Vacation rentals with a kayak in Pensacola Beach

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Top-rated kayak rentals in Pensacola Beach

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Guest favorite

Apartment in Gulf Breeze

4.97 out of 5 average rating, 143 reviews

Redfish Loft, private waterfront Apt. on East Bay

Light airy open floor plan " pet friendly " 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, quiet neighborhood. Join us @ Fire pit that is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

Jan 7 – 14

ﺩ.ﺇ518 per night

Guest favorite

Bungalow in Pensacola

4.96 out of 5 average rating, 117 reviews

May & June! Red Door Bungalow Downtown Sleeps 6!

Ready for Spring or Summer Vacation in Pensacola! Love the charm of an older home, but require the comforts of a modern one? Welcome to our cozy Red Door Bungalow! This quaint home is half a mile from the center of downtown Pensacola. Local restaurants, Blue Wahoos stadium, shopping, parks, and night life are around the corner. 10 mins from NAS. 15 min to the beach. Park and playground are located right across the street. This home is perfect for that quick getaway or mid-term stay! DM questions

Sep 5 – 12

ﺩ.ﺇ382 per night

Guest favorite

Condo in Mary Esther

4.87 out of 5 average rating, 131 reviews

Waterfront Condo with FREE Kayaks

* Right on the waterfront ! *Free Kayaks ($300-$400 value as the same kayaks rent for $ 100/day /kayak) down the road at the rental place. The place is right in front of the water with amazing views of the Santa Rosa sound and Okaloosa island, the pool is 5 steps away. *Large and airy one bedroom, one living room, kitchen and bath, TV in both rooms. Endless summer days at its best. *Kayaks are free to use. *We are 4 miles to the Gulf beach on Okaloosa Island and 9 miles to Destin Harbor.

Jan 16 – 23

ﺩ.ﺇ361 per night

Guest favorite

Camper/RV in Navarre

4.92 out of 5 average rating, 108 reviews

The Camper Retreat with kayaks and 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.

Oct 17 – 24

ﺩ.ﺇ431 per night

Guest favorite

Place to stay in Pensacola

4.9 out of 5 average rating, 188 reviews

Our House Yall's House

5 Miles from 2 I-10 ramps, 25 mins to NAS, 30 mins to 2 different beaches - Pens Bch & Perdido Key, 3 miles to equestrian, 4 miles from NFCU. We have a private entrance, walk-out basement. There are other bedrooms if necessary; however, those would be in our living space & more $$. We can accommodate up to 6 guests. During warmer months, pool and tiki are beautiful, another open patio and outside cooking - grill. Area inside has microwave, coffee pot, refrigerator, toaster oven, 52" t.v.

Mar 3 – 10

ﺩ.ﺇ402 per night

Guest favorite

Guesthouse in Milton

4.99 out of 5 average rating, 113 reviews

Charming Bayou Bungalow - walk to downtown Milton!

Enjoy visiting historic Milton while staying in our comfortable cottage, which is close to everything making it easy to plan your visit. Walk to downtown Milton for live music, festivals, breweries, restaurants. 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 New Queen bed with comfy Serta mattress.

Aug 9 – 16

ﺩ.ﺇ368 per night

Guest favorite

Condo in Pensacola Beach

5.0 out of 5 average rating, 112 reviews

Stay at Sunshine Daydream on Pensacola Beach

Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

Mar 19 – 26

ﺩ.ﺇ1,079 per night

Guest favorite

Condo in Pensacola

4.96 out of 5 average rating, 146 reviews

Comfy 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 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!

Sep 23 – 30

ﺩ.ﺇ331 per night

Guest favorite

Townhouse in Pensacola

4.91 out of 5 average rating, 122 reviews

Serenita Ora: Quiet Waterfront Unit with 2 Kayaks!

Welcome to Serenita Ora! Come enjoy beautiful views, coffee on the balconies, and the peaceful waters. Our oasis sits directly on a calm, private, shallow cove of Perdido Bay, providing the perfect place for families to play safely. This 2 bed/2.5 bath sleeps 5-6 and includes a fully stocked kitchen, laundry, and 2 Kayaks! Spend all day right here enjoying the quiet serenity, tucked away from the hustle and bustle. Or take a short 5 minute drive to Perdido Key Beach, restaurants, etc.

Oct 29 – Nov 5

ﺩ.ﺇ712 per night

Guest favorite

Townhouse in Pensacola

4.92 out of 5 average rating, 286 reviews

Townhome A w/hottub in downtown, mins to beach

Pet Friendly! Each side Sleeps up to 6 or rent both sides to accommodate 12 with advanced notice. Blocks from historic Downtown Pcola. Restaurant’s/activities/entertainment minutes away. Fenced in backyard, deck/Hottub/outdoor shower, bikes/grill/firepit. Several parks in walking distance including the Bayfront. $100 (per) pet fee paid directly to the host after checkin. 10 min drive to Pcola beach. 24ft boat/w Capt available for day inter coastal excursion, no fishing

Aug 9 – 16

ﺩ.ﺇ610 per night

Guest favorite

Guesthouse in Navarre

4.95 out of 5 average rating, 215 reviews

S.K.I. Beach House (Spending our Kids Inheritance)

One of the new houses on the beach. Where you have beautiful views of the sunrise over the Gulf from your front deck and the sunset over the Santa Rosa Sound from your back deck. You are just a short walk to amazing shelling, swimming, paddle boarding, kayaking, boogie boarding or just plain relaxing on the "Most Relaxing Place in Florida." All on the sugar white sand beaches of the Emerald Coast. During your stay here you will find yourself in a suite full of amenities.

Nov 5 – 12

ﺩ.ﺇ689 per night

Guest favorite

Townhouse in Gulf Breeze

4.94 out of 5 average rating, 109 reviews

Gulf Breeze Your own private resort on the bay!

Best sunset's in Pensacola area. A place where you can watch for dolphins, fish off the dock, pull your boat up, take the kayak out. lay under your own pergola with lounge chair's. Listen to the waves while lying in the hammock watch the pelicans crash land in the bay. grill on the deck . have a picnic. swim off the dock , lay in a raft. Fire Pit , corn hole game in garage,1400 square feet with accommodations for 6. 3 bd/ 2.5 bath 3 mile's to Pensacola beach .

Jan 8 – 15

ﺩ.ﺇ594 per night