Holiday rentals with a kayak in Sarasota Beach

Intracoastal Connections-Incredible Sunsets-Luxury

Experience waterfront luxury at this stunning 3-bed, 3-bath gem in Marina Walk, One Particular Harbor. Just 1.8 miles from Anna Maria Island's beaches, this home offers breathtaking views of Anna Maria Sound. Monthly guests enjoy resort pools, fitness center, nature trails, kayaking, and Sky Bar. Short-term visitors access the pool, splash park, and BBQ areas. Relax on the lanai, savor sunsets, or explore local attractions. Fully equipped with beach essentials, it’s your perfect coastal escape!

Minutes to Sand, Dog Friendly, Hot Tub Luxury

Watch the stars from your hot tub! Not camping, not glamping... This is luxury living for less! Private dog friendly property. Hooked up to city water, cold air in all rooms, immediate demand hot water and septic. This slice of paradise is minutes from the sand and has an elegantly appointed private master, two private loft bedrooms, sleeper sofa & 9' vaulted ceilings. Your private retreat includes the use of two kayaks, gazebo, beach chairs, 5G Wi-fi & Netflix, Prime, Paramount. Paradise!

Silverking Keys Retreat!

Come stay and play at this beautiful 2 bedroom 2 bathroom house (only 1st story) located right on the Tampa Bay! It faces downtown Tampa and St. Petersburg. You can cook breakfast and view the bay straight from the kitchen dinette. The property is located on a dead end street. Fish, and star-gaze from two private docks, one being a two-story. Fish, kayak, snorkel, and you can bring your own boat! A natural sanctuary for dolphins, manatees, red fish, blue herring, snook, ospreys, and eagles!

Free Kayaks/bikes/walk to beach/pet friendly #3

"Perfect for family / friends/pets, who want to escape the stress into paradise on Manasota Key. One block from beach. 1 bed 1 bath beach cottage 1st floor has great spaces, king size bed/ queen sofa bed, full kitchen, private lanai, electric grill/ garage/laundry area/free bikes/kayaks/ that you can enjoy at the beach or the bay. Great restaurants/bars/trails and much more just walking distance from the house. Beach toy, chairs/umbrellas/snorkeling gear included. Just come relax and enjoy.

The Manatee Flat at ManasotaKeyHouse 2bed/2bath

* Due to recent hurricanes, Manasota Key sustained heavy damage. Our property had minor damages (being on stilts), but repairs have been completed. We are excited to be renting again! Businesses and home owners are working hard to recover and rebuild. Things are constantly changing on the island, with various closures. What is mentioned or pictured in our listening is not accurate due to the constant changes. We will do our best to keep our guests up to date. Manasota Beach is open!

Serenity with Kayaks Fishing Beach Gear & Sunsets

Escape to tranquility and experience the magic of life on the water. Whether you're seeking relaxation, adventure, or a bit of both, we welcome you with open arms. Let the gentle waves, fresh sea breeze, and waterfront views create the perfect getaway. Living the dream has never been this easy! Come aboard and make unforgettable memories. ⚓ 📢 Special Offer: * First two nights—No cleaning fee! * After three nights—$75 cleaning fee applies. Book your stay and let the adventure begin!

Riverfront Tiny house W/Kayaks

Get away from it all when you stay under the stars in this riverfront tiny home with queen bed.This 10x14 Tiny house is located directly on Horse Creek/Peace River. The perfect place to escape to nature. The 10 + acre property has kayaks and Canoes as well as a boat ramp if you want to bring your own. Enjoy the peaceful wildlife, have a bonfire and fish out your backdoor. No indoor smoking and no animals. We are a farm, so we cannot allow outside animals to the property.

Good after Milton -Kayaks & Steps to Beach sa

Great news! We've reopened after Milton! 3 Restaurants, stores, our beach access & Stumpy's Free Ride now open! In a prime Manasota Key location, our talented interior designer created this beach bungalow gem with 2 bedrooms, Tv's & kitchen with dining set. Walk only 1 minute to delightfully uncrowded beach! Swim Spa with waterfall & massage therapy jets in common area. Free kayaks. Login to your favorite streaming service with Smart TVs.

Little Manatee River Cottage

This cottage is located on the Little Manatee River. Sun City Center 10 min Aquatic rentals walking distance. The cottage is updated. Abundant fishing charters, Little Harbor, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets out on the river, on the dock or at Little Harbor sipping your favorite drink.