Waterfront holiday rentals in Siesta Key

Find and book unique waterfront accommodation on Airbnb

Top-rated waterfront accommodation in Siesta Key

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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Top Guest favourite

Home in Sunset Beach

5 out of 5 average rating, 39 reviews

Luxury Waterfront Sunset Beach

Pure Luxury at Sunset Beach Live life to the like a Celebrity at this spectacular waterfront 3 story house all to yourself in Sunset Beach!! Fresh and Completely Renovated with impressive views of the water from every level! Your own private dock where you can pull up your own jet ski or boat! This location extremely unique with full Waterfront access & view from the house, and you can walk just steps away to the perfect white sands & warm ocean on Sunset Beach with the best of both worlds!

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 favourite

Home in Bradenton

5 out of 5 average rating, 42 reviews

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

Top Guest favourite

Home in Port Charlotte

5 out of 5 average rating, 13 reviews

Waterfront Escape on canal ocean access kayaks

This stylish waterfront home is perfect for group trips. This four bedroom two bath home has room for two families to fit comfortably. It has a variety of seating both indoor and outdoor to accommodate your stay. There is room to spend time together or find your own little quiet area. The home is located only minutes from the beach, pool, boat launch and fishing pier. Close to multiple waterfront restaurants and shopping. Only minutes from Sunseeker Resort, area boat tours and fishing charters

Superhost

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.

Top Guest favourite

Townhouse in Ruskin

4.93 out of 5 average rating, 107 reviews

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.

Guest favourite

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

Apartment in Treasure Island

4.82 out of 5 average rating, 141 reviews

2 PM check in-Boat dock-Pool-View-Walk to beach

Amazing Water views from the community New Dock Heated pool Charcoal Grills Bar and Restaurant within walking distance Pool chairs and umbrellas Fishing dock Full kitchen Boat dock (daily fee to dock boat) $35 a day fee for boat dock. The trailer cannot be stored on property Dog Policy- Under 25 lbs- No pit bulls or dobermans- Dogs must be on leash and not relieve themselves on the community grass. Must be walked outside the community and be house trained.

Guest favourite

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.

Top Guest favourite

Condo in St. Petersburg

4.97 out of 5 average rating, 119 reviews

Waterfront quiet condo w Pool by Madeira Beach

Incredible open water views from this 1 bedroom 1 bath QUIET CORNER UNIT on Boca Ciega Bay! Beautiful sunsets over water from your private 20ft balcony or from the heated pool and spa area with full views of Boca Ciega Bay. Private fishing pier on site. Exercise room overlooking pool. One of quitest units in building. Minutes to War Veterans’ Memorial Park, boat launch, boat rentals, trails, Madeira Beach, downtown St Pete

Guest favourite

Condo in St. Petersburg

4.86 out of 5 average rating, 291 reviews

Breathtaking Waterview & Pool View Condo

Waterfront condo with pool view. The view of the intercoastal is fantastic. Especially beautiful sunsets! Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking intercoastal or stay indoors and enjoy puzzles and games.

Top Guest favourite

Cottage in Bradenton

4.96 out of 5 average rating, 107 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