
Holiday rentals with a kayak in Anna Maria
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Top-rated Accommodation with a Kayak in Anna Maria
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Holiday House Rentals with a Kayak

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool
Stop what you are doing and BOOK THIS PLACE!! Clean and spacious home ✔️ Fully stocked kitchen (pots, pans, glasses, condiments, spices, etc) ✔️ Tons of amenities like hot tub, fire pit, egg chairs, hibachi grill, golfing area, etc ✔️ All the beach equipment that you need (chairs, tent, snorkel, masks) ✔️ PLUS the best Host who was always quick to respond to any questions and even installed a new thermostat while we were there because the old one was messing up the temp and we like a cool 70 degrees at home ✔️ And if that wasn’t amazing enough, the host also took us on TWO BOAT TRIPS!!! All we paid for was the gas and any drinks or snacks that we wanted to bring (plus a tip since the boat tours were the highlight of the trip). Vlad knew all the best spots for private island time, snorkeling, and dolphin watching!! In all honesty I spent a fair amount of time trying to decide if I wanted to write an accurate review or gatekeep this hidden gem… I decided not to gatekeep.

The Pink Riverhouse- No damage from Hurricanes
Our stay at Katie's was a wonderful experience. So much to do within the house as well as the backyard. Katie & Terry were both prompt when needed throughout the trip and made us feel at home. Katie also have great recommendations for grocery shopping which made me fall in love with the Amisb Supermarket. Also, great proximty to many attractions. We will most definitely find more time to stay here again!

Poolside Chill & Grill, Hot Tub, & Fun Games!
Carol was such a great host! We had a few questions throughout the stay and she was quick to respond. The space worked out for the 11 of us. We appreciated all the amenities (grill, pool toys, beach supplies, lots of beach towels, etc) and had a great time in the pool. Kids loved all the other activities as well, especially the ski ball.

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach
This house was perfect in every way!!!! I have two handicapped parents and was able to bring them thanks to the elevator. The pool was great for the kids but the game room was the real winner here. There was something for everyone in this house. It was spacious so we didn’t feel as if we were on top of each other. Would gladly stay here again and highly recommend this house for a family getaway.

Apollo Beach Waterfront Amazing PoolOasis w kayaks
This was the perfect place for a nice, peaceful long weekend. The house was perfect. Spacious and extremely clean, the pool was perfect and a nice was to relax after a day of outside activities. Love the tv on the back porch. Our last day we fished off the dock then grilled and hung out in the pool while watching a movie. It was so relaxing. Fishing was good as long as you had an outgoing on incoming tide. Caught a variety including trout. Publix and everything else you need is literally a couple miles away, but you are still in a very quiet neighborhood. The hosts were amazing. I’ve never had host respond as quick as these hosts did. They weee very helpful. The first pan is to stay here again and this time bring a boat with us. I can’t think of one negative thing to say. Everything was perfect!!

AMI Cortez Beach Retreat Poolside Resort-stylePool
It’s a perfect little spot for a family we enjoyed it felt like home , it’s a perfect T combo for a beach day and pool day at the same time , we enjoyed it very much , we will definitely recommend the area it’s great

Urban River Edge Loft w/Soaking Tub and King Bed
We stayed one night and had a great experience! John was very communicative and made sure everything went smoothly. The host created a welcoming atmosphere with relaxing, easy-listening music playing when we arrived, which really set the tone. There was plenty of space to park our jet skis in the driveway, which was a huge plus. The home was stylish, comfortable, and thoughtfully arranged…perfect for a quick getaway!

Relaxing Escape, Pool, 3 BR, 8 miles to AMI
Perfect stay Trysten’s place was super nice and clean it was an awesome weekend with my friends and his communication is amazing and will walk you through every process definitely worth the stay and would 100% book again.
Cottages with a kayak

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!

Anna Maria Cottage w/Golf Cart
My son and I had a wonderful stay at this cute little cottage. Everything was clean and well-decorated, and we had everything we needed in the kitchen. We loved having the golf cart to run around in! The host also provided beach chairs and a kayak to use, which was very handy. The area is pleasant, situated in a quiet neighborhood with public tennis and basketball courts across the street. Anna Maria is a happy little island, with a lot of good food and entertainment, and a number of beach areas to choose from. Lynda was very responsive to any questions we had, and provided a lot of easy -to-follow instructions for the house, as well as lots of helpful tips about the area. We will definitely be back!

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. Can’t go wrong.

2/2 Charming Riverfront Cottage w Deck & Kayaks
We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️

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.

Alafia River Cottage
This place was wonderful ! Martha was great and very responsive anytime ! Quiet and peaceful and very charming cottage ! Will definitely be returning

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. She’s very responsive to questions and even though she lives next door, never intrusive. She’s so gracious we’d be back in a heartbeat! 💗 Truly one of the best experiences we’ve 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
Quick stats about holiday rentals with a kayak in Anna Maria
Total rentals
20 properties
Nightly prices starting at
$201 AUD before taxes and fees
Total number of reviews
840 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
20 properties have a pool
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen 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
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park