Waterfront holiday rentals in Siesta Key

Apartment in Bradenton Beach

A large window reveals a stunning view of the sunset over the Gulf. Two red adirondack chairs are positioned to face the ocean, inviting relaxation. The soft glow of the setting sun reflects on the water, creating a serene atmosphere in the living space.

4.92 out of 5 average rating, 206 reviews

Beachfront Anna Maria Island w hot tub & Gulf view

You only have to go down 14 stairs from your second-floor beachfront condo to have your toes in the powder soft sand. A queen size bed with a soft mattress in the bedroom and a queen size pullout couch in the living room. Full kitchen in the unit and laundry available downstairs. Cable and high-speed internet included. One assigned parking spot. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach

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.

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!

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.

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.

Apartment in Longboat Key

4.99 out of 5 average rating, 167 reviews

Vitamin Sea Escape!

This charming seaside condo is 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort! To see all four of our listings, click on my Host photo and scroll down...!

4.94 out of 5 average rating, 124 reviews

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

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!

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.

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.

Apartment in Longboat Key

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.

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.

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.

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.

4.86 out of 5 average rating, 177 reviews

A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.

Cottage in Siesta Key

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

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.

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.

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 148 reviews

Sea Shell Ocean View On Beach Walk Everywhere Pool

Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 325+ reviews that ave FIVE STAR!

5 out of 5 average rating, 121 reviews

An aerial view captures a heated saltwater pool accompanied by a spa hot tub, surrounded by a stone patio and tropical landscaping. Loungers and Adirondack chairs are positioned for relaxation under a shaded umbrella. A serene pond and lush greenery create a tranquil backdrop.

Home in Bradenton

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!

Popular amenities for waterfront rentals in Siesta Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.85 out of 5 average rating, 34 reviews

The living area features a white sofa paired with two pink accent chairs, creating a refreshing ambiance. A wooden coffee table sits on a light-colored rug, while plants and beach-themed artwork add charm. Large sliding doors provide natural light and connect to the outdoor space.

Flat in Siesta Key

Condo Kokomo - stay ON the beach in Siesta Key!

4.98 out of 5 average rating, 127 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Flat in Bradenton

Sweet Retreat at Shorewalk!

Superhost

A beachfront property is showcased against a backdrop of the Gulf of Mexico. Lush palm trees and vibrant landscaping surround a paved driveway, while the clear blue water glistens in the distance under a bright sky. The home's roof reflects sunlight, enhancing the coastal ambiance.

Flat in Longboat Key

4.76 out of 5 average rating, 21 reviews

Private Beach, Outside Patio with Full Gulf View

4.84 out of 5 average rating, 277 reviews

A bright blue entrance door labeled 'Poolside Suite' is visible, leading into the suite. The door is framed by a light blue exterior, with a view of the pool area and palm trees in the background. Sunlight casts gentle shadows on the patio.

Flat in Siesta Key

Siesta Key - Poolside Suite - Studio - Free kayaks

4.96 out of 5 average rating, 114 reviews

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

Flat in Longboat Key

Longboat Key-OCEAN FRONT- on the beach

Superhost

A modern living room is presented with light gray walls and a large sliding glass door leading to a screened balcony. A comfortable sectional sofa sits against one wall, complemented by a decorative coffee table and a television displaying a serene beach scene.

Flat in Sarasota

4.82 out of 5 average rating, 92 reviews

Stylish Gray 2nd-Floor Condo w/ Heated Pool | 1BR

5 out of 5 average rating, 14 reviews

The exterior of the condo is shown, featuring a spacious deck surrounded by palm trees, with an umbrella providing shade. Large windows offer a view into the interior space, and ample outdoor seating is visible. A concrete path leads through the outdoor area.

Flat in Sarasota

Cozy Condo in Siesta key with boat dock

4.97 out of 5 average rating, 430 reviews

A serene view of the Manatee River showcases calm waters reflecting the sky. Lush greenery surrounds the area, accompanied by a covered dock nearby. An American flag flutters gently, and a hint of a charming structure with a porch is visible to the right.

Flat in Ellenton

Serenity on the Manatee

Waterfront house rentals

5 out of 5 average rating, 100 reviews

An inviting outdoor lanai is shown, featuring comfortable seating with colorful cushions. A wooden coffee table holds glassware, while a heated pool glistens in the background, surrounded by lush greenery. The screened area offers a seamless connection to the tranquil outdoor environment.

Home in Bradenton

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

4.94 out of 5 average rating, 110 reviews

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

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

4.94 out of 5 average rating, 103 reviews

The exterior of a charming two-story beach house features a vibrant color scheme with light blue and white accents. Adjoining palm trees provide shade, while a spacious porch with outdoor seating offers a welcoming view of the surrounding yard. A sandy area leads to the driveway.

Home in Anna Maria

2nd House from the Beach with No Roads to Cross

5 out of 5 average rating, 154 reviews

Home in Siesta Key

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

4.99 out of 5 average rating, 125 reviews

A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.

Home in Cove

Tranquility on the bay.

4.86 out of 5 average rating, 115 reviews

Home in Sarasota

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

4.94 out of 5 average rating, 106 reviews

A screened lanai encloses a private saltwater pool, featuring a shallow entry and a vibrant pink float. Two lounge chairs are positioned nearby, surrounded by greenery that enhances the serene pool area.

Home in Sarasota

Minutes to Siesta Key, heated pool & tiki on water

4.9 out of 5 average rating, 152 reviews

A serene beach scene is captured with gentle waves lapping against the shore. The clear water displays various shades of blue and green, while a sandy coastline extends into the distance. People can be seen enjoying the beach, with a bright blue sky overhead.

Home in Siesta Key

Sea Club II Garden House

Waterfront apartment rentals

A bright living area features large floor-to-ceiling windows that allow natural light to fill the space. A light-colored sectional sofa and a modern coffee table are present, along with a floor lamp. A balcony is visible in the background, showcasing views of greenery.

4.88 out of 5 average rating, 59 reviews

Beach Haven on Siesta Key Beach

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

4.86 out of 5 average rating, 188 reviews

Best Siesta Key Condo - Rarely available

Superhost

A spacious living area features a mix of comfortable seating, including a purple sofa and a black armchair. Large glass doors provide a view of the outdoor space and the surrounding landscape. A dining area is visible with a table set for four, accented by floral decor.

4.89 out of 5 average rating, 53 reviews

Dreamview • 1BR - Siesta Key Beach Sunset View

A detailed map highlights the location of Siesta Key, showcasing nearby points of interest and roadways. The Gulf of Mexico is indicated to the southwest, while the surrounding areas and other keys are marked, providing context for travel and exploration.

4.87 out of 5 average rating, 107 reviews

Bayside Sunrise Cottage on Siesta Key!

4.97 out of 5 average rating, 126 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Apartment in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

Apartment in Longboat Key

4.88 out of 5 average rating, 125 reviews

Sunset and beach view from your balcony Unit 403

A heated pool is surrounded by lounge chairs set on a white deck, with palm trees and lush greenery nearby. A multi-story building looms in the background, along with a tennis court visible at the side. A safety sign is placed by the gated entry.

4.89 out of 5 average rating, 109 reviews

Siesta Key Beach (OHAB) Townhouse #1 beach