Family-friendly holiday rentals in Milton

4.89 out of 5 average rating, 278 reviews

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.

Home in Pensacola

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.

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, 148 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.

4.96 out of 5 average rating, 139 reviews

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.

4.99 out of 5 average rating, 170 reviews

A front porch is framed by white columns, providing a welcoming approach to the cottage. Neatly landscaped gardens with various plants and shrubs create a lush atmosphere, while a wooden porch adorned with a small table and chairs invites relaxation and enjoyment of the outdoor setting.

Guest house in Milton

Charming Bayou Bungalow near downtown Milton!

Visit historic Milton while staying in our comfortable bungalow, which is close to everything making it easy to plan your visit. Nearby downtown boasts music, festivals, breweries, restaurants and farmers markets. Ride on site bikes on Blackwater Heritage Trail. Explore Marquis Bayou and Blackwater River in on site kayaks. Pick blueberries in season. 40 mins to Navarre Beach. 30 mins to Pensacola. Kitchen w/fridge/micro/toaster oven/dbl burner cooktop. Queen bed with comfy Serta mattress.

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, 165 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 spacious covered porch features a large dining table surrounded by comfortable chairs, with a view of a serene waterfront. Two ceiling fans create a pleasant breeze, while the green lawn and sitting area with a fire pit are visible in the background.

4.98 out of 5 average rating, 88 reviews

The Bayshore Retreat - lakeside, kayaks, bicycles

Welcome to the Bayshore Retreat! This upscale waterfront oasis features 4 bedrooms & 2-1/2 baths that sleeps up to 16. With a fully stocked kitchen, smart TV in every room, games & puzzles makes this retreat perfect for any occasion. Two patios with a grill, outdoor dining and a fire pit for entertaining. There is also a fenced in yard to enjoy the beautiful Florida sunshine where you can fish, swim, BBQ or just enjoy the amazing sunset views. What are you waiting for? Book today!

The exterior of a garden home is depicted, showcasing a welcoming entrance beneath a covered porch. Potted plants are arranged along the sides, and a small table and seating area are visible. A decorative 'WELCOME' sign is affixed to the door, inviting guests.

4.94 out of 5 average rating, 109 reviews

From our garden house to yours

We think you'll like the recent renovations to our Garden Home... Convenience and comfort for your gulf coast getaway. Situated in a quiet neighborhood of Milton, FL, the Garden Home is located within 10 miles of the Milton Riverwalk and 45 minutes from Navarre beach. Whether you’re visiting for work, to explore the beaches/ bays, and/or to experience the charms of our beautiful Emerald Coast towns, we invite you to choose our Garden Home for your overnight accommodations!

4.99 out of 5 average rating, 173 reviews

The entrance of the property is marked by a gated driveway, leading to a welcoming guest house surrounded by lush trees. The pathway is bordered by well-maintained landscaping, providing an inviting approach to the home.

Guest house in Milton

Siesta Cottage on the Blackwater

Looking for convenience to all of the Gulf Coast's treasures without breaking the bank? Have a boat or jet skis? Coastal guest house on 3 acre waterfront estate on Ward Basin/Blackwater Bay. Close to beaches, downtown Pensacola, and all of the natural wonders of NW FL. Nearby boat ramp, space for boat trailer, and ability to tie up to the dock on site. Sleeps four (queen bed and queen sleeper). No Pets - 2 min to I-10 -20 min to Navarre Beach -30 min to Downtown Pensacola

A kayak glides across calm water, reflecting a vibrant sunset. Pine trees line the shore, framing the scene as hues of orange, pink, and purple fill the sky. Fishing poles are positioned close by, adding to the peaceful setting.

4.86 out of 5 average rating, 150 reviews

Twin Waterfront Home w/Boat Dock & Kayaks!

Read full description before booking! 25-30 min drive to Pensacola beach. 2 bedroom, 2 bathroom, 1400 sq ft townhome near Escambia Bay and Pensacola. Bring your boat and dock it in the 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. Wonderful fishing off the dock!

5.0 out of 5 average rating, 110 reviews

Tropical garden with bar

The perfect Adult retreat. This 2 bedroom 2 full bath home stands out with a tropical style garden, large deck and custom outdoor bar. We are located 3.3 miles from I-10. You can unwind in the European style library, watch a movie on the 65” Smart TV, or enjoy a cold drink at the outdoor bar area. Coffee on the deck in the garden is the best. If you are looking to move to the area, we have an in-house Realtor that can assist you. Not suitable for children under 12.

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.

4.95 out of 5 average rating, 262 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.