Waterfront holiday rentals near Crescent Beach

4.79 out of 5 average rating, 184 reviews

Home in Siesta key

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Welcome to our 3 Bedroom 2 Bathroom Siesta Key Beach House. Full kitchen. Walk to beach. We provide chairs & towels for the Beach Walk to Beach access #12 on Siesta key Lots of places to eat and drink, close by. Free WIFI Daily, Weekly rentals. Swimming Pool on site King Bed in Master bedroom, Bedroom 2 and 3 both have Queens This home is in a great location and it is only a short walk to shops , restaurants and Beach. This home has 2 x 1 bedroomed units attached and is great for families

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.

4.89 out of 5 average rating, 139 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!

4.86 out of 5 average rating, 111 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.

4.79 out of 5 average rating, 103 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

Apartment in Longboat Key

A clear view of the tranquil waters reveals a vibrant blue float anchored in the shallows. The backdrop features a picturesque beachside resort with palm trees, framed by a clear blue sky and soft sandy shorelines.

4.98 out of 5 average rating, 232 reviews

Island Time: Open Sun, $199/nt + Fees!

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...!

4.93 out of 5 average rating, 138 reviews

Siesta Key condo, beach access, heated pool

This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki bar, or try your luck fishing on the pier, all while viewing the boats on the intercoastal! Included is private deeded beach access that is just a easy 5 min walk. Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. 65" tv free wifi Netflix Disney+. Boat slip available up to 24'

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.

4.83 out of 5 average rating, 138 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Our newly renovated condo is located on Siesta Key's award winning Crescent Beach. Our unit is has all of the amenities of home for your convenience. The primary bedroom has a king sized bed and its own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

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, 372 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.

4.87 out of 5 average rating, 291 reviews

An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.

Cottage in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

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, 194 reviews

Private Beach & Intracoastal Waterfront

Experience the best of Florida’s Gulf Coast in this bright, spacious condo with an open floor plan and everything you need for a relaxing stay. Enjoy the rare best of both worlds location with direct access to a private white-sand Gulf beach and Intracoastal waterfront views right behind the property. Amenities include a heated pool, BBQ area, fishing dock, and boat dock. Quiet, peaceful resort. Owner-managed; monthly stays include a complimentary second cleaning. 🌴

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, 118 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.

4.92 out of 5 average rating, 153 reviews

Gulf Views | Walkable | Spacious

Spacious Gulf-view 2BR condo perfect for families & groups—featuring a rare 2-queen guest room, king master, and plenty of room to spread out. Walk to the beach, restaurants, coffee, and more—no car needed. Easy beach access + FREE loungers make beach days effortless. Heated pool, fast WiFi & fully stocked with beach gear. Clean, spacious & comfortable in a prime, walkable location.

Popular amenities for waterfront rentals near Crescent Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.91 out of 5 average rating, 139 reviews

Flat in Bradenton Beach

Newly Remodeled Beachfront Studio - On the sand!

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, 135 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!

4.88 out of 5 average rating, 231 reviews

A dining table showcases a glass top with intricately woven placemats. Each setting features decorative plates and neatly folded napkins secured with decorative rings. Sheer curtains frame the window, offering glimpses of lush palm trees outside.

Flat in Bradenton Beach

Las Palmas Beach Rentals Unit 1

4.97 out of 5 average rating, 58 reviews

A spacious living area is depicted with modern furnishings, including deep blue sofas and a light wooden coffee table. A large TV is mounted on a neutral-colored wall. A dining space with four chairs is visible in the background, along with decorative plants enhancing the ambiance.

Flat in Siesta Key

Across from #1 Siesta Beach & walk to town

4.96 out of 5 average rating, 119 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

4.93 out of 5 average rating, 29 reviews

A spacious wrap-around patio is showcased with tiled flooring, offering unobstructed views of the water and sky at sunset. A dining table and chairs are positioned for outdoor relaxation, framed by palm trees, while sliding glass doors lead into the interior space.

Flat in Siesta Key

Wave Whisper in Siesta Key

5 out of 5 average rating, 21 reviews

Flat in Longboat Key

New Modern Longboat Key*5 Steps to Sand*Heatd Pool

Waterfront house rentals

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 112 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

A spacious outdoor living area is shown, featuring a seating arrangement with floral-patterned cushions and a wooden coffee table. A dining table, set for six, is positioned nearby. The screened lanai offers views of the pool, surrounded by greenery and clear blue skies.

