Pet-friendly vacation rentals in Historic District, St. Augustine

Guesthouse in St. Augustine

An outdoor seating area features multiple blue Adirondack chairs arranged around a circular stone patio, complemented by a small green table. A lamp post stands nearby, and a flag flutters gently in the breeze, surrounded by lush greenery and tall palm trees.

4.91 out of 5 average rating, 574 reviews

Captain's Quarters Tiny House

Welcome to our newly spacious and private renovated bathroom with our outdoor shower. See photos! This Tiny House has all you need for a cozy, private stay while visiting St. Augustine. The Tiny House sits on 3/4 acres. You will feel the tranquility of this magical property and only 10 minutes to Vilano Beach or the Historic Downtown. The studio is equipped with a sink, toilet, kitchenette, coffee/tea. Commune with nature in your Private Exotic Outdoor Shower, hottub (closed July & August).

Guest suite in St. Augustine

An inviting studio space features a queen size bed with a patterned blanket, surrounded by natural light. A kitchenette area is visible in the background, providing essential amenities. A small seating area with colorful cushions is arranged beside the bed, enhancing the room's functional layout.

4.98 out of 5 average rating, 367 reviews

St. Augustine Studio*Private Entrance & Bath*Bikes

A private studio designed from a garage conversion, located in the up-and-coming West King District. Separate entry with keyless lock welcomes you to this comfortable, clean space with a queen size bed, your own bathroom, kitchenette, and 2 available parking spaces in the driveway. Mini-split AC cools and heats the studio comfortably. High speed internet, flat-screen tv with Netflix for relaxing after a day of sightseeing. Bicycles for exploring our historic downtown less than 2 miles away.

A peaceful fountain surrounded by lush greenery is highlighted in the courtyard. Water cascades gently into a circular basin, where a dog is seen drinking. A stone bench is positioned nearby, partially obscured by vibrant tropical plants.

4.93 out of 5 average rating, 122 reviews

Carriage Hse in the trees, Historic St. Augustine

You have found your cozy oasis tucked under tall shade trees in a private, lush tropical courtyard in the historic district. This convenient and relaxing space is walking distance to everything. It's adorned with 2 covered porches, the Courtyard porch and breakfast porch. Enjoy and relax in the courtyard lit by hundreds of tiny laser lights at night. You will likely see our tortoises roaming the completely fenced property. *Guests must be quiet as sound carries easily to our other 2 studios.

A private balcony overlooks a tranquil backyard, framed by live oak trees. Outdoor seating is provided with a table and chairs, offering a peaceful spot to enjoy nature. The balcony's wooden floor features a simple design, complementing the inviting atmosphere of the space.

4.97 out of 5 average rating, 228 reviews

Tree Top View 2

This spacious tree-top apt overlooks a seldom used and quiet street. The private balcony has a view to majestic live oaks, a home to many squirrels and birds. A perfect place to sip a steaming mug of coffee in the morning or a glass of wine as the sun goes down. This apartment offers a king bed with a separate living area and an equipped kitchen. An easy walk into historic downtown St. Augustine, with it's many delicious eateries and tourist sites. We also rent the adjacent apt Tree Top View 1.

A cozy living room features a rustic brick fireplace and panoramic doors that provide access to the private patio. A stylish table sits in the center, surrounded by comfortable seating. Natural light fills the space, highlighting the home’s character and charm.

4.76 out of 5 average rating, 131 reviews

3 bedroom BLOCKS from old fort, walk everywhere.

The first floor apartment of this turn of the century home accommodates 6 people. With three bedrooms , 1& 1/2 baths and two separate living spaces it’s the perfect space for a family or friends ! Located just blocks from the Old Fort it is walking distance to all things downtown! The main green trolly and Ripleys believe it or not trolly are a few blocks to the south as well …..right next to the fort! If you like quaint, unique spaces with tons of character and old charm this is your place!

4.9 out of 5 average rating, 115 reviews

A modern kitchen is presented with sleek white cabinetry and a striking granite countertop. Stainless steel appliances are neatly arranged, and a large sink is installed in the island. A textured black backsplash complements the overall design, creating a functional cooking space.

