Tiny house vacation rentals in Santa Rosa County

4.99 out of 5 average rating, 102 reviews

A charming tiny house features a blue exterior and white columns supporting the porch. A welcoming yellow door invites guests, while the surrounding area is landscaped with mulch and small plants. Two chairs are positioned on the porch, offering a spot to relax.

Tiny home in Milton

The Sunset Cottage

Come make memories you won’t forget in our beautiful, romantic tiny house. Watch the sunrise over the fields while sipping a cup of coffee. You will Enjoy exploring the nearby Coldwater Creek during the day, Or if you rather relax on the most beautiful beaches in Florida, it is a short drive. After a busy day, enjoy a magnificent view of the sunset or watch the deer as they approach the fields from the East. Please understand we are still improving the outdoors with additional landscaping.

A cozy outdoor space is showcased, featuring a patio with a light pink cottage, surrounded by lush greenery. A grill and seating area invite relaxation, with an umbrella providing shade. A small table stands alongside, enhancing the inviting outdoor setting.

4.9 out of 5 average rating, 333 reviews

Cozy Garden Cottage

Nestled in private quiet garden behind main house. Off street parking and own entrance. Safe and friendly neighborhood of East Hill. Can walk to a bakery and pub. Between downtown Pensacola and airport. 15 minute drive to beaches. Wireless internet strong signal. T.V. with antenna. Amish "fireplace" heater. Kitchenette with medium refrigerator, sink, microwave, toaster oven, George Foreman grill, griddle designed to cook anything, and eating utensils. Grill on patio. Beach gear.

A private patio area is surrounded by greenery, featuring a wooden deck and a large tree. Natural light filters through the large windows of the apartment. A fire pit is positioned on the deck, creating an inviting outdoor space for relaxation.

4.9 out of 5 average rating, 207 reviews

Private Apartment! Spring Street Retreat

This cozy retreat is a detached private apartment in a quiet neighborhood just minutes from downtown. The space has its own private entrance with a patio, queen bed, Roku TV, Alexa, kitchenette, and a private bathroom. The kitchenette features a mini-fridge, 2-burner stovetop, microwave, toaster, and coffee maker. Whether you are here for a quick weekend getaway, extended vacation, or visiting as a traveling professional, you will find that this space will enhance your Pensacola experience

4.94 out of 5 average rating, 211 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!

4.98 out of 5 average rating, 102 reviews

The exterior of the coastal cottage is showcased, featuring a welcoming front porch with two chairs and potted plants. A paved pathway leads to the entrance, flanked by a natural landscape of trees and pine needles, creating a peaceful and inviting approach.

Guesthouse in Navarre

Never Navarre From Home Cottage

Escape to Florida's best-kept secret, Navarre Beach, just a 5-minute drive from this charming 330 sq. ft. coastal cottage. Perfect for solo travelers or couples, it features airy gabled ceilings, a King-size Murphy bed that converts into a dining/work table, and unforgettable shower experiences!! Conveniently located near restaurants and grocery stores within walking distance, this cozy retreat has everything you need for a relaxing getaway, all just minutes from stunning white sand beaches!!

4.91 out of 5 average rating, 220 reviews

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.

Tiny home in Gulf Breeze

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.

4.91 out of 5 average rating, 116 reviews

A wooden deck extends from the tiny home, featuring two turquoise lounge chairs. A single entrance door is visible, complemented by surrounding greenery in the background, adding a sense of tranquility to the outdoor space.

Tiny home in Milton

Tucked Away Tiny

Reconnect with nature at this unforgettable escape. The “Tucked Away Tiny” is a tiny home with HUGE style! It is located in the country woods of Milton, FL on family-owned farm land, but not too far off the beaten path. Only 15 minutes to the heart of the city, and 45 minutes to beaches. It is next door to Sowell Farms which is home to several wedding venues, fenced exotic wildlife (may or may not be seen during your stay), and home of the Trophy for Great American Christmas Light Fight!

A patio area is visible, surrounded by lush greenery and vibrant flowers. A red table and chairs sit under a green umbrella, providing a shaded spot for relaxation. An enormous live oak tree offers additional coverage, enhancing the secluded garden feel.

4.97 out of 5 average rating, 726 reviews

North Hill Guesthouse

This small but cute guesthouse, repainted and its floors refinished in December 2024, is a five-minute drive from downtown Pensacola, the double A baseball stadium on Pensacola Bay, and a host of restaurants and bars. It is also 20 minutes from Pensacola Beach and the beautiful Gulf Coast. The guesthouse is a separate structure, located in a semi-tropical garden, that affords lots of privacy and quiet in the historical North Hill neighborhood that is ideal for long walks.

4.98 out of 5 average rating, 515 reviews

A vintage cottage features a light blue exterior surrounded by a white picket fence. A gravel driveway leads to the entrance, complemented by tropical landscaping including palm trees.

Cottage in Pensacola

Pensacola Pelican Retreat

Beautifully remodeled and updated in the summer of 2017, this vintage 1943, one bedroom, one bath, full kitchen cottage home is located in classic East Pensacola Heights. This 570 sq foot home is located in a safe, family oriented, quiet neighborhood. Its palm tree shaded yard with large deck, gas grill, seating and hammock is conveniently located only minutes to interstate 10, Pensacola's Airport, downtown and beautiful, sugar white beaches and turquoise water.

The exterior of the cottage features a small outdoor seating area with blue chairs and a table surrounded by trees. A decorative fence outlines the yard, complemented by potted plants and seasonal flowers near the entrance. The door is painted blue, adding a pop of color.

4.91 out of 5 average rating, 654 reviews

Cottage Under the Trees

Quiet, private, secure cottage with kitchen. For sleeping: full bed, twin bed, & sofa (not a sleeper sofa). Will accommodate 3 persons comfortably. Small outside seating area is provided. Few miles from downtown Pensacola. Naval Air Station (NAS), Naval Hospital & Pensacola State College Warrington Campus are within one mile. Fast food is readily available. Walmart is 2 blocks away. Ruby T's, Sonny's BBQ and Waffle House are a few of the nearby restaurants.