Waterfront vacation rentals in Siesta Key

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Top-rated waterfront rentals in Siesta Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Superhost

The home's exterior is softly illuminated by warm lights, highlighting the paved driveway and tropical landscaping. Tall palm trees and lush greenery surround the entrance, creating a serene atmosphere. The modern roof adds a contemporary touch, enhancing the inviting appearance of the property.

Home in Longboat Key

4.88 out of 5 average rating, 120 reviews

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

Superhost

Condo in Bradenton

5 out of 5 average rating, 3 reviews

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!

Top guest favorite

A modern canalfront home is showcased, featuring a well-maintained lawn and palm trees. The exterior presents a combination of light-colored walls and a dark roof. Large windows allow natural light into the living spaces, while a spacious driveway leads to the double garage.

Home in Port Charlotte

5 out of 5 average rating, 21 reviews

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.

Top guest favorite

An aerial view showcases the waterfront retreat with a private boat dock and spacious outdoor areas. The property is surrounded by lush greenery, and the tranquil Bayou waters reflect the clear sky. A nearby boat launch is visible, enhancing accessibility for water activities.

Home in Bradenton

5 out of 5 average rating, 41 reviews

Dreamy Waterfront Bungalow w/Heated Spa. Near AMI.

Charming WATERFRONT retreat on Warner’s Bayou with a private boat dock right outside your door. Enjoy stunning waterfront views and frequent visits from dolphin and manatees. The fully equipped kitchen, spacious living area, and cozy bedrooms will make you feel right at home. Unwind on the patio or soak in the heated swim spa. Explore Robinson Preserve or take a short drive to Anna Maria Island for sun, sand, and adventure—just minutes away. Your unforgettable Florida escape starts here!

Guest favorite

Condo in Tierra Verde

4.72 out of 5 average rating, 115 reviews

Seaside Serenity With Beautiful Aqua Vistas

Bright and clean condo with blazing fast wifi minutes from the beautiful, quiet island of Tierra Verde. Relax on our lanai with panoramic views of Boca Ciega, Gulf of Mexico & Tampa Bay & enjoy comforts of your own home. Watch exotic tropical birds, dolphins frolicking, & manatees right from the complex deck. Gateway to world renown Fort DeSoto Beach and 1 mile to St Pete Beach, we offer tennis courts, pool/hot tub, fitness room, docks, public grills, billiards table, & picnic tables.

Superhost

An aerial view captures a waterfront home surrounded by lush greenery and landscaped areas. The property features a dock along the private canal, with nearby residential homes in a peaceful neighborhood. Clear blue skies and calm waters complete the tranquil setting.

Home in Port Charlotte

4.89 out of 5 average rating, 9 reviews

#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.

Guest favorite

An outdoor deck features a wooden dining table and several benches, offering panoramic views of the water and surrounding mangroves. A charcoal grill is positioned nearby, with a large umbrella providing shade. The sky is bright with scattered clouds, enhancing the serene atmosphere.

Condo in St. Petersburg

4.89 out of 5 average rating, 118 reviews

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.

Superhost

Four images showcase various areas of the property. A game room with a pool table and ample natural light is featured. An outdoor putting green is surrounded by well-maintained landscaping. A screened-in patio with a pool is visible, along with a canal view lined by lush greenery.

Home in Ruskin

4.89 out of 5 average rating, 35 reviews

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!

Guest favorite

An aerial view captures a spacious property situated along a canal, showcasing a clear waterway lined with docks. Two boats are visible at the water's edge, with a well-maintained lawn and neighboring homes framed by palm trees, creating a serene waterfront setting.

Home in Port Charlotte

4.95 out of 5 average rating, 22 reviews

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.

Guest favorite

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

4.91 out of 5 average rating, 113 reviews

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.

Superhost

Apartment in Siesta Key

4.79 out of 5 average rating, 205 reviews

2/2 Beach House Apt on Siesta Key

Siesta Key Waterfront Apartment. Sleeps 6. Split plan 2 bedroom, 2 full bathroom “Beach House” w/ a full kitchen & recently updated! Bedroom 1: King. Bedroom 2: Queen. Living room: Sleeper sofa. 75” smart TV in the living room. A private screened lanai overlooking canal to Sarasota Bay. This is located in a super cute, quaint resort w/ other units. FREE KAYAKS & SUPs FOR GUESTS!

Top guest favorite

Aerial view of a serene canal, featuring a private dock adjacent to lush greenery. The calm water reflects the surrounding landscape, while a grassy area offers seating with views of the water. A covered boat slip is visible, enhancing the waterfront setting.

Cottage in Bradenton

4.96 out of 5 average rating, 106 reviews

Waterfront*3bd 2ba*Pool* PingPong Table*relaxing

• Fish from dock • Dog Friendly • 2 bd / 2 ba • Keyless Entry • Fire Table • Pool and pool floats • Putting Green • Selfie Wall **Add my listing to you wishlist by clicking the 🖤 in the upper-right corner* >> 10 miles to beach, *Award Winning Ana Maria Island >>7 miles to IMG Academy >> 11 miles to SRQ Airport >>2 miles from Pittsburg Pirates Training camp