House holiday rentals in Milton

A spacious outdoor deck is set with a long table, accommodating multiple guests. Chairs and glassware are arranged neatly for dining. Lush green trees surround the area, offering a relaxed atmosphere, while a glimpse of water can be seen in the distance.

4.88 out of 5 average rating, 252 reviews

Large Mid-Century Home w/Bay View & Ancient Trees

Large nicely furnished 4/4 home located high on a hill overlooking Escambia Bay in Pensacola. This unique home features a large yard & relaxing views of the bay & towering trees, interesting artwork, 2 huge decks, 2 balconies, 70" big screen 4K TV, large open living & huge master suite. Great location short drive from beaches parks & trails. 10 mins from historical downtown, bars and restaurants. 10 mins to Pensacola Airport 25 mins to Pensacola Beach 28 mins to NAS 1 hour to Fort Walton/Destin.

The living area features a light-colored sofa and two armchairs, complemented by decorative pillows. A coffee table is centrally placed, with a woven tray on top. Soft lighting is provided by multiple lamps, and large windows are adorned with sheer curtains, allowing natural light to enter.

4.96 out of 5 average rating, 121 reviews

Midtown Luxury Stay w/Courtyard

Centrally located in Pensacola's thriving shopping district, your home base is minutes away from the airport, beaches, hospitals, breakfast/coffee shops, restaurants, historic downtown, and shopping! Full Kitchen, Washer & Dryer, Gas Grill, Garage, and Private Parking. Perfect for business trips, visiting family, budget-friendly beach vacations, or just passing through. Enjoy your stay in America's first settlement and be sure to check out the VisitPensacola website for events while you're here!

A historic home features a welcoming front porch with multiple seating areas, surrounded by lush greenery. White railings and steps lead to the entrance, while large trees provide shade. The roof is adorned with light fixtures, contributing to the charm of the exterior.

4.82 out of 5 average rating, 130 reviews

Historic Southern Milton Home 30 min from Navarre

Historic 1910 home built by a Judge in Milton 1.5 blocks walk from river board walk & hiking. 30 minutes from Pensacola & Navarre beach. 4 bedroom home with huge porches in front & back with lg trees & Spanish moss for a very secluded feeling. 3 main bedrooms have Queen beds & the 4th room is for children ONLY as it has 2 sets of bunk beds. The main living room has a sofa bed & there is also a cot. A Den & formal dining. Walking distance to splash pad & park with pond, BBQ grill & pavilions.

A spacious backyard is featured, surrounded by a wooden privacy fence. A circular seating area with gravel and fire pit is highlighted, complemented by two hammocks. A well-maintained grassy lawn offers ample space for outdoor activities, while string lights add a warm touch to the evening ambiance.

4.98 out of 5 average rating, 122 reviews

The Lantana Leisure - A Lavish Central Vibe!

Welcome to the Lantana Leisure! This modern duplex embraces a bohemian feel which creates a welcoming space of relaxation and bright engagement. Slow down and decompress in a woven hammock. Laugh with friends and family as you gather around the warm fire or relish the moments of a family cook out. However you choose to spend your time, embrace the uniqueness of this space that had the experience in mind. There are 2 cameras on the exterior of the property that actively record audio and visual.

A charming cottage is set within a lush yard, featuring a welcoming front porch adorned with potted plants. A brick pathway leads to the entrance, framed by vibrant greenery and shaded by mature trees in the background.

4.96 out of 5 average rating, 174 reviews

Walk To Downtown, Fenced Yard, Games, Fire Pit

Welcome to Cooper's Cottage a beautifully renovated 1933 home in the Garden District of Pensacola less than one mile from downtowns historic Seville Square and Palafox St. where you will enjoy bars, restaurants , shopping, art galleries and more. Just 15 min to Pensacola beach and close to NAS home of the Blue Angels. Relax in our fully fenced, pet friendly back yard with gas grill, outdoor dining, lounge seating with fire pit. There are 2 bikes, outdoor games and more. Smart TVs in each room

4.96 out of 5 average rating, 120 reviews

A charming single-story home is surrounded by tall live oak trees, with sunlight filtering through the leaves. A gravel path leads up to the front porch, which features a swing. Windows allow natural light to fill the space, enhancing the serene outdoor setting.

Home in Bagdad

Enjoy The Journey #1 - Near beaches, river & I-10

Your family will be close to everything when you stay at this centrally-located home. This new construction home is perfect for a family vacation or visiting friends. The location is central to beautiful beaches, rivers, culture and only a 3 min drive to I-10. The 3 bed/2 bath home has all the amenities you are looking for plus a cozy outdoor firepit area to enjoy Florida evenings with family and friends. There are beautiful historical homes and great parks and bike paths only minutes away.

4.94 out of 5 average rating, 210 reviews

A modern retreat is showcased with a striking dark exterior and large glass windows. The wooden deck is complemented by outdoor seating, while lush greenery surrounds the home, creating a serene setting within the pine forest.

