Holiday rentals with breakfast in Intracoastal Waterway

A spacious living area is presented with a light-colored sofa and a matching ottoman, complemented by a deep blue armchair. The room features a decorative round mirror, hardwood flooring, and an archway leading to a dining space with a table for six, illuminated by natural light.

4.98 out of 5 average rating, 286 reviews

Luxurious Craftsman in Historic San Marco

Never Drive Again! Immaculately renovated San Marco Bungalow, just a minute from excellent restaurants, retail, entertainment, hospitals & easy transit (via San Marco's FREE Beachside Buggy App) to everything else. Features include an inviting front porch, interior foyer, charming living room w/gas fireplace, new kitchen w/SS and granite, indoor laundry, historic architectural features, and private backyard w/ sitting area, fire pit, games & BBQ! Incredible location with unmatched walkability!

5 out of 5 average rating, 24 reviews

An outdoor area is depicted, featuring a salt-water pool surrounded by lounge chairs and shaded by a red umbrella. Permanent string lights provide soft illumination. Tropical landscaping and a covered space in the background suggest an inviting environment for relaxation and leisure.

Home in St. Augustine

Luxury Home with Pool, Pickle Ball and Hot Tub

Your family will be a walk away to downtown Saint Augustine when you stay at this centrally-located place. Everything you need is at the Pelican’s Oasis from the outstanding outdoor area with a salt water pool and covered living area to an elegant indoor entertainment area with bar, ice machine and beer fridge. Covered Pickle Ball court, Hot Tub and 6 seater Golf Cart ( for additional fee). Plenty of room throughout the house to enjoy different seating areas and even a selfie stage with props.

A bungalow with a welcoming facade is surrounded by mature trees and greenery. The front yard features well-maintained plants and a pathway made of stones. A covered porch adds character to the home, providing a cozy entrance along the tree-lined street.

4.88 out of 5 average rating, 100 reviews

Colorful Bungalow Sleeps 6 - Pet Friendly!

This colorful, family friendly, pet friendly, bungalow provides beds to comfortably sleep 6 guests and is located on a quiet tree-lined street in the Historic Murray Hill section of Jacksonville. It features a full kitchen, and fenced backyard with charcoal grill. Enjoy the convenience of an eclectic mix of local restaurants, shops, bars and parks, within just a 10 min walk or a quick car ride. Easy interstate access to I-95 and I-10 and convenient to downtown Jacksonville and the Beaches.

A charming single-story house features a light exterior with a blue front door. Two symmetrical windows provide ample natural light, framed by well-kept greenery. A stone step leads up to the entrance, with a neatly manicured lawn extending to either side.

4.99 out of 5 average rating, 303 reviews

Riverside Retreat with Bikes & Fire Pit

This charming bungalow is located in the heart of walkable Riverside; Jacksonville's most fun neighborhood. Enjoy a king bed, smart speakers, fast WiFi, and streaming channels, as well a fully stocked kitchen and a backyard with adirondack chairs, an electric grill, a fire pit, and even 'smores kits. Use our custom recommendation guide to explore local shops and restaurants on our cruiser bikes (complete with cup holders and cell phone holders). Private driveway parking is included, too.

Bungalow in St. Augustine

A charming bungalow is framed by lush palm trees, with a welcoming teal front door at its center. A stone pathway leads through gravel landscaping adorned with greenery, creating an inviting approach to the home.

4.98 out of 5 average rating, 279 reviews

"Flagler Shack"- a funky tropical oasis!

"Flagler Shack"- funky, cozy, cool...renovated island bungalow! * 10 min walk to downtown(over Bridge of Lions) * 10 min bike ride to the AMP(farmers market, concerts) * Awesome bars and restaurants literally out your back door...Odd Birds, Blackfly, Sarbez, Llama, Slugs Pub, Gas Fresh Island Market, Osteen’s, Osprey Tacos, Mojos Tacos * 15 Min walk to Conch House Marina and Restaurant * 20 min bike ride to beach at Anastasia State Park * 5 min drive to Saint Augustine Beach

Guest suite in St. Augustine

A tranquil bedroom showcases a queen bed adorned with a leaf-patterned duvet cover. Two bedside lamps cast soft light on either side, while bright blue and green walls create a soothing ambiance. Light filters through shuttered windows, enhancing the warm wooden floor.

