
Vacation rentals with a kayak in Anna Maria
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Top-rated kayak rentals in Anna Maria
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House rentals with a kayak

CANAL FRONT- Hot Tub-Dock-Kayak-Fish-Swim
James was an incredible host very responsive, the bed we very comfortable canal view with dolphins and manatees swimming by kayaks , a great hot tub which was used everyday of the trip and a nice big clean house the house does not look that big when you walk up but when u get inside very spacious would definitely go back

Waterfront, Beach, Pool,Kayaks near Islands, Parks
My family wanted to kayak, jet ski, swim, and hang out and Marco's place was perfect. We grilled burgers every day, had my cousin, niece and mother come for dinner and to check out the mangrove canal and pretty sunset. The jet ski rides out to the Gulf were a blast. Dolphins came up and swam beside us. Our adult daughters LOVED it. We saw all sorts of wildlife on the Anclote trails that is accessible from the house. We brought our bikes and rode the trails every day. Marco was an excellent host, fast response, and very knowledgeable about the area. The house is spacious and comfortable. We had a marvelous time.

Waterfront home with pool and Jacuzzi. Boat to bay
We enjoyed our stay in Tampa at Chris’s home. House was exactly as described and in pictures. The pool and hot tub was a great addition. Chris was very responsive and accommodating. We enjoyed our short visits from Joseph the cat and friend .

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!

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach
Family drove in from all over for our son’s 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.

Waterfront Oasis! Kayaks,Hot Tub
Peacful hot tub, easy access kayaks, relaxing atmosphere for living room and kitchen. It felt very homie, like i was at a friends house. Decor was very warm and inviting. We truly had a blast and got some GREAT! R&R. Beds were super soft. It was like sleeping on a cloud

Bungalow near the sea
Jeff is great with communication, location is fantastic very close to everything!

Tree House Treasure
This Treehouse oasis was an absolute delight tucked away from the hustle and bustle! Having a quiet home with a full kitchen as opposed to a hotel room sold us, but having a canal leading to Lake Tarpon, kayaks, super comfortable platform king bed, peaceful neighborhood full of native critters and foliage, and walking distance to Anderson Park were all icing on the cake! We hope to be able to return in the future. Thank you, Nancy❤️
Cottage rentals with a kayak

Pink Gulfside Cottage, Steps to Beach, Pets OK
This was our second stay at Clearwater Cottages and it was just as great as the first. We love the old Florida charm and it is in a great location that is walkable to the best restaurants. Also walkable to many bars and shopping. The free parking is nice too. As he mentions in the listing, the building is older and has some quirks, but the cottage is adorable and you really are steps from the beach. We also love that we can bring our dogs and the location is near the dog friendly part of the beach. It was a great stay!

Anna Maria Cottage w/Golf Cart
Our stay was great. Having the Golf Cart was so handy we didn’t have to rent one. The house is nice and clean the bedding towels. Everything was nice and clean. We would definitely stay again.

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
If you're looking for a peaceful retreat, you'll find it here. We had an amazing experience at the Lazy Gator ! Cottage is equipped with everything you could need, including alligators that swim by and bass jumping out of the water. We would definitely return. Thanks Josh!

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!

Alafia River Cottage
The Alafia River House did not disappoint. Check in was easy with helpful photos & directions. The neighborhood is pretty quiet but yet close to everything too. The house is tucked in right on the river, the yard is lush & Florida tropical, it is the perfect place to sit & read, eat a meal or take a nap. Watching the chickens and surrounding nature are an added bonus. The home is old with character, but so clean & refreshing. All the things you need and more are carefully stowed in antique furniture. Martha is easy to contact, but you shouldn’t need anything. The kitchen is up to date & has all of the extra things that you probably forgot to bring. My husband and I had a sweet trip & the Alafia River House was a gem. Thank you Martha.

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

Kayaks, Fire pit, gated community - The Getaway
Comfortable place in a gated community which made us feel safe. Plenty of shopping and restaurants around the area. Suzanne messaged us during our stay to make sure everything was going well. Thank you Suzanne.
Quick stats about vacation rentals with a kayak in Anna Maria
Total rentals
20 properties
Nightly prices starting at
$130 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
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Clearwater Beach
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Jannus Live
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