Family-friendly holiday rentals in Oriole Beach

4.95 out of 5 average rating, 221 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.

Guest suite in Pensacola Beach

A tranquil beach scene features soft white sand and gentle waves lapping at the shore. Weathered wooden fence posts stand in scattered alignment, with seagulls resting on top. The vibrant turquoise water meets a clear blue sky, creating a serene coastal atmosphere.

4.94 out of 5 average rating, 256 reviews

Upscale Peaceful Suite,Nice NBHD,White Sand Beach!

Looking for a spacious, upscale, peaceful guest suite with private bathroom, shower and small kitchenette near beach, you have found the spot. Easily accommodates three guests with private entry. Has AC,TV, high-speed WiFi, queen bed, sofa bed, small kitchenette, separate restroom, outdoor dinning chairs and table…Good for weekend or more extended stay, free off street parking. Next to Naval Oaks National Seashore with trails outside your door. 10 mins to Pcola Beach, 25 mins to Navarre Beach.

A welcoming entryway features a decorative round mirror above a console table. A potted plant adds greenery beside the door. A wreath adorns the glass panel of the door, while natural light filters through nearby windows, illuminating the space.

4.87 out of 5 average rating, 170 reviews

Gulf Breeze getaway w/hot tub, minutes to beach

Welcome to your Gulf Breeze getaway! Perfect for a family vacation, this newly furnished bright and cozy home is located in a peaceful neighborhood surrounded by shady trees. This location is a short 9 minute drive to Pensacola Beach! Local convenient stores and restaurants are also minutes from the home. Be sure to include the dreamy white sands and crystal clear waters of Pensacola Beach into your travel plans. You'll also want to soak in the back yard hot tub to relax at the end of the day!

A well-organized living space features a queen bed set against a neutral wall, with a dining table and two chairs positioned nearby. A television is mounted on the wall, and soft lighting is provided by a ceiling fan. The room is complemented by light wood flooring.

4.83 out of 5 average rating, 118 reviews

The Flamingo - Beautiful Studio Apartment

Enjoy a stylish experience at this centrally-located place. Just 8 miles from Pensacola Beach, 20 from Navarre Beach. Close to stores and restaurants. Enjoy the Emerald Coast w/o spending a fortune on hotel. See our other 1BR listing The Pelican with even more space. Queen bed, refrigerator, microwave, kuerig machine w/ complimentary coffee, driveway parking. Unit is part of a lg house with two other units with their own private, exterior entrances. There are no shared spaces and no stairs.

Houseboat in Pensacola Beach

An inviting living space is featured with a comfortable sofa adorned in nautical-themed decor. A steering wheel, integral to the houseboat's design, is visible along with a small table and chairs. Soft natural light filters through light blue curtains, enhancing the ambiance.

4.9 out of 5 average rating, 143 reviews

Delightful 1-bedroom houseboat with free parking.

Please read listing carefully. No pets allowed and no smoking. This is where your glamping adventures begin. You won’t forget your time at this peaceful and quiet place. Our houseboat is docked on the canal with a beautiful view. We make every effort to provide a safe and fun experience. Some amenities include a shower, bathroom sink, kitchenette, microwave, fridge, A/C and gas grill. Since this is a green houseboat, a porta-potty is located about 50 ft. from the boat and the private parking.

A cozy bedroom features a wooden four-poster bed adorned with a patterned quilt in calming tones. Illuminated by natural light from a nearby window, a small bedside lamp provides additional lighting. Art with motivational phrases decorates the walls, enhancing the room's inviting feel.

4.9 out of 5 average rating, 127 reviews

Tom and Nancy's Nut n Fancy

Keep it simple at this peaceful and centrally located home to ALL The beaches! We have internet at 588.1 mbps download and 606.7 upload. NOTHING SLOW HERE! We are central to many Beaches... Pensacola, Navarre , Opal, Fort Walton , Destin, Panama city and many more depending on how far you wish to go. West of us is Orange beach which is in Alabama(40 min) ). Beach Heaven!! Get on the main road (98) 3 blocks from Airbnb and you will ride the coast! Easy Navigation! So Simple and so much to see!

Guest suite in Gulf Breeze

A comfortable sitting area features a navy blue sofa adorned with colorful cushions. A decorative table covered with a light-colored cloth sits in front, complemented by a floral area rug. Natural light filters through the window, dressed with rich maroon curtains.

4.93 out of 5 average rating, 148 reviews

Cozy private studio suite close to beach.

Your private suite perfectly situated between 2 beautiful beaches (11 miles to Navarre Beach or 13 miles to Pensacola Beach). PLEASE READ DESCRIPTION FULLY BEFORE BOOKING. This suite is the upstairs portion of our home. It is not the entire house. There is a shared front entrance seperated from main living area by a privacy screen. The entire upstairs is yours. The suite consists of a king bed, bathroom and sitting area that includes a microwave, mini refrigerator and keurig coffe maker.

