Family-Friendly rentals near Crescent Beach

A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.

4.94 out of 5 average rating, 155 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

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, 61 reviews

Siesta Dunes 1st Floor Beach Front Retreat

🌞 Summer Special Enjoy an extra touch of convenience during your stay: complimentary beach umbrella setup each morning. Steps from the beach, this spacious 2 bedroom condo has everything you will need for your Siesta Key vacation. Located in the beautiful gated community of Siesta Dunes, with heated salt water pool, and its own private beach access, complete with beach chairs, umbrellas and towels. Stroll though the well-manicured grounds on your way to the pool, the sundeck and 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.

4.88 out of 5 average rating, 145 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!

4.99 out of 5 average rating, 112 reviews

An open living area features tiled flooring and soft lighting, with comfortable seating arrangements including a sofa and armchairs. A dining area is visible, showcasing a wooden table with chairs. Decorative touches such as artwork and a side cabinet enhance the space's charm.

Cottage in Sarasota

Quaint Cottage,150 steps away from Crescent Beach!

Nestled on the serene Crescent Street, this classic 1969 cottage, is just a short walk to the ground quartz sands of Siesta Key. The 500 sq foot private brick paver and stone backyard off the screened in lanai is fully fenced with custom built stainless outdoor kitchen, featuring a large grill, refrigerator, custom built stone bar with seating for 8 . Nearby is a blue glass gas fire pit with a seating area, over sized (9 ft. diameter) in ground "spool", loungers and a large circular daybed.

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.86 out of 5 average rating, 108 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.

4.99 out of 5 average rating, 105 reviews

Private Standalone Home - Walk to Siesta Key Beach

Welcome to your private escape on Siesta Key, an ideal retreat for a relaxing vacation. This renovated, standalone single-level home is tucked away on a quiet, tree-lined street, offering rare privacy just a short walk from Siesta Key’s famous white-sand beaches, restaurants, and bars. Surrounded by lush tropical gardens, enjoy peaceful seclusion plus access to a large heated community pool and an intracoastal pier, perfect for morning coffee, afternoon fishing, or sunset tropical drinks.

4.95 out of 5 average rating, 155 reviews

A bright and airy living space features a modern sofa facing a sleek coffee table. The open kitchen is visible in the background, showcasing white cabinetry and bar seating with stylish stools. Light fills the room through large windows, enhancing the spacious feel.

Condo in Sarasota

Your Modern Beachside Getaway!

Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

A beachfront pool area is shown under a bright sky, featuring palm trees and umbrellas around the pool. Guests are seen enjoying the water, with lounge chairs and colorful towels placed around the poolside. The ocean is visible in the background, completing the serene atmosphere.

4.86 out of 5 average rating, 153 reviews

Private Beach Siesta Key Resort Jamaica Royale

Jamaica Royale is a Beach Front Oasis, offering a private community with our own beach access and 3 heated pools . Enjoy our sidewalks, directly to the beach with no roads to cross; only residents are allowed onto the property, offering a family-safe paradise! Put your toes in the white sands of Siesta Key, where we have a private beach pavilion and lounge chairs! Look at our overview, to see our excellent location! We are in the first set of villas, closest to the beach.

A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.

4.97 out of 5 average rating, 130 reviews

Private Beach with Loungers · 2 Pools & Bay View

Beachside resort life for families, groups and remote workers seeking easy beach access and active days. This oversized & Fully Renovated 2‑bed, 2‑bath condo sits in a gulf-to-bay complex so you can walk to the famed Siesta Key sand and hop the island trolley outside your door. Enjoy bay views, unwind in heated pools and the hot tub, use the on-site gym and courts, and take advantage of provided beach chairs, umbrella and wagon for effortless beach days.

4.93 out of 5 average rating, 161 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. (Daytime weekday construction nearby may cause intermittent noise.)

A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.

4.88 out of 5 average rating, 173 reviews

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

A spacious and quiet 2-floor, 2 bedroom, 2.5 bathroom condo that lives like home and is close to everything Siesta Key offers. Spread out and enjoy YOUR vacation! Your condo features large rooms, comfy and modern surroundings, (2) Master Bedrooms upstairs, and you are steps away from a gorgeous heated pool that you can view from your lanai. This is the perfect condo for you and your family to relax in and simply enjoy your time in Siesta Key!

4.98 out of 5 average rating, 122 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

Popular amenities for family-friendly rentals near Crescent Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 161 reviews

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

A landscaped pathway is flanked by vibrant flowering plants and palm trees. Neatly trimmed grass lines the walkway, leading to a serene courtyard. Soft lighting from a garden lantern adds to the peaceful ambiance of this tropical setting.

