Holiday rentals in Penney Farms

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

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.

Guest House-Enchanted Oaks Estate-Weddings-Dock

Pretty Guest House situated on majestic 5 acre riverfront estate on the St. John’s River with park-like grounds filled with colorful azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to incredible hawks and bald eagles overhead! Wake up to a magical sunrise each day! Bass Pro Shop did a photo shoot here for their Spring 2025 catalogue! Owners home is on the property and they are always available. 45 minutes to JAX Beaches. 35 min to 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.

Modern Green Cove Springs 6 Bed Fence Beach 45 min

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:)

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.

Haystays Farm-Cozy, Charming, Country, Modern Home

Welcome to our special farm house! The home sits on 1.5 acres that is perfectly located on the Orange Park and Fleming Island line. Our location is ideal to everyone! We have plenty of space that makes our farmhouse so AMAZING! You will experience the feel of country living with all the perks of great restaurants, shopping and convenience of being near everything Jacksonville has to offer. Our home is super clean with many amenities to make you feel at home. We love it here and so will you!

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.

Luxury Home w/ Glass Room & Patios

Spectacular Inside and Out This magnificent 2940 sq foot home is in a prestigious lakeside neighborhood. It offers a large open concept living area with an adjoining 400 sq foot climate controlled sun room with a pocketing glass interior wall; to bring the outside in and the inside out. The exterior of the sun room is constructed of glass doors which can also be opened and stacked to facilitate an open air porch. Owner lives in the neighborhood and is quick to respond to your needs.

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.

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.

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.