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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Guest favorite

Condo in Tierra Verde

4.72 out of 5 average rating, 110 reviews

Seaside Serenity With Beautiful Aqua Vistas

Bright and clean condo with blazing fast wifi minutes from the beach on a 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.

Guest favorite

Home in Longboat Key

4.86 out of 5 average rating, 110 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

Guest favorite

Home in Bradenton

4.94 out of 5 average rating, 165 reviews

Peaceful Braden River Oasis: Cottage

Come get away to this river retreat just outside of Lakewood Ranch. This property has three separate rental units on it including this charming single bedroom cottage with access to the river. It comes with everything you need to enjoy a wonderful vacation! The other units on this property are the Guest House, a larger studio unit 1 bed/1 bath sleeps 2 (Search Peaceful Braden River Oasis: Guest House) and the Main House, a 2 bed/2 bath sleeps 7 (search Peaceful Braden River Oasis: Main House).

Superhost

Guesthouse in Englewood

4.91 out of 5 average rating, 248 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Guest favorite

Home in Englewood

4.96 out of 5 average rating, 113 reviews

Charming & Comfy Waterfront Oasis ~ Views ~ Dock!

A 2 bedroom 2 bathroom* waterfront house on Forked Creek in Englewood, Florida 2.5 miles away from Manasota Key. This is a 1,100 sq. ft. single family home on a natural deep water creek with a boat dock. House comes fully furnished and fully equipped. King size and queen size beds in the 2 bedrooms. Full size sofa and IKEA recliners in the "Florida Room", desk area, high speed wireless internet and cable and Netflix ready TV, towels, beach chairs, grill, etc. Air mattress is provided.

Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 118 reviews

The Seabreeze Cottage with peaceful water views

Welcome to my newly renovated townhouse! The Seabreeze Cottage is a two bedroom, 1.5 bath, colorfully decorated townhouse with a fun beachy vibe! It has beautiful and peaceful water views of the lake. It’s within 30 minutes of the Gulf Coast’s best beaches, including Anna Maria Island, Longboat Key, and Siesta Key. Only ten miles from Sarasota airport (SRQ) and about one hour from Tampa airport (TPA). It’s just 7 miles or 15 min from the world renowned IMG Academy.

Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 159 reviews

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Guest favorite

Cottage in Ruskin

4.91 out of 5 average rating, 101 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.

Guest favorite

Home in Ruskin

4.92 out of 5 average rating, 222 reviews

Pura Vida - Tropical Getaway Overlooking Tampa Bay

Beautifully decorated and luxurious three bedroom, two bath with breathtaking views and direct access to Tampa Bay. The water can be seen from every room! The property is located on a corner lot with two bedrooms facing the canal and Patrick's Island while the master bedroom faces Tampa Bay. Fish, kayak, or just relax and take in nature. Frequent dolphin and manatee encounters are common! We love our home!

Superhost

Rental unit in Siesta Key

4.79 out of 5 average rating, 189 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!

Guest favorite

Rental unit in Bradenton Beach

4.87 out of 5 average rating, 125 reviews

Low Tide @ Tides Inn

Sunny and spacious bungalow with views of the Intra-Coastal Waterway. Bring your boat and fishing gear and fish off the new dock. Coastal Eco-Tours are available within minutes. Centrally located within minutes to the beach and Bridge Street. Newly remodeled mid-century bungalow that offers many close activities for all the family.

Guest favorite

Home in North Port

4.81 out of 5 average rating, 124 reviews

Panoramic waterfront with views and pool

Relax and enjoy the panoramic waterfront views of the Miakahatchi river waterway from our deck or inground pool off a Tip lot - Fish right off the dock. Beautiful furnished vacation home on a quiet cul de sac with fenced yard. Short drive to several local beaches. Parents please use caution with canal and pool.