
House holiday rentals in Fleming Island
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Top-rated house rentals in Fleming Island
Guests agree: these houses are highly rated for location, cleanliness and more.

1920 Carriage House on Riverfront Estate- Weddings
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

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

Tree Tops: Where Everything is brand new
Take it easy at this unique and tranquil getaway nestled in the Tree Tops. All new appliances, furniture, electronics, sheets, and towels are found in this totally remodeled home. No expense was spared in making your stay as comfortable as possible. This is your perfect get away from the hustle and bustle of life. Enjoy your first cup of coffee on one of 3 porches. Tree Tops is also close to popular attractions, located 6 miles to Vilano Beach and 4 miles to St. Augustine’s historic district.

Historic Designer Home • Luxury Baths • Steps2DWTN
Off Street Parking for 2 vehicles 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.

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.

Nature Cozy Home
Located in Orange Park FL , this rural, rustic, colorful getaway can be your home away from home! Guests can enjoy the forested and vintage scenery that reminds one of simpler times. The designated parking area is indicated by the, sign of three flowers at the left side of the driveway. Guests will also have their own seating area. Please note we have another Listings: Retreat Mobile Camper (back to house) and Guest Suite (attached to house)on the property! , with everything private Thanks

Modern E. Orange Park Home 6 bed Fence Beach 45 Mn
New Stylishly renovated home just West of Fleming Island in Middleburg, South of Orange Park, West of Jacksonville Florida. Christmas 365! Farmhouse style, TV’s in all bedrooms, with a touch of Christmas theme. 6 beds, Fenced yard, 75" LED TV, front/back porches available up to 10 people. Beaches approx. 40 minutes The home is close to restaurants, grocery stores, banks, gas stations, main hospital(2+miles). There are lakes and rivers locally to fish/boat, parks, shopping, and trails:).

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.

King bed, Lake View, sleeps 8, 6 TVs, Public Pool
Escape to our cozy retreat! You'll unwind in style with up to 6 beds in our safe neighborhood, close to Publix and restaurants. You'll explore nearby beaches, parks and attractions or day trip to St. Augustine and Orlando. You'll enjoy serene lake views and backyard fishing. You'll love our top-notch amenities, including a recreational pool with slide, lap pool, basketball, fitness center and playground. You'll create unforgettable memories - book now! We look forward to hosting you.

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.

St Augustine Entire Home, King Bed, Pet Friendly
Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

Sunset near the Lake/12guests/4bdrs/2baths
Welcome to our beautifully remodeled vacation home on a safe, quiet street. Enjoy a stylish full kitchen, cozy living and dining areas, and direct lake access for fishing. Conveniently located near downtown Jacksonville, with easy access to Walmart, restaurants, beaches, Blue Springs, historic sites, NAS Jax, the airport, seaport, and local colleges. We look forward to hosting you and making your stay comfortable and memorable!
Popular amenities for house rentals in Fleming Island
House rentals with a pool

Historic Hollywood House w/Pool

Your Home Away From Home

Cozy Home with Heated Private Pool and Patio

Luxury Pool Retreat • Taste of Britain

San Marco Home • Pool, Hot Tub, Grill

Pool Home with Game Room in Heart of Jax Beach!

Oasis in the Hill

Retreat on the river
Weekly house rentals

Peaceful Getaway in the Heart of Jacksonville

Ideal Location: Walk to wedding venue & eateries!

Cozy 4BR Near St Johns River

OP Retreat | 3BR | 2BA | Pool | Fenced | Quiet

*Gorgeous Home! Safe, very peaceful*

Zen Flamingo: Poolside Peace Near Beaches and TPC

Beautiful Lake Mandarin Home

KAYAKERS RETREAT~King Bed Sleeps 8~Waterfront
Private house rentals

Premium House fireplace, Mini Golf and Large Patio

Easy Breezy Bungalow

Eagles Nest on Lake Ponte Vedra

Fifties Fun

Hidden Gem: Nocatee Farm Oasis

Cottontail Manor Ortega 4BR across from River

Orange Park Oasis 2bed/2bath

Villa Marita B&B
When is the best time to visit Fleming Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £108 | £125 | £145 | £102 | £103 | £101 | £108 | £111 | £96 | £98 | £100 | £103 |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°C |
Quick stats about house rentals in Fleming Island

Total holiday rentals
Explore 20 holiday rentals in Fleming Island

Nightly prices starting at
Fleming Island holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 1,110 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Fleming Island holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Fleming Island rentals

4.9 Average rating
Fleming Island stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Crescent Beach
- University of Florida
- EverBank Stadium
- St Augustine Amphitheatre
- VyStar Veterans Memorial Arena
- Saint Augustine Town Plan Historic District
- Paynes Prairie Preserve State Park
- Kathryn Abbey Hanna Park
- Lightner Museum
- St Johns Town Center
- Fountain of Youth Archaeological Park
- Summer Haven st. Augustine FL
- TPC Sawgrass
- Depot Park
- Vilano Beach Fishing Pier
- Adventure Landing Jacksonville Beach
- University of North Florida
- Fort Clinch State Park
- Ravine Gardens State Park
- Memorial Park
- Little Talbot
- St. Augustine Alligator Farm Zoological Park
- Marineland Dolphin Adventure
- Catty Shack Ranch Wildlife Sanctuary