Home in Pace

The Pine House Pace, FL

Enjoy this UNIQUE retreat! Located on 3 acres of lush pines, this home is the perfect getaway for you or your family. With the romantic modern vibe of the house, you are sure to feel RELAXED, REJUVENATED and ready for whatever is next. Cool the day off in our backyard SITTING POOL, or read a book in our 7 ft SITTING WINDOW. Watch the pines sway through our living room observing windows or have friends over for dinner at our outdoor dining area! No matter the reason, the Pine House is for you!

An open living space features a comfortable sofa, complemented by a cozy throw blanket and cushions. Large windows allow natural light to fill the room, which includes a kitchen area with modern appliances. A soft area rug anchors the space, creating a welcoming ambiance.

4.96 out of 5 average rating, 112 reviews

Blackwater Bay Mae's Cottage

Mae's Cottage is a peaceful little bay house located right off of Interstate 10 in Milton (< 1 mile) and is within steps to the beautiful Blackwater River and Bay. It is approximately 100 yards from water access where you can enjoy fishing, boating, kayaking or just watching the sun set. There is a public boat launch so bring your boat/jet skis/kayaks and fishing gear and head out to the beautiful waters of Blackwater Bay. Relax with the whole family at this peaceful little bungalow.

A single-story brick home is shown, featuring light blue shutters and a welcoming front porch. A well-maintained lawn extends in front, with a driveway leading to a garage on the left. A fence surrounds the backyard, enhancing privacy and space.

4.9 out of 5 average rating, 167 reviews

Large Family Home | Close to Beach

The house has plenty of space for the whole crew to have loads of fun 🏠 You’ll be just a short drive from the beach, and right off the interstate giving you a quick, easy drive into the heart of Pensacola or Whiting Field 🚗 Spacious bedrooms, a patio for coffee-buzzed mornings, a stocked kitchen, and cozy living room are all waiting for you and your group! ☕️ We also have a small breakfast setup to make the mornings easy. 🧇 Enjoy your stay in this beautiful neighborhood!

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.

4.96 out of 5 average rating, 210 reviews

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.

A wooden dock stretches out into calm waters, surrounded by lush greenery. White caps mark the edges, providing a safe boundary. In the background, a spacious home with a dark roof is visible, along with a small boat and kayak nearby.

4.78 out of 5 average rating, 213 reviews

*Waterfront Home w/Boat Dock, & Kayaks!

Read full description before booking! 25-30 minutes to the beach depending on traffic. Bring your boat and dock it in your back yard!! Sit on the porch and enjoy coffee in the morning listening to the birds and frogs nearby. The home is nestled in the quiet community of Escambia Shores. Surrounded by tall pines this relaxing home is perfect for a family vacation or honeymoon. Great fishing in the canal or off the dock! Or Kayak into the bay to fish!

4.97 out of 5 average rating, 140 reviews

An open living area is presented, featuring a light gray sectional sofa and two vibrant yellow chairs. A large wall-mounted TV is visible, surrounded by neutral tones and modern decor. The kitchen bar with high stools is in the background, beneath modern light fixtures.

Home in Navarre

Luxurious, Modernly decorated home Near the beach

Enjoy your stay at Florida’s most relaxing place in this luxurious home specially decorated to create a modern atmosphere, perfectly located halfway between Destin and Pensacola. This beautiful and spacious home is perfect for a family vacation or just a weekend getaway with friends, centrally located to all attractions and necessities and just 1.6 miles from the Gulf of Mexico’s white-sand beaches and turquoise waters.

Popular amenities for Milton house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in East Pensacola Heights

A serene backyard is illuminated at night, featuring a sparkling pool surrounded by a deck and lush greenery. A hot tub, positioned under a wooden pergola, adds to the relaxation area, with soft lighting creating a calm atmosphere. Lounge seating and a dining table are visible nearby.

4.93 out of 5 average rating, 107 reviews

Hot tub/ Pool at this Relaxing Getaway

4.93 out of 5 average rating, 116 reviews

Poolside Family Retreat w/ Hot Tub & Game Room

4.93 out of 5 average rating, 110 reviews

A screened-in pool area features a clear, blue pool surrounded by a spacious deck. Lounge chairs are positioned around the pool for relaxation. Lush palm trees and greenery are visible in the background, offering a glimpse of the outdoor environment.

Home in Pensacola Beach

Fun, sun, sand, and rest. Enjoy your stay with us.

4.97 out of 5 average rating, 174 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 - Sun. Swim. Sunset. Stargaze.

A spacious single-story home features a blend of stone and siding, surrounded by a manicured lawn. The entrance is marked by a wide porch, complemented by large windows and shutters on either side. A driveway leads toward the garage on the left.

4.85 out of 5 average rating, 103 reviews

Pensacola Blue Angel Pool House

Home in Downtown Pensacola

A two-story home features a light blue exterior and a symmetrical design, framed by white columns on the porch. The landscaped front yard is neatly manicured, with low shrubbery and a brick pathway leading to the front door.

