Holiday rentals with a kayak in Intracoastal Waterway

Home in Green Cove Springs

Two wooden chairs are placed beside a calm body of water, creating a serene setting. A small table holds a bottle of red wine and two glasses, accompanied by a plate of grapes. A light blanket drapes over one chair, enhancing the cozy atmosphere.

4.9 out of 5 average rating, 48 reviews

KAYAKERS RETREAT~King Bed Sleeps 8~Waterfront

*Water Front* Free Kayaking * Master bed w/private balcony & water views* Come relax with friends, family or have a romantic getaway at this, newly renovated, water front retreat. Enjoy fishing, kayaking, manatee and the most amazing sunsets. Have a glass of wine on the dock, s'mores by the fire pit or throw some steaks on the grill and enjoy the huge back deck The property is beautifully situated on Governors Creek and famous for flat water kayaking. Bring your friends, your family and enjoy!

A vibrant sunset casts a golden hue across the calm water, with silhouettes of docks and a distant boat in view. The sky is filled with layered clouds, creating a serene atmosphere that invites relaxation and reflection.

4.91 out of 5 average rating, 307 reviews

Serenity and Amazing Views - Home on River w/ Pool

Beautiful House: Quiet with all amenities on deep water with pool. 12 minutes from Jax Airport, 5 min from Zoo and 10 min from Cruise Ports. Jax Beaches are just a short beautiful drive. Downtown, Stadium, Arena etc. 10 min Lounge on the deck or sit pool side while watching the sunrise/ sunset. Bring your kayaks and paddle across the river to the zoo, or find sharks teeth on the river islands. Fish off the dock and catch some of Florida's best: Reds, Trout, Flounder, Snapper, Blue Crabs.

Camper van/Motorhome in Jacksonville

A large swimming pool is bordered by a stone patio, featuring several loungers and umbrellas. Lush palm trees surround the area, providing a tropical feel. In the background, the river can be seen beneath a partly cloudy sky.

4.96 out of 5 average rating, 256 reviews

Couples clothing optional escape hot tub deck

You'll love this unique and romantic escape. Designed to create an intimate setting to enhance your time together. The RV is quite large and fully equipped . Master bedroom features a cashmere topped California king bed. The property has so many amenities starting with a very large pool, lighted at night. A dock on the river to enjoy the views. Access to kayaks on premises. There’s a private clothing optional area/deck with a massage table , hot tub and loungers. We recently added a fire pit.

A spacious living area features a stone fireplace beneath a mounted TV. Comfortable seating is provided by a light-colored sofa and a green loveseat. Natural light streams in from two windows, enhancing the neutral-colored walls and wooden flooring. A ceiling fan offers a cooling element to the space.

4.93 out of 5 average rating, 15 reviews

New! Lakefront Home—Near Mayo & JAX Hotspots!

Welcome to this peaceful lake-house retreat with a first-floor main suite for ultimate convenience! Located in a quiet neighborhood, yet just minutes from Jacksonville’s beaches, Mayo Clinic, St. Johns Town Center, and major attractions like TIAA Bank Field, JAX Airport, JAXEX, the Zoo and +10 Museums! Enjoy waterfront views, a grill-ready backyard, a private workout zone, smart TVs in every room, fast Wi-Fi, seamless self check-in, and a dedicated workspace—perfect for business or leisure.

4.96 out of 5 average rating, 136 reviews

The exterior of the mid-century bungalow is surrounded by lush landscaping and palm trees. An expansive deck is visible, offering a space for outdoor relaxation. The green yard features a variety of shrubs and plants, contributing to a serene, natural atmosphere.

Flat in St. Augustine

*1 Block From the Beach! 5 min Drive to Downtown *

In a quiet Vilano Beach community this mid-century bungalow with expansive deck is a beach lovers paradise. Just a stones throw away from one of the most beautiful and private beaches Florida has to offer, and a short drive or water taxi to historic downtown St Augustine, this is truly a gem of a location. You can walk to Publix, bars, restaurants, coffee shops, pier, water taxi, and more. This guest apartment of a 2 story duplex is on the second floor, which has a private entry and parking.

