Condo vacation rentals in South Sarasota

A spacious living area is highlighted by a light-colored sectional sofa adorned with colorful pillows. A large coffee table is positioned in front of the sofa, and a dining table with six chairs is visible in the background. A fan hangs from the ceiling, and natural light enters through nearby windows.

4.97 out of 5 average rating, 117 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.

4.85 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.

4.95 out of 5 average rating, 143 reviews

A charming studio space features a queen size bed with a white blanket and decorative pillows. A small nightstand sits beside the bed, and a light is positioned for reading. Natural light enters through a large window with blinds, complementing the wood-look flooring.

Condo in Lido Key

Lido-Key- Tiny Studio Holiday Cottage-A

We are Open after Hurricane Helene! **No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

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.

4.9 out of 5 average rating, 100 reviews

Oceans2

This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki hut, or try your luck on the fishing pier, all while viewing the boats on the intercoastal as they pass by. Included is a private deeded beach access that is an easy 5 min walk . Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. Boat slip available for up to 24' .

A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.

4.85 out of 5 average rating, 131 reviews

Anchor house +6 min. from Siesta Beach+heated pool

★ "Ground floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key Heated Pool! Welcome to your perfect Sarasota getaway! This 600 sq. ft. pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

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.

4.85 out of 5 average rating, 252 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, 148 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!

A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.

4.97 out of 5 average rating, 211 reviews

Gateway to Siesta Key - 1/2 Mile to the Beach

Beautiful and comfy 2 bedroom/2 bathroom condo that sleeps 4. The condo is located only 1/2 mile from the Gulf Of Mexico. Spacious, comfortable, in a small & quiet complex that provides easy access to restaurants and stores on or off Siesta Key. You'll get super easy Siesta Key access (3 min drive/20 min walk) at a very affordable price in a perfect location to avoid traffic and enjoy the rest of Sarasota when you're not at the beach.

The outdoor area features several lounge chairs and umbrellas arranged around a clean patio, with well-maintained landscaping in the background. A pathway leads toward the ocean, where turquoise waters can be seen in the distance under clear skies.

4.97 out of 5 average rating, 110 reviews

203 Luxury Condo With Ocean View, Heated Pool +

Luxurious apartment style condo on Siesta Key Beach, Sarasota Florida overlooking the quartz white sand and turquoise waters of the #1 beach in the USA. Enjoy exquisite ocean views from the balcony or just a few steps to the beach. Our gated community positions you steps away from whatever your heart desires (pool, ocean, grocery store, restaurants, live music and local shops). Your options are limitless on Siesta Key.

The studio features a modern kitchen with white cabinetry and a large countertop. A flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors that lead to the private garden. A compact dining table and a plush blue ottoman add functionality.

4.97 out of 5 average rating, 102 reviews

Blue studio perfect for 2, just 5 min from beach

Ground floor studio" ★ "An incredible studio and 6 star hospitality!" Welcome to your perfect Sarasota getaway! This is pet-friendly home offers a garden and a prime location just 5 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

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.

4.86 out of 5 average rating, 152 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

A cozy Siesta Key ground floor condo unit w 2 bedrooms & 1 bath on the trolley line. Has all the amenities you need for a relaxing beach vacation and your day at the beach. Located conveniently to Crescent beach w access to the south and Siesta Key public beach to the north. Trolley stops right out front. Assigned parking spot directly in front of the unit.

The living room features a spacious layout with a comfortable gray sofa and rocker recliner. A dining area with a table for six is present, alongside large glass doors that provide ample natural light and a view of the surrounding greenery. A flat screen TV is visible.

4.97 out of 5 average rating, 129 reviews

Siesta Key Condo. Checkout our great rates!

Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.

Popular amenities for South Sarasota condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

Condo in Indian Beach-Sapphire Shores

A spacious pool area is surrounded by modern buildings, featuring lounge chairs arranged around the water's edge. The pool, shaped in a gentle curve, invites relaxation under a clear blue sky with a few scattered clouds.

5 out of 5 average rating, 15 reviews

Luxe Waterfront Resort Style Living at its Best!

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.

5 out of 5 average rating, 21 reviews

Just renovated 2bed/2bath Siesta Key Beach Condo

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.

