Waterfront holiday rentals in Lido Key

4.88 out of 5 average rating, 121 reviews

Home in Longboat Key

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

5 out of 5 average rating, 3 reviews

Condo in Bradenton

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!

5 out of 5 average rating, 42 reviews

Home in Bradenton

Dreamy Waterfront Bungalow w/Priv Dock & Swim Spa

Boater’s Paradise on Warner’s Bayou! Bring your boat or jet skis and tie up at your private dock. Watch dolphins & manatees from the patio or relax in the heated swim spa after a day on the water. Just minutes from public boat ramps, Robinson Preserve, and the beaches of Anna Maria Island, this peaceful retreat offers the perfect mix of adventure and relaxation. 🚤 Bring your boat or kayak! 🌴 5 mins to Robinson Preserve 🏖️ 10 mins to Anna Maria Island 📶 Fast Wi-Fi | Smart TV | Onsite laundry

5 out of 5 average rating, 21 reviews

Home in Port Charlotte

Modern Waterfront Bliss

Bring the whole family to this exceptional canalfront gateway with lots of room for fun. Brand new, spacious retreat nestled along the peaceful canal. This modern home is designed for both comfort and style, offering cozy interiors and expansive living spaces perfect for relaxation. Whether you're enjoying the serene water views from the patio, cooking in the fully equipped kitchen, or unwinding in the beautifully appointed bedrooms, every corner of this house invites you to feel right at home.

4.89 out of 5 average rating, 9 reviews

Home in Port Charlotte

#1 Amazing Waterfront Home w/pool - Prime Location

Beautifully fully furnished waterfront home with pool, dock, and all the amenities! You'll enjoy the private, screened lanai with room to dine next to the pool with cascading fountain or soak up the sun in the lounge chairs while viewing the canal. Sleeps 6 comfortably. Gorgeous spacious master bedroom with master bath, two walk-in closets, jacuzzi tub and walk-in shower. Close to many restaurants, shopping, fishermen's Village and all Punta Gorda and Port Charlotte has to offer.

4.94 out of 5 average rating, 51 reviews

Holiday home in Ruskin

No Damage Waterfront Townhome at Little Harbor

Come enjoy yourself at our townhome. Relax with the whole family at this peaceful place to stay with four private balconies. Our townhome is located in the seaside village of Little Harbor with a white sand secluded beach, two waterfront restaurants, seaside pool, tennis courts, fishing piers, watersports rentals, two onsite marinas, and much more. Enjoy watching the fish jump and the many varieties of birds in the natural preserve framed by the canal from your private balconies.

4.93 out of 5 average rating, 107 reviews

Townhouse in Ruskin

Still Waters Townhome, Sunrise and Sunset Views

Elegant home with 4 balconies, 2 overlooking water. Sunset and sunrise views. Gourmet kitchen, granite countertops, cooktop range, stainless steel appliances. Coffee maker, tea kettle, Nutra-bullet, toaster and more. Each room has a large flat screen smart TV. Bright, modern, immaculate. Wireless internet, Ethernet and Netflix. Washer and dryer on main level. Five minute walk to white sand private beach, complimentary umbrella and chairs. No smoking, no pets, no events.

4.89 out of 5 average rating, 118 reviews

Condo in St. Petersburg

Waterfront Condo w/ heated pool- near Fort Desoto

100+ raving reviews! This waterfront condo features a private balcony nestled next to the mangroves and shoreline with breathtaking water views. There is a full kitchen, king bed, a queen memory foam pullout sofa all waiting for you to enjoy. The resort like complex is located in the well desired Tierra Verde and features a waterfront heated pool and hot tub, observation pier, boat dock, and more! Only a short drive from Fort Desoto, Pass-A-Grille, and St. Pete Beach.

4.89 out of 5 average rating, 35 reviews

Home in Ruskin

Waterfront Home w/ guest house!

Relax with the whole family at a peaceful waterfront vacation house w/ a separate guest house! This is a retreat to relax, & soak up the sun! Enjoy a pool table, dart board, putting green, kayaks, pool & hot tub while listening to the sound of a cascading waterfall. This spacious property is on a canal just outside the nature preserve & Tampa Bay. Your own boat ramp & two boat docks! 30-min drive to Tampa & St Petersburg, with many beaches nearby!

4.95 out of 5 average rating, 22 reviews

Home in Port Charlotte

The Waterfront White House

BRING YOUR BOAT🤙🏼 Our three-bedroom two-bathroom home nestled on a canal leading to the Charlotte Harbor, is one you won’t want to miss. Newly renovated, with room to stretch out in, plenty of parking, the place is just as cozy as it looks. The boat dock has 2 underwater fish lights that bring in everything from snook, to redfish, to tarpon, and the boatramp is only 12 minutes away. Come enjoy water front southern living at its finest.

4.91 out of 5 average rating, 113 reviews

Cottage in Ruskin

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.