4.91 out of 5 average rating, 215 reviews

Historic Downtown Bayfront Home Pool Mins to Beach

4.83 out of 5 average rating, 153 reviews

Home in Perdido Key

Tranquil Seas: Waterfront Unit with Kayaks & More!

A serene backyard space features a clear blue pool surrounded by lush greenery. Sunlight filters through the trees, and a variety of plants decorate the perimeter. Lounge chairs are positioned near the pool, providing a comfortable area to relax and enjoy the outdoors.

4.95 out of 5 average rating, 208 reviews

Flamingo On Fisher In The Heart Of Pensacola

Weekly house rentals

4.8 out of 5 average rating, 30 reviews

A comfortable living room is highlighted by plush seating arrangements and a wooden coffee table. Natural light fills the space, revealing an open layout that connects to a kitchen and dining area. Decorative pillows and a warm color scheme enhance the inviting atmosphere.

Home in Pace

Welcome to Our Home - Pace/Pcola

A comfortable living room area features a gray sectional sofa and a textured rug underfoot. A small side table is positioned next to the sofa. Natural light filters through a large window draped with sheer curtains, illuminating a minimalist décor including a potted plant.

4.97 out of 5 average rating, 39 reviews

Florida Tranquil Retreat

The spacious living area features a large sectional sofa with light-colored cushions, complemented by a round coffee table. A sleek entertainment unit stands against the wall, with a flat-screen TV above. Natural light fills the room through large windows, enhancing the open layout.

5 out of 5 average rating, 14 reviews

Family Time & Tides

A wooden dock extends over calm water, framed by tall grasses on either side. Two turquoise chairs are situated at the end of the dock, offering a serene view of the surrounding landscape and sky dotted with fluffy white clouds.

4.76 out of 5 average rating, 58 reviews

Riverfront House w/ Boat Dock, 3 King Beds

A welcoming living area features a comfortable sofa alongside two ornate red chairs. A wooden coffee table is centrally placed, with a chandelier providing soft lighting above. The dining area is visible in the background, showcasing a dining table surrounded by elegant chairs.

5 out of 5 average rating, 15 reviews

The Downtown Milton House

A comfortable bedroom features a spacious sleigh bed with soft linens and decorative pillows. A knitted throw is casually placed at the foot of the bed. Natural light streams in through a window, and a nightstand holds a lamp beside the bed.

4.9 out of 5 average rating, 49 reviews

Peaceful Cottage on a Shaded Lot

4.92 out of 5 average rating, 36 reviews

A modern kitchen is presented, featuring granite countertops and dark cabinetry. Essential appliances, including a microwave and coffee maker, are visible. A compact bar area with two stools provides additional seating, while natural light enters through the window above the sink.

Home in Pace

Nature's Quiet Embrace

A spacious single-story home is presented in a well-maintained exterior, featuring a textured brick facade. A garage door sits prominently, flanked by simple landscaping that includes green grass and shrubs. The clear blue sky above adds to the welcoming appearance of the property.

5 out of 5 average rating, 75 reviews

30 Minutes to Beaches and Entertainment

Private house rentals

4.99 out of 5 average rating, 89 reviews

The image captures a vibrant sunset over calm waters with streaks of pink and orange illuminating the sky. A wooden dock extends into the distance, and sandy shores are visible in the foreground, creating a serene waterfront atmosphere.

Home in Navarre

Private Waterfront Retreat: Family & Pet Friendly

A spacious living area features a large sectional leather sofa arranged around a decorative area rug. The room is illuminated by a ceiling fan and recessed lighting, while a framed artwork of an animal adds a focal point to the wall.

4.9 out of 5 average rating, 71 reviews

Exotic Farm Stay

A cozy living area is depicted with a green sectional sofa and an accent chair positioned on a patterned rug. A flat-screen television is mounted on a brick feature wall, illuminated by warm lighting. A wooden coffee table holds a few books, enhancing the inviting space.

4.77 out of 5 average rating, 61 reviews

Waterfront Mid-century Revival for Fam & Friends

5 out of 5 average rating, 6 reviews

Peaceful Milton Retreat

A charming home is surrounded by lush greenery, with a circular stone fire pit in the foreground. The house features large windows, offering a light and airy feel. Thick trees provide a natural backdrop, enhancing the tranquil outdoor setting.

4.96 out of 5 average rating, 23 reviews

Little White House off Nine Mile

Home in Downtown Pensacola

A vibrant dining area features a round table surrounded by plush turquoise chairs. The walls showcase eclectic patterns, including floral and geometric designs. A chandelier hangs above, illuminating the space, while a green wall with a neon sign adds a whimsical touch.

4.89 out of 5 average rating, 63 reviews

Good Vibes. Fun Downtown Cottage

4.93 out of 5 average rating, 73 reviews

A private dock extends into the water, illuminated by soft lights beneath a wooden structure. Gentle waves reflect the moonlight, creating a serene atmosphere. The sky shows a mix of clouds and stars, enhancing the tranquil nighttime scene.

Home in Floridatown

Enjoy the bay from the “The Blue Fiddler”