Vacation rentals in Callahan

Easy Breezy Bungalow

This charming historical bungalow with views of Trout River and Rolliston Park is situated in a peaceful natural setting, yet is convenient to I-95, Jacksonville International Airport, JAXPORT Cruise Terminal, EverBank Stadium (home of the Jacksonville Jaguars), VyStar Ball Park, Dailey's Place Amphitheater, and the Jacksonville Zoo. The owners live nearby and are available to welcome and assist you. A fifth guest will be comfortable on the sunroom daybed. Please note: This is NOT a party venue.

The Hothouse-Couples Escape: Play-Relax-Reconnect

The HOTHOUSE is a Unique Risquè Stylish Mobile Home (Sleeps 4ppl Max.) Private, surrounded by trees-No neighbors. We welcome couples & friends for anniversaries, honeymoon, or those looking for a reason to escape the world & routines. It is the closest residence to JAX; overnight travelers are welcome. This place is not typical. We seek to fully immerse you in a unique stay & experience. <2mile from the Airport, Shoppes, & Dining. Contact us directly about features & details for THE SWEATSHOP.

Private Getaway

Lovely 2nd floor 2 bedroom apartment over carriage house. Modern stainless appliances in kitchen, 55" LED TV with cable, high speed internet, washer/dryer. Completely furnished and supplied with all household needs. Centrally located between I-95, shopping/restaurants and beach. Check-in is 3:00p-8:00p. No check-in after 8:00p please. When booking please notify me of the estimated time you will arrive. This is a non-smoking apartment. No pets allowed. We cannot accommodate trailers.

Oak Bluff 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.

Holly’s Haven at Puskita Oaks ! Close to Airport

Escape to our charming tiny house getaway, Holly’s Haven @PUSKITA OAKS in Jacksonville is close to the airport. This haven offers a tranquil & country setting with easy access to Jacksonville's populer downtown area and only 15 minutes to Riverside Marketplace & all major highways. Our relaxing retreat is on 4 acres with Grand Oak trees and lots of natures beauty to enjoy. Only 40 minutes to all beautiful beaches. Pets under 40 lbs are welcome but must not be left alone during your stay.

Riverfront Relaxation | Fish, Boat, Unwind

Welcome to Sunrise Suite — a private 2,000 sq ft retreat with breathtaking sunrise views and no shared indoor spaces. Located above the garage, this spacious guest suite features one bedroom, one bathroom, and three comfortable beds within an airy open layout. Large windows fill the space with natural light, creating the perfect place to relax and recharge. Nestled in nature yet minutes from Jacksonville International Airport and major highways for easy access.

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.

Tranquil river cabin with a 1950’s vibe

Watch evening sunsets, have cocktails on the dock or around the fire pit, enjoy boating the St Mary’s River, or bird-watching from the river room of this secluded space. Stargaze from the backyard (no light pollution here!). A boat ramp is nearby for boat launching. (Tie your boat up at our dock during your stay) 45 min. from Jacksonville Fl 45 min. from Fernandina Beach Fl 20 miles to Cumberland Island Ferry 25 miles to Okefenokee Swamp

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. This petite studio is equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.

3 bedroom home with pool

Relax with the whole family at this peaceful place to stay. The neighborhood is small and quiet. The backyard backs up to 4 Creeks Management Area (lots of woods). The backyard is fenced to provide privacy. The pool has night time lighting if you want to enjoy a night swim. If you enjoy bird watching you will love watching the birds out the window in the living room. The hummingbirds love to visit.

Disney Fort Wilderness Cabin – The Outpost

Escape to a rustic North Florida cabin less than 10 minutes from I-95 and just 30 minutes to Fernandina Beach & Amelia Island. Surrounded by peaceful woods and close to state parks, this cozy retreat offers Roku TVs, outdoor seating, and a charcoal grill. Perfect for relaxing, exploring nature, or enjoying dining and shopping nearby — the ideal blend of seclusion and convenience.

Trout River Oasis

Escape to Trout River Oasis, a modern 3-bedroom waterfront retreat on the serene Trout River. Enjoy expansive water views from a large deck, perfect for groups seeking tranquility and convenient lake access. This private home offers a fully equipped kitchen and an open-plan living space, comfortably accommodating your entire group for a memorable getaway.