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, 156 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

4.89 out of 5 average rating, 107 reviews

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

4.8 out of 5 average rating, 198 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

4.96 out of 5 average rating, 111 reviews

Sun-filled cottage with pool, walk to beach

Welcome to Palm Cottage. Our space is the perfect cozy getaway for any time of year. Recently renovated three bedrooms and one bathroom make this the perfect spot for two couples or a family. The private backyard includes a brand new pool with a hot tub and a sun shelf, as well as outdoor dining area and fire table. Enjoy a leisurely stroll to Siesta Key to play at the beach or grab a meal at one of the many restaurants. Home includes two bikes and all the gear you need for a day 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.

4.88 out of 5 average rating, 146 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.

4.95 out of 5 average rating, 146 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.

A light-filled bathroom is visible, featuring a modern sink with a glass basin. Towels are neatly hung on the wall. A doorway leads to a bedroom with a spacious bed, complemented by a ceiling fan and natural light flowing through a large window.

4.85 out of 5 average rating, 428 reviews

[Sunny in Siesta] King bed+5 minute walk to beach

Your relaxing beach vacation awaits! Enjoy the island life from a freshly remodeled condo. Quick stroll to the #1 beach in the US. Public Access #12 (5 min walk) or hop on the free trolley to Siesta Beach & the Village. Can’t beat this location...Walk to Crescent Club, Captain Curt’s, Big Water Fish Market, Daquiri Deck & more. Beach gear includes- wagon., 2 chairs, small cooler and beach towels. 2 Bikes available to rent (40 per bike) King bed BEAUTY REST BLACK & queen sofa bed.

4.99 out of 5 average rating, 114 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.

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.

4.96 out of 5 average rating, 159 reviews

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, 134 reviews

Private Beach with Loungers · 2 Pools & Bay Views

Beachside convenience for families, groups and remote workers who want effortless sand days and active resort living. This oversized renovated 2‑bed, 2‑bath condo in a gulf-to-bay complex offers bay views, two heated pools and a heated spa, on-site gym and courts, provided beach chairs, umbrella and wagon, free parking and keypad self check-in. Walk to Siesta Key Beach and catch the island trolley steps away for dining and shops.

A dining table is set with elegant glassware and neutral tableware. A decorative figurine of a crane stands between two tall candlesticks, with a soft ocean view visible through the screened lanai in the background.

4.92 out of 5 average rating, 102 reviews

Siesta Key Oasis with Gulf Views

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 5th floor unit has an extra large lanai that provides some of the best Gulf views on Siesta Key! 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year!

4.98 out of 5 average rating, 125 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 private beachfront terrace offers sweeping views of the Gulf, where soft sand and palm trees are visible. Comfortable seating is arranged on the patio, complemented by a coffee table and a round dining table, all under a ceiling fan and wooden overhang.

4.88 out of 5 average rating, 8 reviews

Direct Gulf View - Residence 307

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, 172 reviews

Siesta Key Serenity At The Palm Bay Club

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, 63 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, 138 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, 392 reviews

On the Beach; Siesta Key SunBum Studio

4.82 out of 5 average rating, 111 reviews

LJ's Cottage 2

4.96 out of 5 average rating, 23 reviews

Siesta Bliss ~ Luxury Waterfront Retreat

Family- and pet-friendly home rentals

5 out of 5 average rating, 17 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, 33 reviews

Penthouse Beautiful Ocean Views

4.98 out of 5 average rating, 40 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

5 out of 5 average rating, 4 reviews

4 bed, 5 bath, private pool home and apartment

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, 133 reviews

Siesta Beach View : Pineapple Bungalow Efficiency

5 out of 5 average rating, 3 reviews

6630B - Mira Bella

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 251 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

5 out of 5 average rating, 11 reviews

Apartment in Siesta Key

Siesta Key Luxury Penthouse, walk to Beach&Village

Family-friendly home rentals with a pool

5 out of 5 average rating, 34 reviews

Beach Villa w Garage | Extra Space

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, 107 reviews

Private Standalone Home - Walk to Siesta Key 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!

5 out of 5 average rating, 6 reviews

Villa in Sarasota

Siesta Key*GULF SIDE oasis*PRIVATE BEACH*Pool

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, 174 reviews

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

4.88 out of 5 average rating, 345 reviews

A charming yellow cottage is set against a clear blue sky, featuring a welcoming porch with wooden steps leading up to it. Surrounding palm trees contribute to the relaxed ambiance of the outdoor space.

Cottage in Siesta Key

Cottage on Siesta Key Beach

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.

4.9 out of 5 average rating, 21 reviews

Condo on Siesta Beach with a view!

4.92 out of 5 average rating, 167 reviews

Cottage on Siesta Key Beachside & Stunning sunsets

Family-friendly home rentals with Wifi

5 out of 5 average rating, 3 reviews

Luxury Beachfront Home at #1 Beach in USA

4.84 out of 5 average rating, 94 reviews

A charming villa features a red-tiled roof and white exterior, surrounded by lush greenery and palm trees. A front porch with screens invites light while colorful chairs provide a welcoming touch. The paved pathway leads directly to the entrance, offering easy access.

Cottage in Sarasota

Fiesta On Siesta

5 out of 5 average rating, 7 reviews

Siesta Key Villa | Pool + Free Daily Activities

5 out of 5 average rating, 14 reviews

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

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 spacious dining area is presented with a round glass table surrounded by dark wooden chairs. A modern light fixture hangs above, illuminating the area. The kitchen features white cabinetry, stainless steel appliances, and a large island with bar stools, creating a welcoming and functional space.

4.96 out of 5 average rating, 76 reviews

Siesta Key Spacious, Modern 2 bed, 2 bath condo

4.93 out of 5 average rating, 14 reviews

Apartment in Sarasota

Parrots beach bungalow

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.