
Holiday rentals with a kayak in Madeira Beach
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Top-rated Accommodation with a Kayak in Madeira Beach
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
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Holiday House Rentals with a Kayak

Lush Vacation Home with Pool
Our family of 4 enjoyed our stay. The house is updated with an open floor plan. TVs in each room, including the outside pool/kitchen area, beautiful kitchen. Highlights our family loved: private pool, nice lounge area, quiet community that was perfect for walking, close to amenities while being tucked away. Lissette was very responsive when we needed anything. And I loved the washer/dryer, which came in handy to keep up with pool towels.

Waterfront Luxury Retreat in Indian Rocks Beach
We had a wonderful stay at Graceâs 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!

Renovated peaceful 2 Bed cottage with/hot tub.
The house is just like the pictures. The kitchen has everything we needed and more. I would definitely would recommend this place.

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.

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!

Ocean Dream Villa| Beachfront with Private Pool
Great location for a large private house (but shared pool). While some of the inside feel a bit older, the location makes up for it. We had a couple minor issues but Mona was very responsive and was able to get things sorted out for us. Would stay there again.

Bungalow near the sea
Place was great. Very accommodating and pleasure to deal with. Thanks for everything!

Casa Paraiso- Pool Home with Canal Access
Very clean and comfortable bungalow with a stellar backyard area with lots of seating and places to lounge. Multiple tvs and a very fun game room, and three spacious bedrooms. Located in a great area with just two miles to Publix and other retail locations. The kitchen was fully stocked - could use a little love, as the silverware and cutlery were well used - and clean. The hosts are truly the hidden asset of this unit. Upon arrival, we learned that the previous tenant had broke the coffee pot. We asked Lorena about this on arrival and had a new coffee pot delivered in 90 minutes! Never had faster responses to any requests, and it was all positive. Very impressed and would stay again.
Cottages 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!

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike
Lisa was a great host, and paradise by the beach is an awesome place to stay. My family of 4 (2 adults and our older teens) just loved being able to have a lot of space (compared to the hotel rooms on st Pete beach) and a full kitchen and a close walk to the beach. The kids loved riding the bikes to get an ice cream at night, and it was so easy and convenient to pack up the chairs and umbrella and walk over to the beach. The walk is actually shorter than the resorts we have stayed at on spb. It was kind of like settling into our home by the beachâvery comfy and convenient with everything we needed. Lots of tvs, lots of space, easy to get around. I also liked having a fully equipped kitchenâonly made dinner one night, but everything we needed was there! Weâd definitely again and prefer it to the other resorts we have stayed at. Itâs less expensive, more convenient, and a lot more space. Thank you so much, Lisa! We hope your space is available next time we come down!

Sleep 7 Steps to Beach Pets OK Real Beach Cottage
Exactly as advertised, steps from the beach, wonderful cottage. Capt Al had plenty of instructions to explain any questions you would have. Tons of beach stuff to use too, towels, umbrellas, toys, chairs, etc. My wife, two girls and I had a fantastic time and would most definitely rent again.

Happy Camper Cottage | Cozy Oasis with Hot Tub
Anna was extremely helpful and accommodating for our last-minute trip with the kids. Her place was super cute and very clean and well kept and we would be happy to recommend it to friends and family or return ourselves. Thank you so much, Anna!

Sandy/Salty- Sleep 16 - 2 homes connected by yards
Great gathering place for an extended family to get together. Very short walk to a stunning beach Great for kids. Perfectly located next to a park as well which was great.

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. Sheâs very responsive to questions and even though she lives next door, never intrusive. Sheâs so gracious weâd be back in a heartbeat! đ Truly one of the best experiences weâve 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!
Quick stats about holiday rentals with a kayak in Madeira Beach
Total rentals
30 properties
Nightly prices starting at
$77Â AUD before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
- Adventure Island
- Splash Harbour Water Park