4.89 out of 5 average rating, 111 reviews

Low Fall rates, sleeps 8, 2 kings, 12 min to beach

Your family will be close to everything when you stay at this centrally-located Gulf Breeze home. The quiet family friendly neighborhood is the perfect place to relax after a long day at the beach. You will find shopping, Santa Rosa Sound State park, boat launch, bay access, restaurants, day spas, movie theater, Andrew Institute, Gulf Breeze Baptist Hospital, and much more within 5 miles of the home. We are located 10 minutes to Pensacola Beach and a short 28 minute drive to Navarre beach.

Tiny home in Pensacola Beach

A charming tiny house exterior showcases a wooden porch with a handrail and steps leading to a dark front door. Two small windows flank the door, and a potted plant is placed near the entrance. Lush greenery surrounds the structure.

4.91 out of 5 average rating, 222 reviews

Water-Front tiny home.

Come experience true tiny house living while enjoying breathtaking, unobstructed views of the Pensacola Bay and Fort Pickens. You will see no hotels as you sit on the front porch, only nature at its best! Half a mile from a boat launch with public pier, nature trail, dog park, kids park and splash pad. If you’re here on a Tues or Wed you may see the F-18 Super Hornet Blue Angels, as they practice these days. We are 5 minutes to Pensacola Beach and 10 minutes to historic downtown Pensacola.

The living room features two comfortable leather sofas positioned around a central coffee table. A large wall-mounted television displays a cozy bookshelf scene. A neutral-toned area rug covers the floor, and a floor lamp provides soft lighting. Decorative items add a homey touch.

4.88 out of 5 average rating, 127 reviews

Great Gulf Breeze Getaway Near Pensacola Beach

Welcome to Gulf Breeze, Florida! Look forward to a relaxing vacation in this private rental with 3 bedrooms and 2 bathrooms. Relax in your home-away-from-home fully equipped with all your desired amenities. Walk the scenic, sandy beaches of Pensacola, just 15 minutes away. Or, pack your fishing gear and bring home the catch of the day at the many ports and shores that the city of Pensacola boasts. Bring your friends & family to enjoy the Gulf Breeze Getaway!

The cottage is showcased under a clear blue sky, featuring a front porch with white railings and two ceiling fans. Large windows on either side of the entrance allow natural light to fill the rooms. Lush greenery surrounding the home enhances the tranquil setting.

4.99 out of 5 average rating, 126 reviews

The Cottage By The Bay

Beautiful and underneath live oaks and old magnolias, The Cottage was built in October 2015 in a quiet family neighborhood. The decor is "Southern-Coastal". *We live on the property next door. NO water access. The Cottage is located 5 minutes from putting your toes in the bay at Naval Live Oaks. It is 10 minutes from the gorgeous white sands of Pensacola Beach or eating some of the Gulf Coast most delicious seafood.

Camper van/Motorhome in Pensacola Beach

A vintage 16' camper with a light blue exterior sits amidst a lush forest, surrounded by tall trees. A small patio area features a circular table with two chairs and a fire pit, creating an inviting outdoor space for relaxation.

4.9 out of 5 average rating, 175 reviews

Gypsy Rose near the beaches

Reconnect with nature in our very private backyard. Looking for a chill vibe? This is your place. Gypsy Rose is centrally located in Gulf Breeze, FL. Only 6 miles to Pensacola Beach, 10 miles to downtown Pensacola, and 17 miles to Navarre Beach. Gypsy Rose is nestled in a tropical forest setting. Our quiet neighborhood is just minutes to shops, restaurants, parks, the zoo and our beautiful Emerald Coast.

Popular amenities for Oriole Beach family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 217 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

4.97 out of 5 average rating, 177 reviews

A wooden dock extends into calm waters, flanked by two covered structures in the distance. The scene is under a bright blue sky, adorned with fluffy white clouds, creating a serene atmosphere for fishing or relaxation.

Home in Navarre

East Bay Hideaway — A Private Waterfront Escape

Superhost

4.91 out of 5 average rating, 139 reviews

Gulf front @ Emerald Ise, Pensacola Beach~HEATED p

Guest suite in Gulf Breeze

A spacious hot tub is positioned on a stone patio, surrounded by a neatly maintained grassy area. The wooden fence offers privacy, while greenery adds a natural touch to the outdoor setting.

4.9 out of 5 average rating, 227 reviews

East Bay Getaway - Studio with Pool & Hot Tub

A vibrant sunset casts warm hues of orange and gold across the sky, reflecting on the water's surface. The shoreline is framed by gentle waves lapping against the soft, sandy beach. A pier extends into the ocean, while nearby properties provide a coastal backdrop.

4.99 out of 5 average rating, 134 reviews

Beachfront Condo • Pool & Resort Perks

An aerial view of the property reveals a spacious deck with outdoor seating, overlooking sandy terrain and palm trees. The large upper deck includes a dining area and the entrance to a staircase leading to additional outdoor spaces.

