Condo vacation rentals in South Sarasota

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, 413 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.

4.98 out of 5 average rating, 126 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

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, 105 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, 237 reviews

Condo in Longboat Key

Island Time on LBK: Open Sunday $175/nt + Fees!

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 light-filled living area features a comfortable white sectional sofa with decorative pillows, complemented by a wooden coffee table. Large glass doors lead to an outdoor space, while a television and two lamps enhance the room's functionality and warmth.

4.85 out of 5 average rating, 123 reviews

The Palm Bay Club on Siesta key Beach

Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

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, 150 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!

The kitchen features modern appliances including a stainless steel refrigerator, an oven, and a microwave. White cabinetry complements the granite countertops, while pendant lighting provides illumination. A breakfast bar with white stools offers an inviting space for casual dining.

4.91 out of 5 average rating, 129 reviews

Oceans2

Perfectly nestled between the soft white sands of the Gulf of Mexico and the calm, sparkling waters of the bay, this premier condo offers the absolute best of the coastal Florida lifestyle. Whether you are looking for a relaxing sun-drenched getaway, a boater’s paradise, or an active island adventure, this beautifully situated property serves as your perfect home base. From the moment you arrive, you will experience the effortless charm and convenience of island living at its finest.

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, 378 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.

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, 132 reviews

Siesta Key For Me @ The Palm Bay Club

🏖️ Newly Renovated Siesta Key Condo | Ocean + Bay Views | Sleeps 6 📍 Bayside Suite at The Palm Bay Club | Walk to Beach ✨ ALL-NEW RENOVATIONS MAY 2025! Brand new bathrooms, flooring, doors, trim, granite countertops & more—be among the first to enjoy our stylish upgrade! Welcome to Condo #310 at The Palm Bay Club—a 2BR/2BA bright and breezy bayside condo with water views, modern upgrades, and private beach access just a short walk away. Sleeps up to 6 guests comfortably.

Condo in Gulf Gate Estates

4.96 out of 5 average rating, 135 reviews

Modern Studio · 5 min from Siesta Beach

Stylish ground-floor studio designed for couples or solo travelers, just a 5-minute drive from world-famous Siesta Key Beach. A great choice if you’re looking for a calm, well-located space with thoughtful comfort. Pet-friendly stay – $10 one-time pet fee per booking, unlimited pets. An ideal base for beach days, local dining, or a relaxed Florida getaway. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

4.92 out of 5 average rating, 161 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!

5 out of 5 average rating, 106 reviews

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Whisk your favorite person away to BayDreaming! Retreat to this quiet 1BR/1.5BA condo, just an 8‑minute walk from Turtle Beach. Perfect for couples, it offers a private deck with canal and Gulf views, a heated pool for sunset swims, two supyaks, and a plush king bed for cozy nights. Enjoy garage parking, beach gear, and a peaceful community. Whether you’re here to relax or reconnect, this coastal retreat blends romance with Siesta Key serenity.

Popular amenities for South Sarasota condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

A bright kitchen and dining area feature a long granite countertop with bar seating for four. A dining table seats six, with fresh fruit displayed centrally. Floor-to-ceiling sliding doors open to a patio overlooking the beach, inviting natural light and ocean views.

5 out of 5 average rating, 9 reviews

2BR Penthouse - Stunning Beach Views on Siesta Key

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, 15 reviews

Modern 1/1.5 Waterfront at The Strand

4.9 out of 5 average rating, 20 reviews

Beautifully Remodeled Stylish Condo in Sarasota

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

A spacious living area features a blend of leather seating and a coffee table, with light wood accents. A dining table for four is seen in the background, accompanied by chairs. Outdoor light filters in through a nearby entryway, enhancing the open atmosphere.

4.9 out of 5 average rating, 39 reviews

Beautifully Furnished Turnkey Sea Winds rental

The exterior of a ground floor condo is shown, featuring a white picket fence and stone steps leading to a private entrance. Lush greenery and palm trees frame the surroundings, creating a tranquil outdoor setting.

4.89 out of 5 average rating, 74 reviews

* Beautiful 1BR Beach Condo minutes to Gulf *

An open-concept kitchen and dining area features a spacious bar with modern stools. Natural light brightens the room, highlighting the sleek appliances and clean lines of the white cabinetry. A dining table is visible, with a warm wood floor adding to the inviting ambiance.

4.97 out of 5 average rating, 34 reviews

Lovely two bedroom Condo

4.96 out of 5 average rating, 51 reviews

bayside condo, deeded beach access, heated pool

Pet-friendly condo rentals

An expansive wrap-around balcony presents a dining table set for four, featuring elegant tableware. The tranquil waterfront views showcase a colorful sunset sky, reflecting on the water. Lush greenery surrounds the area, enhancing the serene ambiance of the outdoor space.

5 out of 5 average rating, 4 reviews

Waterfront, Resort Pool / Spa, & Fitness Center!

4.95 out of 5 average rating, 111 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

4.96 out of 5 average rating, 74 reviews

Perfect location 2 BR condo w pool arcade pets ok

4.97 out of 5 average rating, 206 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.

4.84 out of 5 average rating, 141 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

Condo in Gulf Gate Estates

4.91 out of 5 average rating, 54 reviews

Updated condo minutes to Siesta Key Beach

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, 34 reviews

Condo Downtown Sarasota. Sunsets, GYM, POOL/SPA

A dining area is shown with a round table surrounded by four chairs beneath a ceiling fan. A playful sunflower painting adorns the wall, while a small potted plant adds a touch of greenery. The space is illuminated by natural light from nearby windows.

4.64 out of 5 average rating, 47 reviews

Downtown Sarasota #11

Condo rentals with a pool

An aerial view captures the expansive white sand beach and turquoise waters, lined with beachgoers. The surrounding buildings and amenities are visible, including pools and recreational areas, creating a vibrant coastal atmosphere. Cloud patterns add depth to the bright blue sky above.

4.94 out of 5 average rating, 129 reviews

Beautiful White Sand Siesta Key Beach

4.92 out of 5 average rating, 158 reviews

Gulf Views | Walkable | Spacious

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, 58 reviews

Siesta Dunes 1st Floor Beach Front Retreat

Condo in Gulf Gate Estates

A spacious living area features a gray sofa and armchair, accented by bright orange and yellow decorative elements. A large window brings in natural light, showcasing a view of greenery. A vibrant area rug adds color, while a media console and coffee table complete the setting.

4.87 out of 5 average rating, 75 reviews

The Perfect Shiny Oasis

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, 144 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

5 out of 5 average rating, 3 reviews

Peaceful Siesta Key Retreat, Heated Pool, Tennis

4.55 out of 5 average rating, 11 reviews

2BR Beach Club – Beach, Heated Pool & Hot Tub

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.