Waterfront holiday rentals near Crescent Beach

4.92 out of 5 average rating, 24 reviews

Bungalow in Siesta Key

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.

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 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.

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

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.

4.88 out of 5 average rating, 104 reviews

A comfortable living area showcases a gray sofa with decorative cushions and a round coffee table at its center. Two accent chairs are positioned nearby. A dining table for four is visible, with large sliding glass doors providing natural light and views of the outdoor area.

Townhouse in Siesta Key

Siesta Key - Private Beach Access - 2BR Retreat

Stay, relax, and play-your Siesta Key retreat is here. Make lasting memories at this cozy Siesta Key townhouse, just steps from the famous white sands. Private beach access and no roads to cross, it’s safe and stress-free for the whole family. Relax in spacious living areas, cook in the full kitchen, or enjoy games and movie nights after a day in the sun. Highlights include 2 bedrooms, private parking, nearby shops and dining, and the free Siesta Key Breeze Trolley for easy island exploring.

4.98 out of 5 average rating, 222 reviews

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.

Condo in Longboat Key

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...!

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.

4.9 out of 5 average rating, 206 reviews

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

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!

Popular amenities for waterfront rentals near Crescent Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Apartment in Bradenton Beach

4.91 out of 5 average rating, 137 reviews

Newly Remodeled Beachfront Studio - On the sand!

4.91 out of 5 average rating, 90 reviews

A vibrant sunset is captured over the calm ocean waters, with the sun partially dipping below the horizon. A silhouette of a bird is seen flying across the sky, adding movement to the serene scene. The warm orange and yellow tones dominate the visual landscape.

Apartment in Siesta Key

Siesta Sunsets Suite

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.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

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.

Apartment in Siesta Key

Siesta Key - Poolside Suite - Studio - Free kayaks

Apartment in Longboat Key

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.

4.96 out of 5 average rating, 114 reviews

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.

Apartment in Sarasota

4.82 out of 5 average rating, 92 reviews

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

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.

Apartment in Ellenton

Serenity on the Manatee

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.

Apartment in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

Waterfront house rentals

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 Bradenton

Tranquility on the bay.

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.

4.94 out of 5 average rating, 106 reviews

Minutes to Siesta Key, heated pool & tiki on water

4.86 out of 5 average rating, 116 reviews

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

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

A serene outdoor seating area features several lounge chairs with cushions, positioned on a brick patio overlooking tranquil water. The setting is complemented by a soft sunset in the background, with lush greenery visible across the bay.

4.89 out of 5 average rating, 106 reviews

Oceanfront home w/sunset views of Sarasota Bay

4.96 out of 5 average rating, 23 reviews

Sarasota Serenity - Minutes to Beach

Waterfront condo accommodation

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!

Aerial view captures the pristine beach alongside the expansive manicured grounds of a gated community. The layout features several buildings with red roofs, centered around a heated salt water pool. The shoreline and beach-goers are visible in the distance.

4.98 out of 5 average rating, 52 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

An aerial view captures a picturesque community along the inter-coastal waterway, showcasing a cluster of condos with terra-cotta roofs. The lush greenery surrounds the buildings, and the serene blue waters reflect the sky, with the distant coastline visible beneath a sunny atmosphere.

4.83 out of 5 average rating, 53 reviews

Relaxing Siesta Key 3rd Floor Condo

A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.

4.82 out of 5 average rating, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

5 out of 5 average rating, 8 reviews

Spectacular 2B Condo on Siesta Key Beach

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.

Condo in Bradenton

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

A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.

5 out of 5 average rating, 75 reviews

Breathtaking Beachfront Views in Siesta Key

An expansive view showcases the Gulf waters and sandy beach from a fourth-floor corner unit. Lounge chairs are visible on the beach, while a balcony railing frames the scene. Bright skies are complemented by gentle waves rolling onto the shore.

4.93 out of 5 average rating, 75 reviews

Beach & Pool Open! Direct Beachfront Condo! Sunset

Other waterfront holiday rentals

4.98 out of 5 average rating, 95 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

A bright dining area features a glass-top table set with blue placemats and white plates. Floor-to-ceiling windows provide unobstructed views of the beach. Light-colored cabinetry and modern appliances are visible in the kitchen area, enhancing the overall spaciousness.

5 out of 5 average rating, 9 reviews

2BR Penthouse - Stunning Beach Views on Siesta Key

Superhost

Aerial view of the Siesta Key beachfront, highlighting the Crescent Arms condominium complex set against the powdery white sands and turquoise waters of the Gulf of Mexico. The surrounding area features other buildings and beachgoers enjoying the sun and surf.

4.76 out of 5 average rating, 25 reviews

Beachfront Condo - 2BR Luxury - Crescent Beach

A clear view of the ocean is presented, complemented by lush greenery in the foreground. Buildings line the coastline, and a blue sky with light clouds enhances the scene, creating an atmosphere of tranquility and connection to nature.

4.97 out of 5 average rating, 29 reviews

Penthouse Expansive Ocean Views

Apartment in Bradenton Beach

5 out of 5 average rating, 23 reviews

Beachfront Corner Condo | Sunset Gulf Views

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

4.91 out of 5 average rating, 34 reviews

Coastal Retreat near Siesta Key Beach and Downtown

A spacious living area features a large sectional sofa and a decorative wooden side table. Natural light floods through expansive glass doors, leading to an outdoor dining space. A soft area rug provides a cozy touch, while wooden shelves and a TV complete the inviting atmosphere.

4.95 out of 5 average rating, 38 reviews

Private Beach Access, Two pools, Excelsior

A spacious living area features comfortable wicker furniture and a neutral color palette. Large glass doors provide views of the greenery outside, while a subtle area rug adds texture to the tiled floor. A decorative painting is mounted on the wall, enhancing the coastal theme.