Waterfront vacation rentals in Siesta Key

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Top-rated waterfront accommodations in Siesta Key

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

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Guest favourite

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 favourite

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 favourite

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, 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 favourite

Condo in Treasure Island

4.95 out of 5 average rating, 148 reviews

Exquisite, Modern Waterfront Condo, A Hidden Gem!

Sip coffee in the seating area, read a book by the pool, or enjoy a drink on the beach! Beautifully renovated, second-floor waterfront condo in Treasure Island, 2 blocks from the beach. A short walk to restaurants & shopping includes everything you need to enjoy your vacation. The condo offers high-speed internet, a full kitchen with all cooking needs, 65" Wi-Fi TV, Netflix, a community grill/pool washer/dryer, and free parking steps away. Close to Downtown St Petersburg, Clearwater & Tampa.

Guest favourite

Condo in Ruskin

4.92 out of 5 average rating, 123 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 favourite

Rental unit in Ruskin

4.86 out of 5 average rating, 118 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.

Guest favourite

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.

Superhost

Rental unit 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

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.

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 favourite

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.