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Waterfront holiday 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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Guest favourite
Bungalow in Siesta Key
4.92 out of 5 average rating, 24 reviews

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

The Siesta Key Bungalows offer a heated pool, courtyard & a dock on Heron Lagoon. This is a resort that has something for everyone. The Catamaran Bungalow features a bright and airy one bedroom space; with a large 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. The living room has a sofa that turns into a queen size bed, allowing for a max occupancy of three.

Guest favourite
A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.
Apartment in Siesta Key
4.9 out of 5 average rating, 134 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

Top guest favourite
Flat in Siesta Key
5 out of 5 average rating, 14 reviews

Siesta Beachfront Suite

Beach front, Beach view, private beach access makes Siesta Beach Front Suite your island visit a memory of a lifetime! Enjoy a beachfront home with direct beach access, this location will wow you! Nestled in a 7 unit private beach front location you will enjoy the very private beach experience few can imagine. This ground floor unit gives you beach access, beach views, plus your an easy 3 block walk to Siesta Village. Park at your front door walk to the #1 Beach in America out your back door!

Top guest favourite
A bright dining area features a white countertop with four woven bar stools. The open layout reveals a living space beyond, with large glass doors leading to a balcony. A welcome sign and a basket of snacks are positioned on the counter.
Apartment in Sarasota
5 out of 5 average rating, 25 reviews

Siesta Key Beach Retreat-Heated Pool-Water View

Our Siesta Key condo is the ideal retreat for families seeking both relaxation & adventure. Situated just a short walk from the famous beaches.Ideally located on the Intracoastal Waterway, you can enjoy water views from the great room, lanai, and primary bedroom when you're not enjoying the sandy shores right across the street. After a day at the beach, unwind by the pool or take the elevator to your top-floor condo, where you can enjoy the sunset over the water from the private screened lanai

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.
Apartment in Siesta Key
4.94 out of 5 average rating, 127 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 dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.
Apartment in Longboat Key
4.98 out of 5 average rating, 222 reviews

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Top guest favourite
The enclosed Lanai features large bay windows showcasing views of the Gulf of Mexico. A seating area includes wicker chairs and a coffee table. Light-colored walls are contrasted by wooden accents and a ceiling fan, creating a bright and airy atmosphere.
Flat in Siesta Key
4.94 out of 5 average rating, 124 reviews

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

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.
Apartment in Siesta Key
4.97 out of 5 average rating, 360 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. If we are booked check out our additional units under our profile.

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.
Apartment in Longboat Key
4.9 out of 5 average rating, 206 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 tranquil pool area is surrounded by palm trees, reflecting the clear blue sky. Lounge chairs are positioned around the pool's edge, inviting relaxation. The sun casts a warm glow over the scene, enhancing the peaceful ambiance of the resort.
Apartment in Siesta Key
4.98 out of 5 average rating, 125 reviews

Siesta Key For Me @ The Palm Bay Club

🏖️ Newly Renovated Siesta Key Condo | Ocean + Bay Views | Sleeps 6 📍 Bayside Suite at The Palm Bay Club | Walk to Beach ✨ ALL-NEW RENOVATIONS MAY 2025! Brand new bathrooms, flooring, doors, trim, granite countertops & more—be among the first to enjoy our stylish upgrade! Welcome to Condo #310 at The Palm Bay Club—a 2BR/2BA bright and breezy bayside condo with water views, modern upgrades, and private beach access just a short walk away. Sleeps up to 6 guests comfortably.

Guest favourite
A serene beach scene is depicted, featuring soft, white sand and gentle waves lapping at the shore. The horizon reveals a clear blue sky, with a few distant silhouettes of parasailers enjoying the view above the tranquil waters.
Apartment in Siesta Key
4.85 out of 5 average rating, 103 reviews

Newly renovated condo steps from SK private beach

Siesta Beach House are “Old Florida” style condos featuring a gated entrance to our private beach on the world famous Siesta Key Beach! Experience fun in the sun and on the beach like never before at this newly renovated two-story townhome style condo located just a few hundred feet from the private access beach with beach chairs and lounge chairs provided. In addition to having access to a great beach, guests will also have access to a temperature controlled pool.

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.
Apartment in Siesta Key
4.97 out of 5 average rating, 117 reviews

Palm Bay Club! Resort 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.

Popular amenities for waterfront rentals near Siesta Beach

Quick stats about waterfront rentals near Siesta Beach

  • Total holiday rentals

    Explore 380 holiday rentals in Siesta Beach

  • Nightly prices starting at

    Siesta Beach holiday rentals start at $114 SGD per night before taxes and fees

  • Verified guest reviews

    Over 12,470 verified reviews to help you choose

  • Family-friendly holiday rentals

    310 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    350 properties feature pools

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wifi availability

    380 of Siesta Beach holiday 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!