Family-friendly rentals near Crescent Beach

A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.

5 out of 5 average rating, 164 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to Mi Casa Siesta on Siesta Key, the #1 beach in the country! Gorgeous newly renovated one-bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

4.8 out of 5 average rating, 195 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, 142 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!

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, 107 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, 102 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, 153 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.

Apartment 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 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, 128 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.)

4.92 out of 5 average rating, 162 reviews

Apartment in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

An open concept living area features a blend of modern and comfortable furnishings. A dark wooden coffee table is centered on a textured rug, with a stylish mirror and a ceiling fan overhead. Large glass doors allow natural light and views of the screened Florida Room.

4.91 out of 5 average rating, 101 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

Welcome to your slice of paradise! Our stunning vacation rental offers the ultimate beachside getaway, providing you with a luxurious and unforgettable experience right on the main strip of the world-renowned Siesta Key Beach and the vibrant Siesta Key Village. The apartment or best referred to as CasaPlaya, features open concept living, a chic kitchen, fully upgraded bathroom and screened in Florida Room for your enjoyment.

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, 163 reviews

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

Rad’s Cozy Cottage – Siesta Key Private Home. Enjoy a heated saltwater pool, canal-front dock, and putting green at this one-of-a-kind tropical getaway. Steps from Siesta Village (shops, restaurants, nightlife) and the powdery-white sands of Siesta Key Beach. Fully updated 2BR/1.5BA cottage with modern kitchen, AC, Wi-Fi, and washer/dryer. Sleeps 6 (king + 2 twins + sofa). Book your island paradise!

4.98 out of 5 average rating, 120 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, 160 reviews

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

4.96 out of 5 average rating, 207 reviews

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

Home in Bradenton beach

Sea AMI

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

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, 134 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, 386 reviews

On the Beach; Siesta Key SunBum Studio

5 out of 5 average rating, 111 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.

4.92 out of 5 average rating, 150 reviews

St Armand's Mid-Century Oasis

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

4.98 out of 5 average rating, 147 reviews

Cozy Boho Bungalow Pool/Spa Downtown Sarasota

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 116 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

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

4.97 out of 5 average rating, 106 reviews

A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.

Home in Holmes Beach

Salty Harbor AMI pool retreat near the Beach

5 out of 5 average rating, 6 reviews

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

4.93 out of 5 average rating, 44 reviews

Fish, Float & Heated Pool! Walk to Siesta Beach

4.97 out of 5 average rating, 37 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

Holiday 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

5 out of 5 average rating, 10 reviews

Flat in Siesta Key

Siesta Key Luxury Penthouse, walk to Beach&Village

Family-friendly home rentals with a pool

A refreshing cocktail is displayed on a wooden table, featuring vibrant garnishes of a cherry and a slice of lemon. The background showcases a serene beach scene, with soft white sand and calming turquoise waters under a clear blue sky.

4.91 out of 5 average rating, 118 reviews

#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf

5 out of 5 average rating, 8 reviews

Luxury 3B/3B waterfront home w/ pool + boat access

Aerial view captures the waterfront community and surrounding greenery, with buildings and resort-style residences aligned. The inter-coastal waterway reflects the sunlight, while the shoreline is lined with lush landscaping. The serene blue of the sea can be seen in the distance, enhancing the coastal ambiance.

4.71 out of 5 average rating, 59 reviews

Amazing Siesta Key Condo in Midnight Cove II

5 out of 5 average rating, 3 reviews

Siesta Key*GULF SIDE oasis*PRIVATE BEACH*Pool

5 out of 5 average rating, 4 reviews

Huge Villa! Sunroom, Pool, Near Crescent Beach!

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, 171 reviews

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

A bright living room features a large sectional sofa adorned with various cushions. A flat-screen TV is mounted on the wall, presenting a serene beach scene. Natural light enters through sliding glass doors, which lead to a balcony, while decorative wall baskets add visual interest.

4.85 out of 5 average rating, 26 reviews

2B/2BA Penthouse End-Unit Condo

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, 35 reviews

New Villa on Siesta Key! Pool & Walkable to Beach

Family-friendly home rentals with wifi

5 out of 5 average rating, 6 reviews

Casa Bella Vita | Walk to Crescent Beach!

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!

A comfortable living area features light blue leather sofas arranged around a glass coffee table. A large TV is positioned on a wooden stand, while sliding glass doors provide ample natural light and a view of the outdoors.

4.67 out of 5 average rating, 24 reviews

Anchorage Resort 2 Bdrm Condo 6th Flr, Pool, Beach

5 out of 5 average rating, 4 reviews

A spacious living area is featured with large windows that allow natural light to fill the room. Comfortable seating includes a sectional sofa, two chairs, and a round coffee table. An expansive flat-screen TV is positioned on the floor, providing entertainment options.

Apartment in Sarasota

North Water View - Residence 310

A spacious kitchen area features sleek cabinetry and a large center island with a striking stone surface. Wooden beams add a rustic touch overhead, while modern appliances are seamlessly integrated. Natural light floods the space, creating an inviting environment for meal preparation and gathering.

5 out of 5 average rating, 4 reviews

Rustic Sands - 650

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, 94 reviews

Breathtaking Beachfront Views in Siesta Key

5 out of 5 average rating, 13 reviews

Home in Nokomis

Saltwater Oasis

A yellow two-story house is surrounded by lush tropical landscaping, featuring palm trees and shrubs. A balcony is visible above the entryway, which includes a decorative awning. The gravel driveway leads to the home, adding a rustic charm to the exterior.