4.94 out of 5 average rating, 170 reviews

Siesta Key Serenity At The Palm Bay Club

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, 136 reviews

Siesta Key For Me @ The Palm Bay Club

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, 388 reviews

On the Beach; Siesta Key SunBum Studio

5 out of 5 average rating, 113 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.

4.91 out of 5 average rating, 151 reviews

St Armand's Mid-Century Oasis

4.82 out of 5 average rating, 106 reviews

Condo in Sarasota

LJ's Cottage 2

5 out of 5 average rating, 13 reviews

Siesta Key House, Pool & Hot Tub, 1 mile to beach

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 116 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

5 out of 5 average rating, 14 reviews

Apartment in Siesta Key

Bougie Beach Bungalow – Siesta Key, Florida

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, 32 reviews

Penthouse Beautiful Ocean Views

5 out of 5 average rating, 8 reviews

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

A modern living area features a comfortable sectional sofa, accented by textured cushions. A flat-screen TV is mounted on the wall above a wood panel, while large sliding doors invite natural light and provide access to the patio. Indoor plants add a touch of greenery.

4.85 out of 5 average rating, 149 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

4.97 out of 5 average rating, 38 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

5 out of 5 average rating, 9 reviews

Silent G Siesta Key Private Bungalow by the Beach

Vacation home in Siesta Key

A vibrant sunset is captured over Siesta Key Beach, with palm trees silhouetted against the colorful sky. The horizon features a gradient of warm hues, creating a tranquil ambiance. Nearby structures are visible beneath the palms, offering a sense of proximity to the sandy shoreline.

4.98 out of 5 average rating, 130 reviews

Siesta Beach View : Pineapple Bungalow Efficiency

Family-friendly home rentals with a pool

5 out of 5 average rating, 7 reviews

Siesta Key Villa | Pool + Free Daily Activities

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!

5 out of 5 average rating, 3 reviews

Siesta Key*GULF SIDE oasis*PRIVATE BEACH*Pool

An aerial view captures the beachfront property nestled among greenery, with sandy pathways leading to the beach. The top floor condo is highlighted, surrounded by other buildings, while the striking blue Gulf waters stretch in the background, meeting the clear sky.

5 out of 5 average rating, 46 reviews

Beachfront 180-Degree View, Walk to Village!

4.83 out of 5 average rating, 6 reviews

Beach Access, Clean, Updated, Heated Pool & MORE

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.

5 out of 5 average rating, 36 reviews

New Villa on Siesta Key! Pool & Walkable to Beach

4.96 out of 5 average rating, 26 reviews

Villa in Siesta Key

Intracoastal Escape Walk to Beach & Dining

A sunset view shows the calm ocean meeting the horizon, with soft orange and pink skies. The coastal area is framed by several low-rise buildings and lush palm trees, creating a serene atmosphere. Traffic lights and roads are visible in the foreground, leading toward the beach access.

4.94 out of 5 average rating, 17 reviews

Anchorage Resort 2 Bdrm Condo 9th Flr, Pool, Beach

Family-friendly home rentals with Wifi

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, 72 reviews

2 BR condo in Siesta Key w/ Private beach access

An outdoor patio area features a glass dining table surrounded by six metal chairs. Lush palm trees and tropical plants provide a vibrant backdrop to the swimming pool, which is framed by a sunlit brick deck.

4.97 out of 5 average rating, 58 reviews

NO Bunks- King beds, Garage, Private Beach

5 out of 5 average rating, 10 reviews

A villa with a light-colored exterior features a spacious driveway made of pavers. Lush tropical landscaping adds color, while a large parking garage is visible on the right side. In the background, a multi-story building is partly shown under a partly cloudy sky.

Villa in Sarasota

Newly Remodeled Luxury Beach Villa on Siesta Key!

4.9 out of 5 average rating, 20 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.

Condo in Sarasota

Condo on Siesta Beach with a view!

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, 97 reviews

Breathtaking Beachfront Views in Siesta Key

4.92 out of 5 average rating, 13 reviews

Apartment in Sarasota

Parrots beach bungalow

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.

4.94 out of 5 average rating, 77 reviews

Beach & Pool Open! Direct Beachfront Condo! Sunset

An inviting living area features a comfortable grey sofa and two armchairs surrounding a wooden coffee table. A flat-screen television is mounted on the wall, while a light rug with subtle stripes enhances the open layout leading to a modern kitchen area.