Townhouse in Jacksonville Beach

4.87 out of 5 average rating, 39 reviews

4BR Beach Escape • Steps from the Sand

Welcome to your ideal beach getaway! This updated two-story home is perfect for families or groups. Just four blocks from the beach, it’s easy to enjoy sun, sand, and surf any time of day. Back at the house, the open-concept kitchen and living area offer plenty of seating for meals, or just relaxing together. Step outside and enjoy your favorite channels through outdoor Bluetooth speakers, or spend the afternoon playing on the mini golf course or at the garden after a fun day by the ocean.

4.99 out of 5 average rating, 139 reviews

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

Home in St. Augustine

2023 Lux Home 4bd/3.5ba + SaltPool + HotTub + Walk2Beach

* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - gorgeous quiet beach * 5.5 miles- historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

Guest suite in Jacksonville

A spacious bedroom features a large bed with a neutral-colored spread and an array of patterned throw pillows. Light filters in through two large windows, with a view of greenery outside. A simple nightstand stands beside the bed, enhancing the room's tranquil aesthetic.

4.89 out of 5 average rating, 57 reviews

The Waddle Inn

Peaceful modern farmhouse 2-bed, 1-bath private 2nd-floor suite on our 2-acre creekfront mini farm. Built in 2023, it offers high-quality linens, smart TV, and reliable Wi-Fi. Meet our rescue draft horses, friendly chickens and curious turkey; guests are welcome to help feed treats. Enjoy pool, firepit and on-site kayak rentals on the creek to the St. Johns River. 30–35 minutes to beaches, NAS JAX, TPC Sawgrass and historic St. Augustine. Perfect for couples, families and remote work.

A serene beach scene captures a palm tree alongside the water, with gentle waves reflecting a colorful sunset sky. The shoreline is lined with pebbles and grasses, while silhouettes of distant structures are visible on the horizon.

4.94 out of 5 average rating, 88 reviews

Marshside Getaway Near Hanna Park Relax & Unwind

Discover tranquility at this beachside home, boasting stunning marsh views and a waterfront patio/dock. Just a stone's throw from Hanna Park's surfing, scenic trails, and disc golf. Experience peaceful living near Atlantic Beach's diverse dining and shopping, blending seclusion with convenience. Within 3 minutes of Hanna Park and 5 to Atlantic Beach's lively atmosphere, this charming cottage is an ideal Jacksonville escape for those seeking a blend of serenity and surfside adventures

5 out of 5 average rating, 17 reviews

A wooden balcony offers a serene view of the water and surrounding wetlands. Two wicker chairs are positioned beside a small table, with a guitar resting against one chair. A notebook is placed on the table, inviting quiet reflection.

Home in St. Johns County

Eagles Nest on Lake Ponte Vedra

Eagles Nest on Lake Ponte Vedra is a unique hidden gem nestled among coastal oaks across the street from the Atlantic Ocean. You’ll have access to a true nature get away rarely seen by even most residence of NE Florida. Redfish and Trout are abundant - kayaks are available for a leisurely paddle or a fishing adventure. Sleeping arrangements - king in bedroom, double in living room, 2 fold down chairs in loft. A $400 security deposit is required to be returned if nothing damaged.

The charming craftsman-style exterior features a welcoming porch with light fixtures and a red front door. Lush greenery and flowering plants enhance the front yard's natural beauty, while a paved pathway leads up to the entrance, contributing to the inviting atmosphere of the home.

5 out of 5 average rating, 26 reviews

Willowbranch Bungalow

Charming 1920s craftsman directly across from Willowbranch Park in the heart of Riverside/Avondale. Two queen bedrooms plus office w/available air mattress. Cozy living room w/brick fireplace, built-ins, and Samsung Frame TV. Large well-equipped kitchen. Dining room w/original artwork, and vintage record collection. Beautiful Southern front porch and backyard complete w/ Solo Stove, grill, string lights, and raised gardens. Steps to King Street, Five Points, and Avondale.

A modern kitchen is equipped with stainless steel appliances and a spacious countertop. A bowl of fresh vegetables sits near a double sink. A laundry area can be seen through a window next to the kitchen, with natural light illuminating the space.