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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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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

Home in Bradenton

4.94 out of 5 average rating, 171 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).

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.

Cottage in Bradenton

4.93 out of 5 average rating, 329 reviews

Private King Bed Suite-Near AMI Beach-Walk D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 7:30AM. Please respect others. Walk to many great restaurants!

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 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.

Condo in Bradenton

4.97 out of 5 average rating, 126 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.

Condo in Sarasota

4.84 out of 5 average rating, 160 reviews

Best Gulf Coast Cond on Siesta - Christmas Special

Rarely Available for Christmas! Beautiful, open floor plan is the perfect location vacation. Condo is stocked with everything you will need to enjoy your stay. The resort is quiet and peaceful with direct access to the most beautiful private white sand beach. Also enjoy the Intra Coastal waterway with fishing and boat dock right on the property in our backyard next to the huge pool and bbq. This is the best of both worlds!!! Individually managed by owners.

Guesthouse in Bradenton Beach

5 out of 5 average rating, 148 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Condo in Bradenton

4.98 out of 5 average rating, 162 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.

Home in Siesta Key

4.96 out of 5 average rating, 101 reviews

Beachfront home with private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.

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.

Rental unit in Siesta Key

4.79 out of 5 average rating, 190 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!

Vacation rentals for every style

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Intimate homes. inviting architecture

Popular amenities for Siesta Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Rental unit in Bradenton Beach

4.89 out of 5 average rating, 121 reviews

Beachfront Studio right on the beach, Free Parking

Rental unit in Bradenton

4.97 out of 5 average rating, 78 reviews

Sweet Retreat at Shorewalk!

Rental unit in Bradenton Beach

4.88 out of 5 average rating, 213 reviews

Las Palmas Beach Rentals Unit 1

Rental unit in Longboat Key

4.95 out of 5 average rating, 93 reviews

Longboat Key-OCEAN FRONT- on the beach

Rental unit in Bradenton

4.86 out of 5 average rating, 51 reviews

Beach Oasis W/ Private Balcony 6 mi to Anna Maria

Rental unit in Sarasota

4.97 out of 5 average rating, 37 reviews

Stylish gray condo 6 min from Siesta+ heated pool

Rental unit in Anna Maria

4.83 out of 5 average rating, 64 reviews

Paradise on the beach! Upper level.

Rental unit in Bradenton

4.78 out of 5 average rating, 50 reviews

Modern Lakefront Condo. By IMG~Beaches~Restaurants

Waterfront house rentals

Home in Sarasota

4.81 out of 5 average rating, 43 reviews

Sarasota Waterfront Paradise Location, Location

Home in Siesta Key

5 out of 5 average rating, 137 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

Home in Sarasota

4.93 out of 5 average rating, 120 reviews

Lake Front House with a Pool

Home in Bradenton

4.89 out of 5 average rating, 131 reviews

Beautiful Lake View Home - Close Beaches / IMG

Home in Anna Maria

4.94 out of 5 average rating, 167 reviews

New Construction & Ready for Post-Hurricane Visits

Home in Siesta Key

4.91 out of 5 average rating, 138 reviews

Sea Club II Garden House

Home in Port Charlotte

4.94 out of 5 average rating, 50 reviews

Beautiful 3 bdrm home on a canal with heated pool.

Home in Venice

4.94 out of 5 average rating, 124 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

Waterfront condo rentals

Condo in Siesta Key

4.91 out of 5 average rating, 218 reviews

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky

Condo in Siesta Key

4.97 out of 5 average rating, 114 reviews

Siesta Key For Me @ The Palm Bay Club

Condo in Siesta Key

4.96 out of 5 average rating, 296 reviews

WE ARE OPEN—On the Beach; Siesta Key SunBum Studio

Condo in Sarasota

4.78 out of 5 average rating, 45 reviews

Beautiful Condo - Waterfront & Steps to Beach!

Condo in Bradenton Beach

4.99 out of 5 average rating, 114 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

Condo in Bradenton Beach

4.86 out of 5 average rating, 103 reviews

Oceanfront Condo for Beach Lovers

Condo in Indian Beach-Sapphire Shores

4.97 out of 5 average rating, 36 reviews

Sarasota Sunset Bay View Condo

Condo in Longboat Key

4.98 out of 5 average rating, 170 reviews

Cozy Condo by the Water!

Quick stats about waterfront rentals in Siesta Key

Total rentals
330 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
9.8K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
270 properties have a pool

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