Vacation rentals with a kayak in Holmes Beach

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

3/3 condo with Pool - 2 miles to beach

Our Happy Place is a stylish 3-bedroom, 3-bath condo in the exclusive Margaritaville – One Particular Harbor at Harbour Isles. This spacious retreat features a fully stocked kitchen with island seating, a dining area for six, and a cozy living room that opens to a screened balcony with serene lake and nature views. Each bedroom offers comfort and privacy, with two en suite baths and thoughtful touches like remote-controlled ceiling fans and blinds. Guests can enjoy community amenities including

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Waterfront Pool Oasis •Kayak, Games & Sunset Views

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

River House with Kayaks. Relax on the River.

Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

Discounted October Stays w/Private 30' Dock & Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Waterfront Retreat | Pool • Spa • Dock | Bridge St

🌴 Anna Maria Island Waterfront Oasis! Private dock + heated pool included. Relax by the pool, sip coffee on the dock, or walk just 5 minutes to the Gulf’s sugar-sand beach. Bright, updated home with stocked kitchen, fast Wi-Fi, smart TVs, and cozy beds—perfect for families or couples. Grill by the pool, dine outdoors, or fish from the dock. Boat/kayak friendly. Beach gear + parking included. Your peaceful island escape awaits.

Las Palmas Beach Rentals unit 2

Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

Manatee Retreat B

Our newly renovated home sits on a beautiful canal and has access for kayaks, and other fun water activities. Sit on the patio or in the screened porch and watch the manatees play and the mullet jump. We are tucked away in our private oasis. It's only 206 steps to the beach. Easy walk to shops, bars and restaurants. Each bedroom has a queen bed, plus a pull-out couch in the living room for an additional bed.