Guesthouse holiday rentals in St. Johns County

A pool area is showcased with a clear blue pool surrounded by a stone patio. Two lounge chairs are positioned on one side, complemented by a thatched umbrella. A covered seating area can be seen in the background, adding to the inviting ambiance of the outdoor space.

4.99 out of 5 average rating, 216 reviews

Historic St. Augustine 2/1 Cottage & Pool

About this space: Welcome to this poolside cottage located in Historic St. Augustine. This cottage is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This cottage has 2 bedrooms and 1 full bathroom, living room, kitchen and direct access to the pool. This space: This is a detached cottage located behind the main house Guest access: Keyless code entry Other things to note: Please keep in mind that the pool is a shared space :)

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4.91 out of 5 average rating, 369 reviews

10 Minutes to EVERYTHING!! Modern Serene Studio

Serene Studio is just that- a quiet, peaceful, private space to lay your head after exploring St. Augustine. Our 500 sq. foot studio cottage is detached from the main house, where we live. It's set in a residential neighborhood that runs along the Intracoastal Waterway (which makes for gorgeous morning or evening strolls). We're a 10 minute car ride (without traffic!!) to the historic downtown or St. Augustine Beach. Serene Studio is the best of both worlds without the noise, hustle and bustle!

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4.88 out of 5 average rating, 186 reviews

Island’s Edge Guest Cottage on Anastasia Island.

Professionally cleaned marsh front private cottage with amazing views. Nestled between the state park, our famous AMP, great beaches & downtown. Your deck is perfect for a bbq, bird watching & sunset cocktails. ☹️Sorry no marsh access.☹️ Please Note: this is a space where the main house is visible from the cottage. We do have a small dog that will be contained for the entirety of stay. Park trails and beach are close by. Stroll over to the Saturday morning market at “the Amp”. You’ll love it.

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A spacious studio features a king-sized bed with a soft green coverlet and a cozy dark sectional sofa. Natural light enters through windows, highlighting the modern kitchen area and dining space in the background. A bathroom door is visible on the right side.

4.95 out of 5 average rating, 175 reviews

Historic Downtown Studio

Experience the charm and elegance of historic St. Augustine, Fl in our quaint carriage house. Located with in walking distance of many iconic landmarks, such as Flagler College, and the San Sebastián winery. Immerse yourself in the city culture, unique shops and dining scene. Whether you're seeking a romantic getaway or a cozy solo retreat, our carriage house offers a blend of comfort and convenience. Book your stay with us and experience the charm of this historic destination like a local.

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Guesthouse in Butler Beach

A sunset scene features warm colors of orange and yellow spreading across the sky, reflecting on a calm body of water. Silhouettes of a pier and surrounding foliage create a serene waterfront atmosphere.

4.84 out of 5 average rating, 100 reviews

Sea & Serenity

Waterfront 3 Bedrooms and 2 New Bathrooms, new kitchen, 4 large TV's, 1 King & 3 Queen size beds with so many custom features! From the moment you open the door to this cottage you will know what a real vacation is all about. If you want to Jet Ski, Kayak, Fishing, Golf, Tennis, Boating, just relaxing on the beach or grab a book and sit on the dock and watch the boats while catching the sunset. We are located on Anastasia Island close to Historical Downtown, The AMP, Beach and so much more!

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4.94 out of 5 average rating, 459 reviews

The Garden Casita in St. Augustine Florida

Secluded garden casita tucked away three tenths of a mile from the city gates. Take the private garden pathway to serenity's doorstep, and gain access to WIFI, free parking, and a kitchenette equipped with the basic necessities. The zen garden serves as a wonderful resting space to relax and unwind from your day. The casita features a queen size bed with luxury linens, desk nook and a full bathroom. Come find your peace at the Garden Casita on the grounds of a 100 year old private home.

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Superhost

The exterior of the two-story cottage showcases a combination of stone and stucco walls, framed by wooden shutters. A large tree provides shade in the foreground, and a welcoming pathway leads to the entrance, enhancing the home's charming architectural features.

Guesthouse in Lincolnville

4.94 out of 5 average rating, 508 reviews

Storybook Cottage-Historic Downtown St. Augustine

Welcome to Storybook Cottage on Lake Maria Sanchez in Historic Lincolnville, a scenic 8-10 minute walk from the heart of Downtown St. Augustine. Enjoy this beautiful two story, 2 BR/ 1.5 BA newly renovated cottage complete w a spacious family room and kitchen. Relax and enjoy your morning coffee or evening cocktails from the comfort of the balcony or the property's cozy courtyard. Perfect for a family trip or a romantic getaway to enjoy all that the Nation's oldest city has to offer.

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Guesthouse in Southeast Jacksonville

The kitchen features white cabinetry with ample storage and a spacious countertop. Stainless steel appliances, including a double oven and dishwasher, are visible. A window allows natural light to illuminate the workspace, and a small area rug adds a touch of warmth.

4.98 out of 5 average rating, 402 reviews

Private Apartment

Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen. Property access for our guests only. Complimentary beer, sodas, water and coffee! Adults only.

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Guesthouse in Palm Valley

A spacious swimming pool is enclosed by a screened structure, offering privacy and shade. Two umbrellas provide shelter over lounge chairs for relaxation. The backdrop features a porch with seating, surrounded by lush greenery that enhances the serene atmosphere.

4.91 out of 5 average rating, 103 reviews

Palm Valley Pool House

Airbnb has made host(s) hide Airbnb fees in the host’s price- that is why advertised price has increased! Airbnb takes over 15%. Only rented out for certain weekends to guests with reviews. (2 people max.) Your little haven will have a screened pool enclosure attached to the pool house’s private porch. During rental times, the pool area is private for you, neighbors aren’t able to see as well. Sorry, this place is not for gatherings, -of any kind. Absolutely no children.

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Guesthouse in East Palatka

The rustic boathouse is positioned near a scenic wooden dock extending into the river. Sunlight reflects off the water while a peaceful horse stands nearby, surrounded by lush greenery. The weathered exterior of the boathouse complements the natural setting.

4.95 out of 5 average rating, 132 reviews

Charming Rustic Boathouse

Come stay at our rustic boathouse along the serene river. Its weathered, wooden, exterior exudes charm, adorned with unique decor. The sunlight reflects the water, casting shimmering light against the boathouse. Surrounding it, is lush greenery and trees that create a picturesque backdrop. Inside the boathouse is a cozy and inviting, with simple furnishings and the gentle scent of wood. It's a haven where one can escape the bustle of everyday life and embrace the countryside.

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4.98 out of 5 average rating, 157 reviews

Guesthouse in Mandarin

Pet Friendly Studio w/ Private Fenced Yard

Welcome to the newly renovated Pop's Garage! If you've stayed with us before, you'll love the upgrades to our kitchen, the bathroom and the new floors throughout. Plus, we now feature a new, memory-foam King bed and sleeper sofa to accommodate parties of 4. The pet-friendly space includes a private and secure fenced-in area, allowing your canine to stretch out and explore. Discover the perfect balance of comfort and convenience at this one-of-a-kind vacation rental

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