Home in St. Augustine

Historic 10 Dupont Lane

Located in the heart of historic downtown St Augustine, Florida. Walk to the sites, restaurants, night life and art galleries. A short 5 minute drive to the Vilano Beach. So much history and charm, entertain the family and friends out back in your zen like garden patio with propane fire pit, couches, dining tables and BBQ, tiki torches. It's really cool. Everything from beds to silverware is new. T.V.'s in every room. The best linens for you and yours. Nespresso Coffee. 2 parking spaces!!

4.95 out of 5 average rating, 184 reviews

Home in St. Augustine

TopRatings•HistoricDowntownCharm•WalkTrolleyAccess

No Cleaning Fee! 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet! Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

Superhost

The exterior of the home is adorned with lush greenery and tropical plants, showcasing a welcoming entrance. The property features a set of stairs leading to a charming front porch, while a manicured lawn enhances the inviting atmosphere.

4.81 out of 5 average rating, 214 reviews

Uptown Classic 1 | Effortless Exploration of STA

Uptown Classic 1 is a 1BD/1BA apartment (2nd floor) that sleeps 2 guests and is located in the heart of St. Augustine. Effortlessly explore the Oldest City with the ease of a 5-min walk to St. George Street - Top sights, local award-winning bars & restaurants surround the home in all directions. The space features cozy, casual interior furnishings and an exterior bistro set. 5-min drive to the beach. Pet-Friendly: Must send message for approval- Pet fee $98 for up to 4 dogs.

Superhost

A small, well-lit bedroom features a spacious bed with a floral patterned comforter. A calming black and white artwork adorns the wall above the bed. Natural light pours in through the window, illuminating the room, which includes a mirror and soft rug on the floor.

Home in St. Augustine

4.77 out of 5 average rating, 159 reviews

Uptown Retreat

Our elegant little Retreat is a small private suite within an updated yet vintage 1890s home. NO SHARED INDOOR SPACE! It free street parking; no parking on property, steps from Uptown eateries & shops, and 3 blocks from the Castillo and "Old Town." This light-filled Queen Suite comes with a mini fridge/freezer, toaster, microwave, coffee/tea, TV w/basic Roku, a small bathroom with a nice sized shower, an antique table for 2 inside the room and a beautiful shared garden!

A well-lit living area features a plush dark recliner and a light-colored sofa, arranged around a small coffee table. A decorative lamp adds warmth beside a window. A TV is positioned on a black stand, while framed artwork and a plant enhance the welcoming space.

4.97 out of 5 average rating, 218 reviews

Dog-friendly, Walk Everywhere apt with FREE BIKES

Come stay in this completely renovated, beautiful second floor, pet-friendly one bedroom apartment with a large fully-equipped eat-in kitchen. A spacious balcony with rocking chairs. Shared use of the fabulous back yard with picnic tables, BBQ grills, and bicycles! One parking space guaranteed. Best part: The location! About a five-minute walk to historic downtown and Flagler. Super comfy queen size 4-post bed. Pet fee is $40 per dog per stay (max of 2 dogs).

Vacation home in St. Augustine

An aerial view captures the charming neighborhood surrounding Hope & Glory, with tree-lined streets and various homes. The picturesque landscape features glimpses of the nearby water and distant landmarks, including the prominent cross, symbolizing the area's historical significance.

5 out of 5 average rating, 132 reviews

Walk Historic Downtown! "Hope & Glory"

Stay one block from Uptown Saint Augustine's shops, eateries & attractions. Enjoy smart TVs, luxury bedding with blackout curtains in bedrooms, screened in porch, back deck, bathing cabana with outdoor shower/clawfoot tub, gas fire pit and Weber grill, game room with darts, fooseball, crafts & More. Cozy, clean & relaxing. Fabulous fully-equipped kitchen, full privacy fence, off-street parking, paved driveway close to downtown and excellent beaches. Prime location!