Holiday rentals with a kayak in Longboat Key

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Casa Rosa~beautiful waterfront~steps to the beach!

Welcome to Casa Rosa - centrally located - 5 houses to the beach, walk to town/Bridge St or kayak/boat from your own dock/heated pool! Every morning, you can watch the sunrise, dolphins and boats go by from the 2nd floor porches. In the afternoon, take a quick 5 minute walk to play at the beach or watch the sunset! Are you competitive? We have ping pong, pickleball and kayaks to exude your energy! Want to just relax? Hang out by the pool, snuggle on the large sofa, or relax on the porches

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach

Apollo Beach Waterfront Pool Home, 4 bedroom-4 private baths & elevator. Theater room-murphy bed (5th bedroom). Game room- pool, air hockey.. Enjoy kayaks, paddle boards, fish at the dock, book a boat charter with owner. 3 restaurants, Bakery, Cigar Bar and Coffee/Ice Cream-walking distance. Apollo Beach - 1/2 mile away! Bahia Beach -2 restaurants and EG Simmons Beach - 20 min away. Bring your boat, dock at house, Apollo Beach Marina - 2 min. away. Animal-free home due to severe allergies.

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.

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Welcome to your island beach escape! This charming coastal abode boasts all the island vibes you need for a relaxing getaway. Enjoy the quaint historic village (5 houses wide) while being just steps away from the most beautiful beach in Florida! Take a stroll through the picturesque streets of Pass A Grille and soak up the old beach charm. The rental home has hardwood floors, a screened-in porch, and a sun patio, 2 bikes to cruise around the area! open-concept kitchen + bar and smart TVs.

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Pet fee $50.

*New* Waterfront Retreat: Pool, Spa, Dock & Views

*Brand New Listing from a Superhost* Experience elevated canalfront luxury with breathtaking views, a private pool, spa, and modern, stylish design throughout. Lounge by the pool, unwind in the spa, or paddle the canals with provided kayaks. Minutes from Apollo Beach’s beaches, waterfront dining, and lively local spots. Bringing a boat? Enjoy direct Tampa Bay access from your private dock. A perfect upscale waterfront escape for couples and friends.

Waterfront Duplex- kayaks, SUP, 3 blocks to beach

☀ Bay Views ☀ Shared Hot Tub ☀ Dock with Stand-up Paddle boards, Kayaks, Bikes ☀ Only 3 blocks to the sugary sands of Indian Rocks Beach ☀ Duplex- book independently or together ☀ Blackstone, 6 burner Charbroil Grill ☀ 10 Foot Custom Wood Bar w/ Jenga, Giant Connect 4, Corn Hole, Ringtoss ☀ Beach Wagons, Speaker, Zero Gravity beach chairs, beach towels, cooler ☀ Amazon Dot with Unlimited Amazon Music