4.83 out of 5 average rating, 245 reviews

Historic St. Augustine Gateway

Experience the allure of St. Augustine from our charming private suite. Nestled within a leisurely stroll of the historic heart of St. Augustine and a mere 5-minute drive from its world-renowned beaches. Your sanctuary consists of two distinct areas – a gracefully adorned bedroom featuring a comfortable queen bed, and a cozy den with sofa. Connected to our residence with a separate private entrance and a quaint deck, this suite affords you the utmost privacy and independence.

Apartment in Jacksonville

The studio features a spacious bed with a light-colored blanket and decorative pillows. A cozy sofa sits in the corner, accompanied by a coffee table. Green plants are placed throughout, and ample natural light enters through a window, complemented by thoughtful décor on the walls.

5 out of 5 average rating, 154 reviews

The Cozy Basement in San Marco

Make yourself at home in this studio-style apartment located in a quiet neighborhood with a kitchenette and full bathroom that features modern updates. Centrally located, less than 5 minutes from historic downtown San Marco with trendy restaurants and shopping, just minutes away from all the shops and nightlife in the village square. Less than 15 minutes to Riverside and downtown Jacksonville including multiple hospitals. Also only 30 minutes from the airport and beaches.

5 out of 5 average rating, 73 reviews

An outdoor area features a grassy lawn with a corn hole game and an inviting stone fire pit. Adirondack chairs surround the fire pit, and a gazebo with string lights can be seen in the background, enhancing the space's relaxing atmosphere.

Home in St. Augustine

4 Min Walk To Beach! Hot Tub•Golf Sim•Fenced Yard

Wake up hearing waves, stroll to the beach with coffee, and come home to your own golf simulator, hot tub, and lanai oasis! This is St. Augustine paradise on Vilano Beach. 🩴4 Min Walk To The Beach 👣Walk to Publix, Restaurants & Pier ⛳️ Golf Simulator 🚿Hot Tub 🛁 Rainfall Shower 🔥Propane Grill & Fire Pit 🌴Screened in Lanai 👶Baby/Toddler Friendly 🐶 Dogs Welcome ($140/dog) 🏖️ Beach Gear & Games 🛜1G Wifi Planning Ahead? ❤️ this listing in the top right corner

4.97 out of 5 average rating, 102 reviews

The bedroom features a king-size bed with a quilted bedspread and decorative pillows. A bedside lamp sits on a dark wooden nightstand. Large windows with drapes allow natural light into the space, creating a serene environment. A comfortable chair is positioned near the window.

Condo in St. Augustine

Luxury Golf & Spa condo in Beautiful St. Augustine

Beautiful 1 bedroom pristine condo unit has it all. Comfortable king size bed, privacy, full bathroom with roman bathtub, washer/dryer, full kitchen with all the utensils you will need, two flat screen tv's, fast free wifi, private balcony overlooking lush gardens with a fountain. The Laterra resort boasts a plethora of amenities right outside your doorstep. Heated pool, pool with waterfall feature, hot tub, tennis courts, award winning Golf and restaurants nearby!

Home in Jacksonville Beach

The exterior of a two-story beach house is showcased, featuring a light-colored facade and a silver metal roof. A spacious driveway leads to a two-car garage. Lush green landscaping surrounds the home, with palm trees adding to the tropical feel.

4.93 out of 5 average rating, 273 reviews

2 Kings + 2 bunks, Walk to Beach - $0 Host fee

This 2-story 3 BR/2.5bath, 1700 sq ft. elegantly furnished vacation beach house is within 3 blocks to the beach, restaurants, grocery, and shopping. Experience melting into TWO TempurPedic king beds, enjoy a refreshing multijet spa shower, sip coffee or drinks on the large master balcony, or zen garden patio, or watch various prepaid streaming apps on multiple large 4k TVs throughout the house.

Apartment in St. Augustine

A cozy dining area is depicted with a round black table and two wooden chairs. A bottle of water rests on the table, while light enters through a glass door leading outside. The entrance to a bedroom is visible in the background.

4.96 out of 5 average rating, 196 reviews

Charming Sanchez 2 ~ 5min drive to downtown/Bikes

This quaint downstairs unit located just steps to uptown shopping/restaurants and a short drive to the main drag of historic downtown. Catch a trolley that will take you to 24 stops throughout downtown or enjoy a 15-20min stroll to downtown St George St. where shopping and restaurants are plenty! You are also a short walk to the Fountain of Youth and the Old Jail! No car needed!