Holiday rentals with a kayak in Jacksonville

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!

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.

Sunset River Retreat

Escape to this stunning 3-bedroom, family-friendly oasis nestled along Doctors Lake riverfront. With a sparkling pool and breathtaking sunset views every evening, this is the ultimate haven for relaxation and fun. Home has a pool, firepit, outdoor pool table, and direct access to the river, ideal for fishing or kayaking. 30 min to downtown Jacksonville, 10 min from NAS Jax Naval Base. 10 minutes to boat ramp. 2 story house, bedrooms on 2nd floor Inquire for Events ($850 Event Fee, Max 50 ppl).

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.

Oceanfront with Included Golf Cart & Kayak

This fully renovated condo is in The Sandcastles complex within Amelia Island Plantation. It has 1 bedroom, 1 bath, a flex room that can be used as an office or a sleeping space with a king trundle bed. Single kayaks & gas golf cart are included to explore Drummond Park, Walker's Landing, Nature Center, mini golf, multiple shops and restaurants all within Amelia Island Plantation. The location is great, views are incredible and is a very comfortable space for couples, and small families!

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.

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.

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.

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

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.

Lakeside, Water View, Kayak, BBQ Grill, Fire Pit

Save my home, click the <3 in the upper corner! NO cleaning fee! No surprise fees! >Lakeside Wonderland - Lake Asbury >Pet friendly with fee and restrictions >2 miles from Old Ferry Boat Ramp >Backyard + patio with stunning lake views >Minutes from St. Johns River >Sleeps 6 >Kayaks + SUP with waiver >Drip Coffee Maker + Nespresso >Wood burning fire pit >Propane BBQ >Washer + Dryer >Nearby restaurants and shopping >3 days of supplies (TP, trash bags, pods, etc.)

Cowford Cottage

Historic walkable neighborhood, close to the Shops of Avondale for fine dining or the Murray Hill District for nightlife. Enjoy a short walk to Boone Park for its many amenities. Blocks from the Beautiful St Johns River, minutes to Downtown. Home features a spacious kitchen, a covered outdoor patio with bar and TV perfect for grilling, entertaining or watching the game. Sleeps 5. Pet friendly/fenced yard. Dedicated office space with strong Wifi and dual monitors.