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, 111 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.

Superhost

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

4.93 out of 5 average rating, 169 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, 249 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

Condo in Ruskin

4.91 out of 5 average rating, 124 reviews

Beach Condo with water view!

Bright, updated, sunrise and canal view unit located in the fabulous Resort Community of Little Harbor. This unit is perfectly placed and close to everything you need. Unit features 2 queen beds, a full size handicap accessible bathroom w/walk in shower with spa jets and handrails. Free wifi, large screen HDTV, and while there are no kitchen facilities; there is a mini fridge, coffee maker, microwave and airfryer/toaster. Unit is next to restaurants, pools and tiki bar (live music daily)

Guest favorite

Rental unit in Ruskin

4.87 out of 5 average rating, 119 reviews

Sunset Del Mar (studio with a view)

Living the Florida lifestyle right on beautiful Tampa Bay. The Inn at Little Harbor is a secluded resort style community offering waterfront accomodations with amenities that include 2 heated pools, jacuzzi, tennis courts, a beautiful sandy beach, 2 full service restaurants/bars with live music,kayak and paddle board rentals, jet ski rentals, boat rentals and fishing charters and some of the most beautiful sunsets you have ever seen. Amenities are within walking distance from your doorstep.

Superhost

Townhouse in Ruskin

4.93 out of 5 average rating, 213 reviews

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

Guest favorite

Condo in Bradenton

4.97 out of 5 average rating, 122 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, 161 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 Bradenton

4.99 out of 5 average rating, 144 reviews

My Peaceful place on the bay.

Tucked away from the hustle and bustle, my mobile home is located in a very unique neighborhood right on the bay with a little beach 2 min. down the road from my house, where you can sit and enjoy the views or fish. The homes are a combination of mobile homes like mine and houses with the most wonderful people of all walks of life. Very quiet, friendly and 5 min. to Bradenton beach and 10 min. to AMI.

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!