Family-friendly holiday rentals in Oceanway

Shady Oak Guesthouse

Enjoy your stay at this shady oak guesthouse. It is located on our 2 acres of land with the view of a neighboring lake. Don’t let the size fool you, it has a queen size bed, small kitchenette with fridge, microwave and coffee. The eating area can double as a workspace if needed. It has a full-size bathroom as well. It has a brand new ac and air purifier. It has outdoor seating, privacy fence and keyless entry. Minutes away from JIA, River City Marketplace, the Zoo and the Cruise terminal.

Studio Suite in Beautiful Central Neighborhood

Studio guest suite with queen bed and kitchenette in beautiful Miramar neighborhood, just 5 minutes from historic San Marco. Close to restaurants, grocery, MD Anderson Cancer Center and Wolfson Children's Hospital. Owners live in main house on site but suite has its own private entrance and parking. You will have access to an outdoor dining space and fenced in backyard. Dogs live on premises but will not interfere, although you may hear barking. Sofa bed available if needed, please inquire.

Dream Catcher Cottages at Sweetwater Creek

Come stay in our North Florida Paradise~Secluded & Quiet yet minutes from Shopping, Restaurants, the Zoo, 15 minutes from the airport or downtown Jacksonville, Beaches, State Parks. Enjoy the huge covered screened deck overlooking the pool, pond and enjoy expansive views of the creek and conservation protected marshes. Nicely outfitted kitchen with tons of countertop space or BBQ your favourites on the Weber grill on the open deck right outside the kitchen door. Lots of room~wifi & internet.

Sugarberry Tiny Home on 2.5 Acres with Pond/Patio

Relax at this quaint and laid-back getaway located close to restaurants, airport, cruise terminal and major highways. The property is near nature preserves and state parks that are ideal for hiking , fishing and boating or just relax in any of our many beautiful beaches and enjoy all the fine dining. For entertainment and event venues , Riverside/Downtown is under 30 minutes away. A great place to relax and rest after a day of activities or on your way to your final travel destination.

Back In Time

This is a unique 200 ft small tiny house with a covered porch with 2 rocking chairs for enjoying the outdoors. It is decorated with family antiques even a 4 ft claw foot tub turned into a shower.... If you want the feel of a nice relaxing country atmosphere with woods and nature this is the place for you. We live on a dead end rd which is quite and very safe. Our 2 story house is next to the tiny house but you have your own space and yard. Your privacy is respected at all time.

The Little House on Jupiter

Good vibes only at La Casita. Stylish, peaceful & private. When it comes to choosing your home away from home- the details matter. Kitchen is equipped with fridge, microwave, air fryer and hot plate. Coffee, hand soap, dish detergent, shampoo and conditioner provided. The bed is full sized. Enclosed side yard. Excellent central location. 10 minutes to the highway, St. John’s Town Center & UNF. 20 minutes to the beaches, downtown & Mayo. No smoking is permitted inside.

Cute Pool Cottage in the Historic District

Poolside guesthouse in a lush tropical garden yard-this studio with 1 bedroom/1 bath is in Jacksonville’s Avondale Historic District, and just steps away from the popular Shoppes of Avondale with its restaurants and quaint shops. Its perfect for business travelers, singles, or couples. The space features a super cozy queen size bed with luxury linens. There is also a mini-kitchen with microwave, toaster oven and compact refrigerator. There is no stove.

Cozy Cottage in Springfield, Downtown Jax

🤍 We can't wait to host you! The Cottage on 4th is located in the eclectic Historic Springfield neighborhood in Jacksonville's urban core. Situated in close proximity to awesome restaurants, coffee shops, breweries, and entertainment venues. Located 1.5 miles or less from TIAA Bank Field, Daily’s Place, Vystar Veterans Memorial Arena, and 121 Financial Ballpark (Jacksonville Jumbo Shrimp stadium). 13 miles from JAX airport and 16 miles from the beach.

The Cozy Hideaway- Airport, Cruise, Zoo

Kick back and relax in this calm, stylish space. We offer a comfortable place for 4, with a queen bed and a sofa that pulls out into another queen. We offer parking for cruise getaways, and are 8 minutes away from port! Feel calm and relaxed in presence of the beach. Only 25 minutes from the Beach. Right off 95. This is a tiny house located on our property. Has complete own entrance and building. Total privacy with gate around entire property.

Enchanted Forest: a Magical Luxury Studio

Lost to time, at the end of a long forgotten forest path, where dappled sunlight outline trees, moss, and stone. Enjoy the luxurious richness of satin, velvet, chandeliers and candles. Looking to escape, we’d love to share the path to this hidden destination in Historical Riverside. Equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.

Tiny House - Urban Sanctuary

Indulge in serenity at this cozy tiny home, nestled in a backyard community away from the city's hustle. Unwind while sipping your morning brew on the porch to the symphony of birdsong. With a functional kitchenette and full bathroom, it's the perfect home away from home. Book now and experience a harmonious blend of urban charm and tranquility.

Hip + Modern Florida Hideaway

Located in historic Murray Hill, our Florida hideaway is a fully renovated hip and stylish private guesthouse brimming with natural light and great vibes! Each room is keenly decorated with high-end modern furniture along with curated vintage art and decor. This space is packed with character and provides all the comforts of home.