Condo holiday rentals in Siesta Key

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, 148 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

A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.

4.92 out of 5 average rating, 114 reviews

The Honeymoon Suite on Siesta Key Beach

This is a recently renovated honeymoon suite located directly across from the big end of Siesta Key. It is an elegant ground floor pool unit. This unit is equip with marble countertops, tigers eye, lapis lazuli tables, bladeless ceiling fan, alabaster lighting and giant TVs. All of the appliances are stainless/smart and the microwave can cook steaks. There is a gym. The geographic location on the key can not be beat! There is a floating television over the California King luxury memory foam bed.

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, 142 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

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, 131 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, 398 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 ($35 per bike) King bed BEAUTY REST BLACK & queen sofa bed.

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.

4.85 out of 5 average rating, 102 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.

4.98 out of 5 average rating, 225 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: Open Thursday, March 26th!

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 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

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, 364 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.

4.88 out of 5 average rating, 127 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

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.

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

4.9 out of 5 average rating, 124 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 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! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

Popular amenities for Siesta Key condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

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.

4.92 out of 5 average rating, 83 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

The image captures a vibrant sunset over the horizon, casting warm hues across the sky. Palm trees line the foreground, creating a tropical ambiance. The view also includes a peaceful road and glimpses of the beach beyond, emphasizing the proximity to coastal scenery.

4.96 out of 5 average rating, 52 reviews

Siesta Key Beach front 2 bedroom condo w/ parking

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

Condo in Indian Beach-Sapphire Shores

A spacious patio provides a serene view overlooking Whitaker Bayou, with boats moored along the water. A round dining table, surrounded by white chairs, offers an inviting spot for meals while enjoying the scenery. The area is complemented by a colorful artwork piece on the wall.

5 out of 5 average rating, 13 reviews

Modern 1/1.5 Waterfront at The Strand

An aerial view captures a vibrant Siesta Key neighborhood, showcasing well-maintained homes amidst lush palm trees. The crystal-clear waters and white sandy beaches are visible in the distance, alongside the coastline dotted with beachgoers. Nearby, a mix of buildings emphasizes the area’s charm and accessibility.

4.96 out of 5 average rating, 54 reviews

Beach Rd, 300ft to Beach Access & 500ft to Village

A spacious living and dining area is illuminated by natural light. A modern dining set for six is positioned next to a comfortable seating area with a couch. Lush greenery is present in the corner, while large windows invite views of the outdoors.

4.92 out of 5 average rating, 64 reviews

Siesta Oceanview Retreat-1 min walking to 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, 74 reviews

Charming Siesta Key Condo Just Minutes from Beach

4.97 out of 5 average rating, 36 reviews

Condo in Sarasota

Charming Poolhouse · 1BR · Close to Siesta

Pet-friendly condo rentals

Superhost

The living area features a light-colored sofa complemented by an orange accent chair. A coffee table sits on a textured area rug, while wall art adds color to the red accent wall. Glass doors open to a view of outdoors, surrounded by greenery.

Condo in Gulf Gate Estates

4.91 out of 5 average rating, 138 reviews

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

Superhost

A spacious living area features a mix of comfortable seating, including a purple sofa and a black armchair. Large glass doors provide a view of the outdoor space and the surrounding landscape. A dining area is visible with a table set for four, accented by floral decor.

4.89 out of 5 average rating, 53 reviews

Dreamview • 1BR - Siesta Key Beach Sunset View

4.98 out of 5 average rating, 100 reviews

The living area features a seating arrangement with two blue sofas and a light coffee table. A ceiling fan is present, along with a beige recliner. Large glass doors open to a lanai, allowing natural light to fill the room, complemented by coastal-themed art on the walls.

Condo in Holmes Beach

A Coastal Retreat Steps From the Sea

4.95 out of 5 average rating, 107 reviews

A sandy pathway leads to the beach, framed by lush greenery and tall grasses. The gentle waves of the ocean are visible in the distance, with a clear blue sky overhead. Sunlight casts a warm glow on the pathway, inviting relaxation.

Condo in Venice

Short walk to beach 4, King bed, Dog Friendly

4.98 out of 5 average rating, 61 reviews

A sandy beach scene is presented, featuring a sign reading 'Siesta #1 Beach in the USA.' A palm tree stands nearby, offering shade, while a wooden bench invites visitors to sit and enjoy the view. The calm ocean is visible in the background under a clear blue sky.

Condo in Sarasota

SK condo heated pool & arcade, short walk to beach

4.97 out of 5 average rating, 198 reviews

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

Condo in Bradenton

Luxury 3/3 Margaritaville Resort

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.

4.83 out of 5 average rating, 133 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

4.96 out of 5 average rating, 103 reviews

Condo in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

Condo rentals with a pool

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.

4.98 out of 5 average rating, 64 reviews

2 BR condo in Siesta Key w/ Private beach access

The living area features two brown leather sofas flanking a wooden coffee table, with a decorative plant beside an illuminated lamp. Natural light enters through a large window, while a light blue wall and patterned rug enhance the comfortable surroundings.

4.94 out of 5 average rating, 51 reviews

Spectacular Siesta Key Beachfront Condo

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 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, 21 reviews

Siesta Key - Intracoastal, Pool & the Beach!

4.85 out of 5 average rating, 157 reviews

A cozy living area is depicted, featuring a comfortable sofa and two light blue armchairs. A wooden coffee table is centered in the space, while a small TV is positioned on a decorative cabinet. Soft lighting from floor lamps enhances the inviting atmosphere.

Condo in Sarasota

Siesta Key Ground Floor Condo 2BR On Trolley Line

A modern living space is showcased with a comfortable dark sofa and a round coffee table on a textured area rug. A dining table with four chairs is positioned nearby, while a large window offers a view of the ocean and natural light fills the room.

5 out of 5 average rating, 47 reviews

Amazing beach view! Entire unit renovated!

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.

4.94 out of 5 average rating, 48 reviews

Siesta Key condo - Gulf and bay club bayside