Condo holiday rentals in Siesta Key

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.

4.93 out of 5 average rating, 122 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.

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, 100 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.

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, 126 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 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, 135 reviews

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

Welcome to beautiful 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 heated swimming pool is centrally located, surrounded by colorful lounge chairs in red, yellow, and green. The turquoise water is inviting under clear blue skies, with palm trees bordering the area. Nearby, several outdoor chairs are positioned for relaxation.

4.91 out of 5 average rating, 243 reviews

Near beach. Daily rentals. Pool. king bed

Villa 1 is a ground floor end unit. You have your own private entrance. With self check in key pad Featuring 1 bedroom, 1 bathroom, large living room with SMART TV, A/C, Kitchenette with stainless steel appliances ,Granite counter tops, Fridge Freezer. Separate bedroom with King Bed, Free wifi .Free parking for 1 vehicle. Shared swimming pool. Daily and weekly rentals. 2 mins walk to Crescent beach Siesta Key Beach Access #13 No smoking $250 Fee No pets $250 Fee No bikes inside rental.

Aerial view showcasing a sandy beach surrounded by vibrant turquoise waters. Lush greenery is visible along the shoreline, with boats floating in the clear water. The scene captures a serene coastline, inviting guests to explore the natural beauty.

4.93 out of 5 average rating, 207 reviews

Steps away from beach and village! #1 in Siesta!

The Little Sandy... Your secret hideaway Incredibly located Two bedrooms, one bath Sleeps 6 easily Bring the kids...or not Walk everywhere. 3-minutes to the beach, 8 to Siesta Village Super-fast Wi-fi! Icy A/C Lovely pool Play in the water, play on the sand, play in the village Rinse and repeat Comfy beds, soft towels A great night's sleep And the best hosts on Airbnb Tradewinds included free of charge. So book now and find your Siesta-self Just like you, only funner.

A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.

4.95 out of 5 average rating, 106 reviews

Seaside on Siesta Key Beach

Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street Siesta Key Beach. NEWLY RENOVATED in 2025. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village. First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

4.98 out of 5 average rating, 218 reviews

Condo in Longboat Key

Oceanfront Open Mon - Fri, $185/nt + Fees!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located 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 onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort!

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, 348 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. Enjoy 2 free bikes day rental with booking!

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.

4.96 out of 5 average rating, 113 reviews

Palm Bay Club! Resort Style 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 living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

4.84 out of 5 average rating, 255 reviews

Cozy 1BR Beach Condo on Siesta Key!

Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

4.92 out of 5 average rating, 149 reviews

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!

Popular amenities for Siesta Key condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo 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.

4.98 out of 5 average rating, 59 reviews

2 BR condo in Siesta Key w/ Private beach access

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, 73 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

A view from the balcony captures the expansive beach and vibrant turquoise waters. Sun loungers are arranged on the soft, white sand below, framed by gently swaying palm trees. The clear blue sky stretches overhead, enhancing the sense of spaciousness and serenity.

4.84 out of 5 average rating, 19 reviews

Unmatched Gulf Views | Stunning 5th-Floor Condo

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, 51 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

5 out of 5 average rating, 18 reviews

Poolhouse 1/1, 4 min from Siesta

5 out of 5 average rating, 14 reviews

Your Beachside King Suite Retreat!

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, 68 reviews

Breathtaking Beachfront Views in Siesta Key

A light-filled living room features a comfortable navy sofa with decorative cushions, a patterned armchair, and a round accent table. A coffee table rests on a woven rug, while built-in shelves display books. Soft lighting is provided by stylish pendant fixtures and table lamps.

4.94 out of 5 average rating, 67 reviews

1 Bed Cottage, Full Remodel, Beach Access #7, Walk

Pet-friendly condo rentals

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.

4.88 out of 5 average rating, 52 reviews

Dreamview • 1BR - Siesta Key Beach Sunset View

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.

4.98 out of 5 average rating, 53 reviews

Siesta Key w heated pool arcade & pet friendly

4.98 out of 5 average rating, 194 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.

4.86 out of 5 average rating, 121 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

Superhost

A sign marking Siesta Beach as the '#1 Beach in the USA' is prominently displayed at the entrance. A sandy pathway leads to the beach, flanked by green vegetation and palm trees. Beachgoers and colorful umbrellas can be seen in the background, emphasizing the lively atmosphere.

4.89 out of 5 average rating, 70 reviews

A Hidden Gem in Paradise

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

4.89 out of 5 average rating, 160 reviews

6 min to Siesta Beach | Heated Pool | Lake View

Condo in Indian Beach-Sapphire Shores

The living space features a modern open floor plan with a comfortable blue sofa and a dining area with a stylish light fixture above. A large window provides natural light, and various decorative elements, including plants and wall art, enhance the ambiance.

4.94 out of 5 average rating, 31 reviews

Condo Downtown Sarasota. Sunsets, GYM, POOL/SPA

Condo in Indian Beach-Sapphire Shores

The view from the patio overlooks Whitaker Bayou, featuring calm waters lined with lush greenery and docks. Sunlight reflects off the water's surface, creating a serene atmosphere. The image captures a tranquil waterfront scene, enhancing the natural beauty of the surroundings.

5 out of 5 average rating, 10 reviews

Charming Waterfront 1/1.5 Beautiful Sunsets!

Condo rentals with a pool

A cozy deck area features outdoor seating with two bar stools and a small table adorned with flowers. Palm trees provide shade while a serene waterfront view is visible, with a private dock and a pool in the background.

4.98 out of 5 average rating, 51 reviews

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

Superhost

5 out of 5 average rating, 5 reviews

Escape the Cold: Enjoy 20% Off Your Beach Getaway!

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.

4.93 out of 5 average rating, 159 reviews

Siesta Key Serenity At The Palm Bay Club

The heated pool is bordered by a stone patio and surrounded by lush greenery. Umbrellas and lounge chairs provide seating options. A tiki bar is visible in the background, with a scenic view of the water and distant trees, creating a relaxing outdoor space.

4.95 out of 5 average rating, 22 reviews

Just renovated 2bed/2bath Siesta Key Beach Condo

An aerial view showcases the waterfront property, highlighting the building's proximity to the canal. Nearby greenery and water feature prominently, while the surrounding area includes various residential and commercial structures, indicating a vibrant community. The pool is visible, situated on the property.

4.93 out of 5 average rating, 27 reviews

Waterfront w/ Pool, mins to SK Beaches, bikes/sups

5 out of 5 average rating, 15 reviews

An updated kitchen features sleek white cabinetry and modern stainless steel appliances. A spacious island provides additional counter space. Stylish lighting fixtures hang from the ceiling, while a decorative mirror and lamp enhance the room's design. Subtle textures and finishes add to the contemporary feel.

Condo in Venice

Location! Gulf Condo @ S. Jetty 30 day minimum

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

The exterior of a multi-story villa is showcased, featuring a light-colored facade and multiple balconies with railings. Lush palm trees are positioned in front, and the entrance is framed by decorative lights. The scene is set against a vibrant dusk sky.