Holiday rentals in Penney Farms

The two-story white house features a welcoming entrance with a central door flanked by large windows. Adjacent to the entrance, two armchairs are positioned around a small table on a circular patio, surrounded by lush green grass and decorative potted plants.

4.99 out of 5 average rating, 127 reviews

Enchanted Oaks Estate-Weddings -Carriage House

1920 Carriage House on lush private estate. Renovated and charming! Situated on secluded, majestic 6 acre riverfront property on the St. John’s River. Enjoy park like grounds filled with azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Bass Pro Shop shot their Spring Catalogue here! Owners home is on the property and they are always available

4.96 out of 5 average rating, 206 reviews

The back patio features a cozy seating arrangement with a modern sofa and a small table. Twinkling string lights illuminate the area as evening approaches, providing a warm ambiance. A dining table for four is visible on the patterned outdoor rug, amidst a spacious fenced yard with trees.

Home in Fleming Island

The Flemingo- Game Room 3 Kings

Welcome to the Flemingo where can relax on the back patio with a glass of wine and twinkling string lights above. You'll watch the dogs and kids play in the large fenced yard while throwing a frisbee (provided). You'll love cooking a delicious meal in the spacious kitchen. You’ll have a blast in the garage game room! Battle it out on the air hockey table, foosball, darts or boxing bag. At night, the kids will hang out in the garage game room, in the living room playing board games or on

Superhost

A modern single-story home is showcased, featuring a well-manicured lawn. The front facade includes a double garage, a covered entryway, and several palm trees lining the pathway. Clear blue skies provide a bright backdrop to this inviting exterior.

4.9 out of 5 average rating, 20 reviews

Spacious Family-Friendly

This family-friendly and amenity rich neighborhood promotes an active, healthy lifestyle for residents of all ages. The sand volleyball courts, competition swimming pool, fitness center, tennis complex and walking trails are luxurious additions for any exercise buff or sports lover. Kids can enjoy going down the water slide at the beach-entry water park, throw a birthday celebration in the party room in the Residents' Club, or have a relaxing picnic with the family at the neighborhood pavilion.

4.94 out of 5 average rating, 71 reviews

A serene outdoor space features a private saltwater pool, enclosed by a mesh screen. Two pink flamingo floaties rest on the water. Comfortable lounge chairs provide seating alongside lush greenery, enhancing the inviting atmosphere of the retreat.

Home in St. Johns County

Zen Flamingo: Poolside Peace Near Beaches and TPC

Welcome to the Zen Flamingo—a peaceful, stylish retreat in St. John’s, FL! Nestled between St. Augustine and Jacksonville Beach, our home offers a relaxing getaway with a private pool, modern comforts, and smart home features. Whether you're lounging by the saltwater pool, exploring local shops, or streaming your favorite shows, you’ll find everything you need to unwind. Enjoy nearby dining, shopping, and beaches.. View the full Zen Flamingo experience using the QR code in the photo gallery.

5.0 out of 5 average rating, 156 reviews

Home in St. Augustine

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

A modern living area features a spacious gray sofa and a festive Christmas tree adorned with decorations. Stockings hang from the fireplace, while a large TV is mounted on the wall. Natural light floods the space through nearby windows, enhancing the welcoming atmosphere.

4.96 out of 5 average rating, 136 reviews

Modern Green Cove Springs 6 Bed Fence Beach 45min

New Stylishly renovated home in Green Cove Springs just South of Fleming Island, Orange Park, Middleburg, West of Jacksonville Florida. Christmas 365! Farmhouse style with a touch of Christmas theme. 7 beds, Fenced yard, 65" LED TV, fast internet, front/back porches available up to 10 people. Beaches approx. 45 minutes. Camp Blanding 25min Close to restaurants, grocery stores, banks, gas stations, main hospital 8+miles). There are lakes and rivers locally to fish/boat, parks, and shopping:)

Superhost

An open-concept living area features light wood flooring and neutral-colored walls. A spacious sectional sofa faces a large television. The kitchen showcases wooden cabinets and modern appliances, with a breakfast bar that includes several stools. Natural light enters through multiple windows.

4.86 out of 5 average rating, 148 reviews

Cozy 3 bedroom house in town, bikes included!

Welcome to the Sunny Side Up Villa in charming Green Cove Springs! This private home is centrally located in historic downtown and includes bicycles for you to tour the city and visit all the sights. Spring Park and the St. John's River are just a mile down the road. The three bedroom home sleeps eight and features a brand new king bed in the master suite. The open concept living room and kitchen are great for entertaining and the backyard is completely fenced in for your four-legged pals.

A welcoming two-story home is set among lush greenery, showcasing palm trees and manicured landscaping. A clear pathway leads to the entrance, framed by vibrant flowering plants. The exterior features a blend of muted blue and gray siding under a dark roof, enhancing the serene surroundings.

4.97 out of 5 average rating, 33 reviews

Charming Retreat w/ Bikes

Welcome to your serene stay in the heart of Green Cove Springs — where river views, small-town charm, and local attractions create the perfect Florida getaway. Located just one block from the beautiful St. Johns River and within walking distance of downtown, the downtown marine, and the iconic Clay Theatre — a favorite wedding venue. Whether you're in town for a wedding, work, outdoor adventure, or just a quiet riverside escape, you'll love the unbeatable location and charming local vibe.

4.99 out of 5 average rating, 173 reviews

An outdoor space features a stone patio with a circular arrangement of four black chairs surrounding a fire pit on gravel. Verdant landscaping and trees provide a natural backdrop, enhancing the tranquility of the area.

Home in Fleming Island

Rustic Owl in Fleming Island with 2 Kings

From our family to yours. Located in the heart of Fleming Island, Rustic Owl was designed and appointed with extended family in mind. We wanted a space for families to visit, relax and enjoy each other.... while being comfortable. This gem offers comfy beds, smart TVs, an open floor plan, laundry facilities, upgrades throughout and with inviting outdoor spaces that overlook a rustic nature preserve. Super clean, Super Fast Wifi and well appointed amenities. Level 2 EV Charger.

Superhost

Bungalow in Green Cove Springs

Dragonfly Bungalow on 1.5 acres close to downtown

Updated 1930s Bungalow on 1.5 acres . Duplex type home as a separate apartment with it's own entrance is in the back of home. Close to downtown Green Cove/Fairgrounds/access roads to Jacksonville & St. Augustine. Updated kitchen with everything you need to prepare meals. Separate dining area/living room with large smart tv. Fast wifi. 2 bathrooms with updated fixtures. Enjoy a cool breeze on the covered front porch, which has beautiful wicker furniture and a wicker porch swing.

4.8 out of 5 average rating, 88 reviews

5.0 out of 5 average rating, 6 reviews

Home in St. Augustine

Hidden Sanctuary | Heated Saltwater Pool | FirePit

Welcome to The Hidden Sanctuary A heated and cooled saltwater pool, nearly an acre beneath moss-draped live oaks, and privacy from the surrounding homes. The Hidden Sanctuary is Old Florida privacy with mid-century bones, 25 minutes from historic St. Augustine and a few blocks from the St. Johns River. Coffee on the screened porch. Afternoons in a pool that's swimmable in August. Nightcaps by the fire pit. An outdoor rainfall shower tucked into bamboo cut from the property.