Holiday rentals with a kayak in Santa Rosa Island

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Top-rated rentals with kayak in Santa Rosa Island

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Top guest favourite

Flat in Gulf Breeze

4.95 out of 5 average rating, 214 reviews

Redfish Loft, private waterfront Apt. on East Bay

Light airy open floor plan " pet friendly with fee " loft style apartment with private bedroom. Watch the blue herons & dolphins, sit on one of two private decks sipping coffee as you watch the sunrise on the Bay. Paddle the clear waters in our kayaks or bring your SUP. Cook your fresh catch on your private grill or visit a local seafood restaurant. Private, secluded, neighborhood. Join us @ Fire pit ..is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

Guest favourite

Campervan/Motorhome in Navarre

4.86 out of 5 average rating, 170 reviews

Bayfront Forest Camper with kayaks/nature trail

The best of both worlds. Our 11-acre waterfront family’s retreat is the ideal getaway for outdoor enthusiasts and beach lovers. With RVs on the front of the property and the occasional tent camper dispersed through out the acreage, you’ll enjoy time away from the crowds walking the mulched trail to the water or using the two kayaks provided for guest use. We offer additional experiences. Outdoor brunch for two/group, afternoon teatime, boho picnic, s’mores bundles, etc. Message with interest.

Guest favourite

Cabin in Mary Esther

4.91 out of 5 average rating, 208 reviews

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!

Well furnished private one bedroom cottage with sunroom, patio, and carport. Full kitchen with bar counter. Has washer/dryer! There's a fenced yard with small deck, perfect for dog owners. The home is situated under shady oak trees with access to waterfront on Santa Rosa Sound. You can enjoy playing with the pooch, swimming, boating, kayaking, fishing, and viewing beautiful sunsets. It's a perfect location for visits to Hurlburt AFB, or vacationers seeking easy access to Ft. Walton and Navarre.

Guest favourite

Townhouse in Navarre

4.91 out of 5 average rating, 103 reviews

Pet Friendly/ Waterfront/ Private Fishing Pier!

Waterfront dream home with incredibly views of Santa Rosa sound. You'll walk in to a fully renovated, private beach house featuring open floor plan where you can spend time with the whole family, enjoying the panorama. Catch the sunrise from the top balcony outside of the master bedroom. Watch for dolphins from your lounge chair on your private beach during the day. Take the kayaks out for paddle in the waves. Enjoy a sunset walk on the private dock. Star gaze from the huge deck in the evening.

Top guest favourite

Apartment in Pensacola

4.95 out of 5 average rating, 329 reviews

Cozy Bayou Cottage - just steps from the water

Are you looking for a comfortable, clean place to relax in an established and desirable area of town while visiting beautiful Pensacola? Then look no further! The Cozy Bayou Cottage is located just steps from the water along Bayou Texar and only minutes from the downtown entertainment district and our pristine beaches. Enjoy a morning walk along the waters edge under the oak trees, check out the neighborhood beach or let this location serve as your hub while enjoying all Pensacola has to offer!

Top guest favourite

Guest house in Pensacola

4.98 out of 5 average rating, 165 reviews

Private Guesthouse- 2 mi. downtown & 5 mi. Beach

Tucked away in the highly coveted East Hill area, this cottage has everything Pensacola has to offer. 1/1 on .5 acres. Space includes king bed & futon private driveway parking, courtyard & 2 patios with gas fire pit. Access to common spaces: wood burning fire pit, pergola dining & 2 kayaks! Close to downtown, beaches, shopping & dining. Walking distance to restaurants, coffee shops, & several parks. Whether you are in town for business or here for a vacation you will love this little charmer!

Guest favourite

Home in Navarre

4.96 out of 5 average rating, 102 reviews

Kokomo Key on Navarre 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!

Top guest favourite

Guest house in Milton

4.99 out of 5 average rating, 147 reviews

Charming Bayou Bungalow near downtown Milton!

Visit historic Milton while staying in our comfortable bungalow, which is close to everything making it easy to plan your visit. Nearby downtown boasts music, festivals, breweries, restaurants and farmers markets. Ride on site bikes on Blackwater Heritage Trail. Explore Marquis Bayou and Blackwater River in on site kayaks. Pick blueberries in season. 40 mins to Navarre Beach. 30 mins to Pensacola. Kitchen w/fridge/micro/toaster oven/dbl burner cooktop. Queen bed with comfy Serta mattress.

Top guest favourite

Flat in Pensacola

4.99 out of 5 average rating, 139 reviews

Serenity on the Bay-Waterfront attached studio

If you're looking for a quiet, get-away directly on the water, and convenient to everything, this is your place! Enjoy beautiful sunrises and gorgeous evening colors in this lovely waterfront studio. You will have a private hot tub steps from your room looking out over the bay. Direct access to a private dock along with two fishing poles and paddle boards upon request. Minutes to historic downtown and 20 minutes to the Gulf of Mexico and Pensacola NAS. this is an adult only property, 21+

Guest favourite

Houseboat in Fort Walton Beach

4.94 out of 5 average rating, 107 reviews

Unique water front stay Houseboat Destin/FWB

Seas the Day, center on Ft. Walton Beach,quiet bayou connected to bay and gulf on private 1 acre residence. We are 1 of only 3 HB for 50 miles in area. Paddle boards, kayaks , fishing poles and outdoor fire pit. Car needed to get to white sand beaches (4 miles). Shopping close by. A comfy futon in for a second bed. Boat has AC and heat. Unit is to stay docked.Recently renovated inside and out . Larger deck area with loungers . New lighting and ceiling this past spring! Rare find

Guest favourite

Townhouse in Navarre

4.97 out of 5 average rating, 156 reviews

Surf Shack Island Retreat

SNOWBIRD SPECIALS! Welcome to the Surf Shack Island Retreat. This home offers Santa Rosa Island Living, Sound views, short walking distance to pier, beach & sound. Completely remodeled and well equipped three story town home with multiple sleeping arrangements to accommodate groups up to 8. Ideal spot to getaway or space to work remotely, Plenty of space at 2,425 sqft. Private Master, en-suite and sitting balcony. PLEASE DO NOT BOOK IF YOUR GROUP IS LARGER THAN EIGHT

Top guest favourite

Home in Milton

4.96 out of 5 average rating, 190 reviews

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.