Family-friendly holiday rentals in Oceanway, Jacksonville

Cozy Riverside Home. Walking Distance To 5-Points!

This home is located in the heart of Riverside. Cozy and aesthetic! You are centrally located in the center of 5-points. Park your car and leave it!! You are within walking distance to everything. We also have fun bikes located on the property. This home is perfect for couples, business travelers, or if you are traveling alone. - Due to Coronavirus, we’re taking extra care to disinfect frequently touched surfaces between all reservations. • Parking is available on the STREET ONLY

The 1910 General Store - residence

This historic country general store, listed on the National Register of Historic Places, is within easy walking distance to art galleries and cultural events, restaurants, bars, night life, and family-friendly activities. This residence is good for couples, solo adventurers, business travelers, families, and furry friends (pets, max. of 2). We are unable to allow guests to host gatherings and house parties. Off street parking available. "Historic hospitality with a southern accent!"

Charming Guest House on Riverfront Estate

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! Enjoy a stroll around the entire estate with owners permission. Owners home is on the property and they are always available. 45 minutes to JAX Beaches. 35 min to St. Augustine.

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.

Waterfront Cottage on Private Island in Preserve

Longvue is an Old Florida house set on private Medicis island in the Intracoastal Waterway surrounded by the Guana/Tolomato Matanzas National Estuarine Research Reserve (73,000 acres) and Stokes Landing Conservation Preserve (300 acres). Private floating dock with tidal access to the IWC. Very private island with 6 residences. The 10 acre island is surrounded by rivers, marsh flats and fresh water ponds. Boat/Kayak to the National Reserve and walk the trails to S. Ponte Vedra Beach.

Cozy, private efficiency: Centrally located

Cute, clean efficiency apartment within a larger home. Completely private with separate entry door. Luxury vinyl "wood" flooring, Memory foam mattress. Appliances include dorm fridge/freezer, toaster oven, microwave, burner, coffee pot. Plenty of storage and a large closet. Only 4 miles from the stadium and downtown. 10 miles from Mayo Clinic and 13 to the beach. Centrally located - a great location for concerts, festivals and other events in the Jacksonville area!

Hidden Gem

This 'beachy' key west style guesthouse is hidden from the street but not the ocean breeze! The beach is only 1 block away and easy to get to by foot. You can't help but to spend your time relaxing on the large front porch. The property is fenced in and has a yard. Guests can use the BBQ, bikes, beach chairs, body boards and cooler, so you don't have to buy or bring your own! The house is between Jacksonville Beach and Atlantic Beach Town Centers.

"Sweet Water" Waterfront Studio Apartment

Experience inter-coastal living in a well-appointed waterfront, upstairs studio guest house. Furnished with a king-size bed, queen-size sleeper sofa & many amenities. Only minutes from the beaches, Mayo Clinic, restaurants, nightlife, Players Championship Golf Course, shopping & more. Conveniently located near lots of activities, but not too close to interfere with your rest & relaxation. Whether on vacation or business, it's the ideal location!

Renovated Beach Escape HTD Pool, Spa, Putt Putt

Newly remodeled – Beautiful 3,000 square foot 5 bedroom beach house. It is only a few minutes drive to the beach (1.2 miles) and close to the Mayo Clinic (5.2 miles). The outdoor area is the absolute highlight of this property. The heated saltwater pool, spa, grilling area, outdoor dining, and sitting area are all fully screened. A new putting green, fire pit, pergola table seating to enjoy your meals outdoors. Game room and PS5 as well.