Holiday rentals with a kayak in Florida Panhandle

Private Waterfront Retreat: Family & Pet Friendly

Welcome to your own private waterfront, beach, and retreat destination! Recently renovated, this home is the perfect place to unwind, relax, and soak in the beach life! Tucked away on a dead-end street away from the tourist hustle & bustle. - Panoramic views of the sunset - Private 450ft dock with 2-story deck - Paddle boards/yoga mats - 1 acre of serenity - Complete kitchen - Fenced backyard, outdoor dining, fire pit Location: - 16 mins/10 miles to Navarre Beach - 14 mins/8 miles to grocery

East Bay Hideaway — A Private Waterfront Escape

Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

Kokomo Key - 2 minutes to Beach - Private Pool

If you've been searching for Kokomo Key... Here it is—your tropical escape to the islands. White sand, turquoise waters… it’s got all the vibes of a place where time slows down and the only agenda is relaxation. Relax with the whole family at this peaceful beach house with a private pool, hammocks, unobstructed views of Santa Rosa Sound, and a 2-minute walk to the stunning Gulf beaches! We are pet-friendly, but please remember to let us know you are bringing your pets by checking the box!

Blackwater Bay Mae's Cottage

Mae's Cottage is a peaceful little bay house located right off of Interstate 10 in Milton (< 1 mile) and is within steps to the beautiful Blackwater River and Bay. It is approximately 100 yards from water access where you can enjoy fishing, boating, kayaking or just watching the sun set. There is a public boat launch so bring your boat/jet skis/kayaks and fishing gear and head out to the beautiful waters of Blackwater Bay. Relax with the whole family at this peaceful little bungalow.

Hammock Hideaway - waterfront cabin

Backyard oasis on a deep water creek. If you are coming for travel ball, love kayaking and/or just hanging out right on the water, you will appreciate this special hideaway. A fisherman’s/nature lovers dream and truly unique rental experience at this creekside cottage with water frontage on deepwater Hammock Creek. Close to the beach but out of the congestion. We have a multi level backyard with gazebo with swing, fire pit and huge deck. Fully enjoy the wildlife and outdoor activities.

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.

Casa Verde | Heated Pool • Lagoon • Steps to Beach

Between the Beach & the Lagoon - across the street is the ocean & behind the house is the lagoon; it's the best of both worlds. Swim, fish, crab & paddle board in the lagoon, then swim in the ocean & chill on the beach. Rinse off in the outdoor shower & enjoy the heated pool. FYI: pool heating costs extra: $50 per day (for 8 hours of heating - you pick the hours). You're welcome to use the Green Egg grill. We rent kayaks, a paddle board & a jet ski too.

Golf Cart! E-bikes! Heated Pool! Arcade! FirePit

Welcome to "Gone Coastal" Enjoy all that Windmark Beach has to offer with a relaxing stay in this newer home is a 4 bedroom, 2 bath home that is one of the closest homes to the town center and main pool. It is 2 blocks from the beach, a easy 5 min walk or short bike ride to the beautiful white sand of the Gulf coast. This home features all the amenities such as bikes (including two ELECTRIC bikes), 2 paddle boards, and a 6-seater golf cart all included!

Beach & Lagoon Retreat - Private Beach Access

Welcome to Golden Hour! This newly renovated Gulf Shores retreat is just 100 steps from the beach with private, deeded access. Enjoy stunning water views from every bedroom and breathtaking sunsets nightly. 🏡 Sleeps 10 (max 8 adults) | 4 Bedrooms | 3 Ensuite Baths 🍽️ Spacious kitchen | Two living areas | Wrap-around deck 🌊 Beach gear, paddleboards, kayak & more! Located in peaceful West Beach Blvd—your perfect coastal escape

3 Br Waterfront Florida Classic on the Bayou

Enjoy the comfort and beauty of classic old Florida at this beautiful waterfront home. Moments away from white sand beaches and downtown, you are in an oasis of relaxation here at the Florida Classic on the Bayou. This home was thoughtfully designed and cherished by a prominent local family and features rich Florida history and details. It is our pleasure to share this oasis with you.

Wandering Waters Cabin

FISH-HUNT-BIKE-SWIM-KAYAK-GLAMP Come stay on the beautiful Chipola River in the Florida Panhandle. This inviting cabin overlooks the river with a spacious dock that can be used for a variety of water activities. The house is centrally located approximately one hour from Tallahassee, Dothan, and Panama City Beach-the World's Most Beautiful Beaches.

Romantic Seagrove Palmetto Bungalow 30A Lakefront

Welcome to the Palmetto Bungalow! Recently chosen by Brides magazine as one of the top 20 most romantic airbnbs in the country! Truly a special place to unwind, refresh, reconnect, honeymoon or just fall in Love again! This romantic lakefront gem takes you back to yesterday, the simpler times…the way it used to be. Love is in the air.