
Holiday rentals with a kayak in Clearwater Beach Island
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Top-rated rentals with kayak in Clearwater Beach Island
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House rentals with a kayak

Relaxing 4BR/3BA Getaway - Near Beach + Golf Cart
my family stayed at Leslie's place for Father's Day weekend, and we had a great time in her spacious, comfortable home. She really thought of all the details. I have two small children 3yo and 5 months old, and it was so nice to have toys, books, wipes, pack n play, and even a little balance bike available to use! so many amenities, the rooms were spacious and clean, the kitchen was well appointed, and a little basket of commonly forgotten things was such a thoughtful addition. really close to honeymoon Island. we will certainly stay again!

Waterfront Oasis
Had the pleasure of staying here for a few days. Nice quiet neighborhood and a very peaceful and relaxing time hanging out here. Would not hesitate to book again only next time would like to book a fishing trip on the Reel Anomaly docked out back. Just book it and enjoy.

*NEW* Riverside Retreat w/Pool
Everything was absolutely perfect! Beautiful and quiet neighborhood. The house was perfect to stay in, very cozy and spacious. Perfect spot for our home base when going to Universal for a day. The weather was perfect as well and being able to kayak down the river a bit was very therapeutic. Would love to come back again, especially to visit Tarpon Springs again. Love from Louisiana.

Luxe Private Waterfront Getaway with Pool in Ozona
Exactly the escape we wanted from the North East. The house was spacious and very comfortable with an amazing water view. I had coffee on the dock every morning. The owners were very responsive and ensured our stay was enjoyable Highly recommend.

The Weekender- Lake Access, Bikes, Outdoor Living
This place was absolutely amazing. From the moment I walked in, the house was clean and welcoming. Everything I needed was exactly where Kimberleigh said it would be. Kimberleigh has everything you could possibly need, from make up remover wipes to hair ties and straighteners in case you forgot your own. The home was sparkling clean and quite comfortable, with extra throw blankets and pillows. Every detail you can think of for a peaceful getaway has been executed. Kimberleigh, thank you for the clear communication and quick responses to everything and having such a beautiful getaway spot you’re willing to share with the world. I didn’t want to leave but I will certainly be back.

Amazing Private Beach Home
The house is very spacious all appliances in the house are up to date. Beds were very comfy and plenty of outdoor seating for watching the wildlife that cruises the shore line. We got to see the dolphins cruising in the bay along with flamingos and egrets and the pelicans. Neighbors are quiet and keep to themselves. Drive into Clearwater is easy and quick. Well worth the stay for the family getaway

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

Lakefront Paradise with Private Saltwater Pool
Very nice set up with plenty of activitys to do, Salt water pool was fantastic, Nice clean house Will definitly go back
Cottage rentals 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!

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

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 beach—very comfy and convenient with everything we needed. Lots of tvs, lots of space, easy to get around. I also liked having a fully equipped kitchen—only made dinner one night, but everything we needed was there! We’d definitely again and prefer it to the other resorts we have stayed at. It’s 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!

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.

Riverfront Home w/ Putting Green & Boat Dock!
Thanks for having us. Great location!

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. 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

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!
Destinations to explore
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- Anna Maria Island
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