4.91 out of 5 average rating, 132 reviews

Hot Tub! Game Room! Balconies Views! Steps 2 Beach

4.96 out of 5 average rating, 213 reviews

A large outdoor pool is surrounded by palm trees and tropical landscaping, offering shaded seating areas under thatched roofs. The pool features a central island with rock formations, and the bright blue water reflects the clear sky above, creating a serene ambiance.

Condo in Perdido Key

This is the one! Perfect Getaway near the beach.

A balcony overlooks the Gulf of Mexico, featuring two red chairs positioned for seaside relaxation. The horizon reflects sunlight, and sandy beach chairs are visible below along the shoreline, creating a serene oceanfront view.

4.93 out of 5 average rating, 152 reviews

Sea-Esta Beach Front 2 Free Chairs, Umbrella, Pool

Family- and pet-friendly home rentals

Townhouse in Pensacola Beach

Aerial view captures a seaside community along a sandy beach, with multiple buildings positioned beside the water. The turquoise ocean contrasts with the white sands, while residential areas and amenities are visible in the background, showcasing the close proximity to the beach.

4.97 out of 5 average rating, 102 reviews

Family Friendly Townhome - Close To The Beach!

An outdoor deck is featured with a spacious dining area, black chairs arranged around a large table, and a built-in grill nearby. Lush plants add greenery, and an area rug provides warmth. Solar panels are visible on the roof, enhancing sustainability.

4.9 out of 5 average rating, 253 reviews

Charming home, 10 min drive to Pensacola Beach

Townhouse in Pensacola Beach

A welcoming living area features comfortable seating arrangements, including a pair of armchairs and a sofa. Natural light fills the space through glass doors leading to a scenic view. A television is mounted above a decorative fireplace, enhancing the relaxed ambiance.

4.81 out of 5 average rating, 266 reviews

CORAL CRAB CONDO-2 Master’s Suites~Pet Friendly

4.97 out of 5 average rating, 154 reviews

The cabin presents a welcoming façade with white siding and dark shutters. A porch with rocking chairs is visible, and an American flag adorns the front. Lush greenery surrounds the property, enhancing its outdoor appeal. Warm sunlight filters through the trees, illuminating the scene.

Cabin in Navarre

Beach Cabin located 3 miles from Navarre Beach

Townhouse in Pensacola Beach

A spacious outdoor terrace is shown, featuring a comfortable seating area with a sectional sofa adorned with colorful cushions. A coffee table sits in front of the seating, with views of the Gulf visible in the background and bright blue skies above.

4.9 out of 5 average rating, 148 reviews

Bay’s Breeze Gulf Front Townhome

Guesthouse in Gulf Breeze

A bright living area features a combination of modern and cozy furnishings. A light gray armchair is paired with a comfortable black couch. A wooden coffee table sits in the center, surrounded by two framed artworks and a large wall clock, creating a welcoming space.

4.95 out of 5 average rating, 133 reviews

Beautiful Get-Away Cottage

Home in East Pensacola Heights

A spacious backyard features a stone fire pit surrounded by a paved area. A porch swing is positioned nearby, complemented by lush green grass and a tall tree. The guest house is set against a backdrop of a wooden privacy fence, creating a peaceful outdoor space.

4.99 out of 5 average rating, 184 reviews

East Pensacola Heights Casita

4.95 out of 5 average rating, 221 reviews

The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.

Home in Milton

Waterfront with kayaks* Blackwater River Shanty

Family-friendly home rentals with a pool

Guest house in Pensacola Beach

A cozy studio apartment showcases a spacious bed against a white brick wall, accentuated by two pendant lights. A gray sofa is positioned nearby, accompanied by a textured throw pillow. A colorful rug adds warmth, while a framed artwork of a cow provides decorative interest.

4.86 out of 5 average rating, 56 reviews

Poolside Cabana

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, 142 reviews

Beachfront Gulf View Oasis

The image features a wooden pier extending into calm waters, leading towards a Bayfront condo complex with yellowish exteriors. Several boats are visible in the water, under a sky adorned with scattered clouds and soft blue hues.

4.92 out of 5 average rating, 120 reviews

Soul Shine - a Water Front Condo

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, 145 reviews

Stay at Sunshine Daydream on Pensacola Beach

Guest house in Pensacola Beach

5 out of 5 average rating, 11 reviews

Gulf Breeze Bungalow

Guest house in Gulf Breeze

4.99 out of 5 average rating, 111 reviews

Spring Break Oasis-Gulf Breeze Hidden Gem

The living area features a leather sofa adorned with colorful cushions, complemented by a glass coffee table. A ceiling fan with leaf-shaped blades hangs above, while large windows are framed by bright yellow curtains. A potted plant adds a touch of greenery to the space.

4.92 out of 5 average rating, 208 reviews

Fun Mid-Century Modern Beachside Condo on the Gulf

An aerial view showcases the townhome situated along the coastline, with the Gulf's waves gently breaking in the background. The neatly arranged buildings reflect a clean layout, while palm trees and a parking area are visible below, highlighting the nearby beach setting.