5 out of 5 average rating, 103 reviews

NEW Saltwater Pool + Spa | Mins to AMI Beaches/IMG

A charming house with a well-manicured lawn is framed by lush greenery. The front porch is accented by decorative red doors, and a stone walkway leads up to the entrance. Large trees provide shade over the landscaped yard.

5 out of 5 average rating, 102 reviews

Peaceful Braden River Oasis: Main House

4.99 out of 5 average rating, 102 reviews

An aerial view of Siesta Key displays a coastal neighborhood with a network of waterways. The vibrant blue water contrasts with the greenery and residential homes, highlighting the island's tranquil setting. The city skyline of Sarasota is visible in the distance, framing the picturesque scene.

Home in Sarasota

Siesta Key Beach Getaway

A private heated pool is surrounded by lush palm trees and a well-maintained lawn. An outdoor dining area with a large umbrella is visible, along with two lounge chairs positioned near the pool. The area is brightened by clear blue skies and sunlight.

5 out of 5 average rating, 158 reviews

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

4.84 out of 5 average rating, 107 reviews

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!

A spacious rooftop terrace overlooks a marina filled with boats. Lounge chairs are arranged for relaxation, surrounded by greenery. Outdoor tables are set for dining, with views of water and distant shorelines under a partly cloudy sky.

4.98 out of 5 average rating, 126 reviews

Bradenton Gem | IMG & AMI | King Ste + Beach Gear

4.9 out of 5 average rating, 120 reviews

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

Waterfront apartment rentals

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, 31 reviews

Penthouse Expansive Ocean Views

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.

4.88 out of 5 average rating, 115 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, 56 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

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, 128 reviews

Siesta Key For Me @ The Palm Bay Club

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.

4.95 out of 5 average rating, 22 reviews

Siesta Key - Intracoastal, Pool & the Beach!

Apartment in Bradenton Beach

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

4.99 out of 5 average rating, 170 reviews

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

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

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.

4.85 out of 5 average rating, 114 reviews

Siesta Key Beach (OHAB) Townhouse #1 beach

Other waterfront holiday rentals

An open-concept living and dining area is highlighted, featuring a white dining table with six chairs, a comfortable seating arrangement, and large glass doors leading to a balcony. A neutral color palette is complemented by a decorative mirror and modern lighting.

4.97 out of 5 average rating, 66 reviews

2 BR condo in Siesta Key w/ Private beach access

4.91 out of 5 average rating, 11 reviews

Bungalow in Siesta Key

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

A comfortable living area is furnished with two light-colored leather sofas and a circular glass coffee table displaying decorative items. Soft lighting is provided by a floor lamp, and framed art is mounted on the walls, adding a touch of decor. The space opens to a kitchen area in the background.

4.96 out of 5 average rating, 78 reviews

Charming Siesta Key Condo Just Minutes from Beach

4.96 out of 5 average rating, 24 reviews

A stunning beach scene displays soft white sand contrasted by gentle blue waters under a clear sky. Palm trees are visible in the foreground, while sun loungers and colorful beach umbrellas dot the landscape, encouraging relaxation and enjoyment of the serene coastal environment.

Apartment in Sarasota

Siesta Key 2B2B Condo On Private Beach

5 out of 5 average rating, 7 reviews

Apartment in Sarasota

Johnnys Island Palm | Walk to Beach & Dining

Two refreshing cocktails are presented in clear glasses, one pink and one yellow, each garnished with a slice of pineapple. A vibrant pink flower and seashells sit on a textured mat, with a calm beach and turquoise waters in the background under a clear blue sky.

4.77 out of 5 average rating, 62 reviews

Luxury Waterfront Views/Pool/1400sf/2 min to Beach

4.83 out of 5 average rating, 12 reviews

Palm thatched umbrellas provide shade over teal lounge chairs arranged on a sandy beach. The shoreline is visible in the distance, with clear blue skies overhead and beach equipment scattered in the background, enhancing a relaxed beach atmosphere.

Apartment in Sarasota

Condo on Siesta Beach with a view!

A spacious family room is presented with a large sectional couch, accented by colorful pillows. A 60-inch smart TV is mounted on a blue accent wall, showcasing a tropical scene. The dining area is visible in the background, featuring a table with light-colored chairs under modern lighting.