
Vacation rentals with a kayak in Gulfport
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House rentals with a kayak

Waterfront Luxury Retreat in Indian Rocks Beach
We had a wonderful stay at Graceās place for our annual girls trip to spring training. The house was amazing, very clean and modern. Stocked with lots of conveniences. Great place to make group meals and chill out. Slept all 8 of us comfortably. The water views were spectacular. Very walkable to the main road where there are some restaurants and ice cream. We had everything we needed!

Silverking Keys Retreat!
Excellent spot for fishing, going out into the bay, and enjoying the water. We brought our boat and jet skis. A close-by ramp. Place was very clean and updated. Soothing views at night from the dock. Wayne is a fantastic host and super friendly, responsive and great at offering local suggestions. Heās the one that gave us the recommendation for the closest ramp. Overall, a fantastic stay.

Casa Coquina: waterfront, pool, hot tub, boat lift
Loved the house! Pool! and Location on the bay! The pictures were very accurate and Jilla contacted us to make sure everything was going well and to see if we had any questions the first evening. It is a very thoughtful setup, such as, speakers throughout the house and an app to control them as well as lighting throughout the house and outdoors. It was a short drive to St. Petersburg (restaurants/breweries) or Tampa (ball game), however not much in walking distance but we knew and wanted that. Everything was great! We wish we could have e stayed longer. - thanks for everything.

Saltwater Retreat, 3 minute walk to Gulf beaches!
Hannah was a wonderful host very helpful, kind, and quickly answered any question we had! Her husband was very nice and offered tons of recommendations of good places to eat. We were able to walk across the street to the beach within minutes and thereās lot of restaurants nearby. Also really enjoyed the back porch and beach supplies provided. The kitchen was well equipped with everything we needed to make a meal & inside is exactly like the pictures and offers an especially cozy home-y vibe. Would highly recommend if your considering staying at here :)

Ocean Dreaming: Waterfront Home with Heated Pool,
We would go back in a heartbeat! The house and location was perfect! Our kids loved the pool and being able to kayak and paddle board right from the dock was amazing! We saw dolphins multiple times a day and had fun fishing. The golf cart was perfect for getting to the beach and plenty of restaurants, including an ice cream shop! I would totally recommend this place!

Waterfront Duplex- kayaks, SUP, 3 blocks to beach
We booked this Airbnb for a girls' trip and after comparing a few places in the area, weāre so glad we chose this one! The location is fantastic. Just a short walk to the beach and a quick drive to the busier spots like Clearwater with restaurants and nightlife. The home is tucked away in a quiet area right on the bay, which made for a peaceful and relaxing stay. It is a duplex, so some of the outdoor amenities are shared with neighbors, but that was never an issue for us. Everything was thought of to make your beach trip great, including wagons, chairs, and coolers. Everything was clean, comfortable, and exactly what we needed for a fun and chill getaway. Would definitely stay here again!

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach
Family drove in from all over for our sonās graduation from USF and everyone was extremely pleased with the accommodations. We really enjoyed the lower level game room, the kayaks, the pool area, and the local restaurants - notably the ice cream shop across the street! The elevator was a big plus as well. Everything ran smoothly, the house was well stocked with essentials, and everything we used worked perfectly fine. We thoroughly enjoyed our stay.

Dolphin Blue Beach House-Waterfront, Pet friendly
I can't recommend this house enough! My wife and I stayed here for honeymoon, and it was comfortable, felt very cozy, and had a great view of the West Coast Intercostal. The deck chairs and hot tub were great to relax in. The location is also nice - minutes away from the beach, restaurants, and boat rentals, and about a half hour drive from Tampa and St. Pete. Deanna was very helpful and communicated well.
Cottage rentals with a kayak

Sunny PaG Island rental w/bikes-just steps2beach
Great place right on Pass-A-Grille. Far enough from the restaurants to be quiet, but close enough to walk/stumble to. Beach access is very close. Parking as easy as possible. Rental was Clean and Plenty of Amenities. Would stay again.

Pink Gulfside Cottage, Steps to Beach, Pets OK
Great old school beach cottage. Perfect for my Son and me. The Capt. and especially the First mate made it 5 stars!

Little Manatee River Cottage
Had a great stay ! Fishing was fun and right across the street Would stay again for sure !

Hot tub, 2 floors riverfront, Bush Gardens, kajaks
Cozy, comfortable, yet two stories with plenty space to stretch out, scenic view with a hot tub, nice balcony view for coffee in the morning. Canāt go wrong.

Cozy Cottage - Nature Lovers Dream - Horses - Lake
Dave and Lindsay gave us our space, but were quick to respond when I had questions. My kids enjoyed giving the horses carrots. I would def stay here again. Highly recommend.

Elegant Crystal Beach cottage within sea glimpse
This super cute cottage is very clean with up-to-date appliances and beautifully decorated with well-thought-out use of space! We stayed for 10 weeks and slept soundly every night due to the comfortable mattress, peaceful & quiet safe neighborhood. The newer fixtures and large washer/dryer were so convenient. Communication with Mary Jane was fantastic. Sheās very responsive to questions and even though she lives next door, never intrusive. Sheās so gracious weād be back in a heartbeat! š Truly one of the best experiences weāve had in the nearly decade of staying in Airbnbs. Location is a bonus as is very walkable to Bay/Beach or bicycle to the Pinellas Trail. This area has so much to offer with beaches, trails, restaurants, fairs, etc

1 Bd Immaculate Gulf front BOHO Beach Cottage
Just as the pictures show this is a super cute cottage as close to a beautiful stretch of beach as you can get. Cottage was squeaky clean and appointed with everything you need for feeling right at home. The back patio is wonderful with shade, ocean breezes and the wonderful sound of breaking waves. The little path to the beach is right off the patio. Would stay again in a heartbeat!

Escondido Boutique Bungalow in Crystal Beach
Truly immaculate place. If you are in the crystal beach/ palm harbor area this is the place. Period. It was BEAUTIFUL. One of the cleanest Airbnbs I've ever stayed in, comfy bed, private and secluded which was ideal for a couple. LOVED it. The hammock swings were a plus for me. Just felt nice to have an atypical lounging space. Very close walk to peaceful sunsets. Susan and Mark were helpful and fully responsive. Thank for the beautiful memories I'll have from being here!
Quick stats about vacation rentals with a kayak in Gulfport
Total rentals
20 properties
Nightly prices starting at
ļŗ©.ļŗ147 before taxes and fees
Total number of reviews
660 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park