rating, 157 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.

Top guest favourite
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.
Apartment in Pensacola Beach
4.93 out of 5 average rating, 255 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.

Top guest favourite
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.
Townhouse in Pensacola Beach
4.96 out of 5 average rating, 145 reviews

Gulfview Townhouse: Beautiful Breeze

Come enjoy our 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

Guest favourite
Apartment in Pensacola Beach
4.92 out of 5 average rating, 148 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 & UMBRELLA SET UP MARCH - OCTOBER!~

Top guest favourite
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.
Apartment in Pensacola Beach
4.95 out of 5 average rating, 174 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

Guest favourite
This aerial view showcases the resort's dual swimming pools surrounded by lounge chairs. The heated pool is visibly larger and features curved edges. Beyond the pools, the white sandy beach and emerald waters of the Gulf are in view, with beach umbrellas lining the shore.
Apartment in Pensacola Beach
4.96 out of 5 average rating, 137 reviews

307 Gulf Front View - Blue Angels ~ Book July 16th

Come experience this Beautiful 5 Star Gulf Front Condo, Heated Gulf Side Pool & Hot tub, This Newly Renovated unit offers a Private, Gulf Front Balcony with Amazing Gulf Views, watch Dolphins, Swim in 2 Gulf Side pools, 1 heated, Hot tub on the Gulf. Sleeps 6, Gulf Front Balcony Master on Gulf, 2 BDRM, 2 BA, Master Suite has a luxurious King Size Cloud Lux Tempur-Pedic Bed. Guest Rm 2 has a Euro Top Plush Queen Mattress, LR has a Memory Foam Queen sleeper sofa.

Top guest favourite
A three-story beach house is set against a clear blue sky, featuring a light-colored exterior and large windows. Palm trees line the entrance, leading to a stairway that connects to the main door. A private beach area is visible in the background.
Home in Pensacola Beach
4.98 out of 5 average rating, 155 reviews

Soundside Paradise

Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!

Top guest favourite
A wooden boardwalk leads through gentle dunes toward the beach, framed by tall grasses. The open sky reflects soft clouds, while the turquoise waves meet the shore in the distance, creating a peaceful connection between the land and sea.
Apartment in Pensacola Beach
4.96 out of 5 average rating, 142 reviews

2/1.5 Seahorse Hideaway Condo

Only a seashell's throw away from the sugar white sands of Pensacola Beach, this is a newly renovated (post 2021 hurricane seasons) seaside getaway. Clean, cozy, and fully furnished we want you to make this your home away from home to get away from the bustle of the world. Unless you like that sort of thing, then, during the summer season, Pensacola Beach Trolley will happily whisk you into the surfing, shopping, and nightlife at the heart of the beach.

Top guest favourite
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
4.99 out of 5 average rating, 111 reviews

Island Life Beach House! 300ft to water!

The entire vibe of this home is "Island Life". If you're looking for a cozy spot on the beach that will make you feel more like you're at home than a tourist on vacation, this is the place for it. Our cute beach house is located on Pensacola Beach, and the water is within sight from the roomy outdoor deck. There are 2 bedrooms and 1 bathroom, kitchen, living space, outdoor space, and everything you need to enjoy life on the beach! FREE PARKING

Popular amenities for beachfront rentals in Oriole Beach

Quick stats about beachfront rentals in Oriole Beach

  • Nightly prices starting at

    Oriole Beach holiday rentals start at £265 per night before taxes and fees

  • Verified guest reviews

    Over 90 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oriole Beach rentals

  • 4.9 Average rating

    Oriole Beach stays are highly rated by guests – averaging 4.9 out of 5!