Waterfront vacation rentals near Siesta Beach

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Top-rated waterfront rentals near Siesta Beach

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

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Top guest favourite
A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.
Condo in Siesta Key
4.93 out of 5 average rating, 121 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door 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 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

Top guest favourite
A contemporary living area features a comfortable gray sofa with decorative pillows. A white coffee table sits centrally, while an accent chair with a colorful pattern offers additional seating. Two lamps illuminate the space, complementing the soft green walls.
Condo in Siesta Key
4.85 out of 5 average rating, 158 reviews

The Key to a Great Vacation!

Welcome to our one bedroom, one bath (4 piece) main floor condo. Recently renovated. Freshly painted with new furniture, a brand new king size memory foam mattress with contemporary decoration (with queen size pull out couch). Easily accessible with no steps to climb and close, convenient parking right outside the front door. Quiet, peaceful and near both Siesta Key Beach and the condo pool ensure a wonderful vacation. Walk across the street and enjoy one of the best beaches in the world.

Guest favourite
Bungalow in Siesta Key
5 out of 5 average rating, 19 reviews

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional queen sofa-bed allows accommodations for three guests.

Guest favourite
A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.
Condo in Longboat Key
4.9 out of 5 average rating, 195 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Top guest favourite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Condo in Siesta Key
4.97 out of 5 average rating, 347 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

Top guest favourite
A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.
Condo in Siesta Key
4.96 out of 5 average rating, 112 reviews

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Top guest favourite
Guest suite in Sarasota
4.9 out of 5 average rating, 347 reviews

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

Top guest favourite
A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.
Guesthouse in Bradenton Beach
4.99 out of 5 average rating, 194 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.

Top guest favourite
An aerial view captures a serene private pool encompassed by a stone patio, with several lounge chairs arranged nearby. Lush greenery and tropical plants border the scene, while a dark pond reflects the surrounding nature, enhancing a tranquil outdoor space.
Home in Bradenton
5 out of 5 average rating, 115 reviews

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Guest favourite
A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.
Home in Sarasota
4.93 out of 5 average rating, 106 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Charming 2BR/2BA Lakefront Home with Heated Pool – Just 2 Miles to Siesta Key Beach! Escape to this picturesque lakefront retreat, only 2 miles from the world-famous Siesta Key Beach. Perfect for families or groups, this spacious and beautifully furnished home offers a relaxing and memorable getaway. Lounge by the heated pool, soak in stunning lake views, or explore nearby attractions—this home is your ideal Sarasota vacation base.

Top guest favourite
Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.
Home in Bradenton Beach
4.96 out of 5 average rating, 111 reviews

Waterfront Retreat | Pool • Spa • Dock | Bridge St

🌴 Anna Maria Island Waterfront Oasis! Private dock + heated pool included. Relax by the pool, sip coffee on the dock, or walk just 5 minutes to the Gulf’s sugar-sand beach. Bright, updated home with stocked kitchen, fast Wi-Fi, smart TVs, and cozy beds—perfect for families or couples. Grill by the pool, dine outdoors, or fish from the dock. Boat/kayak friendly. Beach gear + parking included. Your peaceful island escape awaits.

Guest favourite
A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.
Condo in Siesta Key
4.92 out of 5 average rating, 116 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

Popular amenities for waterfront rentals near Siesta Beach

Quick stats about waterfront rentals near Siesta Beach

  • Total vacation rentals

    Explore 360 vacation rentals in Siesta Beach

  • Nightly prices starting at

    Siesta Beach vacation rentals start at $113 CAD per night before taxes and fees

  • Verified guest reviews

    Over 11,930 verified reviews to help you choose

  • Family-friendly vacation rentals

    290 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    330 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wifi availability

    360 of Siesta Beach vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Siesta Beach rentals

  • 4.8 Average rating

    Siesta Beach stays are highly rated by guests—averaging 4.8 out of 5!