4.86 out of 5 average rating, 72 reviews

The Perfect Shiny Oasis

A bright studio space features a queen-sized bed next to a comfortable grey sofa. Natural light filters through sliding glass doors that lead to a private balcony. A well-equipped kitchen with modern appliances is set against a stylish backsplash, enhancing the inviting atmosphere.

4.96 out of 5 average rating, 56 reviews

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

Condo in Indian Beach-Sapphire Shores

A circular pool is surrounded by modern white buildings, with palm trees dotting the perimeter. The clear blue water reflects the sky, and a poolside lounge chair is positioned near the edge. Paved stones create a pathway around the pool area.

5 out of 5 average rating, 34 reviews

Chill Sarasota Hideaway

4.9 out of 5 average rating, 50 reviews

Updated condo minutes to Siesta Key Beach

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, 43 reviews

Amazing beach view! Entire unit renovated!

An outdoor patio area features a seating arrangement with plush cushions and a glass coffee table, set against a backdrop of palm trees. A shared heated pool is visible, surrounded by a mix of tropical foliage, creating a relaxed and inviting environment.

4.9 out of 5 average rating, 20 reviews

100 ft to Beach – 1BR Siesta Key Escape

Pet-friendly condo rentals

4.92 out of 5 average rating, 71 reviews

The image captures a shared pool area surrounded by lush greenery and palm trees. Lounge chairs with blue umbrellas are positioned around the pool, which is enclosed with a white fence. A pathway leads through well-maintained landscaping, enhancing the inviting outdoor space.

Condo in Saint Armands

Steps from Lido Beach & St. Armands Circle

4.87 out of 5 average rating, 54 reviews

A light-filled living area is furnished with a curved sectional sofa adorned with colorful cushions. A round coffee table rests on a floral-patterned rug, surrounded by decorative plants and coastal-themed artwork. Large sliding doors lead to an outdoor space, framed by sheer curtains.

Condo in Cove

J&J Island Time

4.96 out of 5 average rating, 99 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

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, 50 reviews

Siesta Key with heated pool arcade & pet friendly

4.98 out of 5 average rating, 191 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, 119 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

4.96 out of 5 average rating, 99 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

4.75 out of 5 average rating, 8 reviews

Star Fish - 1125

Condo rentals with a pool

A modern outdoor pool area features a spacious pool surrounded by lounge chairs. A building with large windows is seen in the background, complemented by landscaped greenery and palm trees. The clear sky above enhances the inviting atmosphere of this recreational space.

4.86 out of 5 average rating, 22 reviews

New Luxury Waterfront Condo Pool/Gym/Hot tub

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, 347 reviews

On the Beach; Siesta Key SunBum Studio

A serene beach scene captures calm waves gently lapping at the shore under a sky filled with scattered clouds. Soft hues of orange and blue reflect in the water, suggesting an approaching sunset over the tranquil coastline.

4.85 out of 5 average rating, 82 reviews

Private Beach Access. Pool. Grill. Siesta Key

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

A spacious living and dining area is displayed, featuring a wooden dining table surrounded by six white chairs. A dark leather sofa sits opposite, with natural light flowing in from large windows surrounded by greenery. Decorative plants and artwork are present, creating a cozy environment.

4.96 out of 5 average rating, 75 reviews

Peaceful retreat, pool, hot tub, near Siesta Key!

An expansive view showcases the Gulf waters and sandy beach from a fourth-floor corner unit. Lounge chairs are visible on the beach, while a balcony railing frames the scene. Bright skies are complemented by gentle waves rolling onto the shore.

4.93 out of 5 average rating, 74 reviews

Beach & Pool Open! Direct Beachfront Condo! Sunset

A view of the beach is captured from a balcony, showcasing the expanse of the Gulf of Mexico and the white sandy shore. Lush green landscaping lines the pathway leading to the beach, framed by palm trees. Sunlight illuminates the scene, accentuating the tranquil atmosphere.

4.95 out of 5 average rating, 44 reviews

Siesta Key Beachfront Condo - Private beach access

A sunset view shows the calm ocean meeting the horizon, with soft orange and pink skies. The coastal area is framed by several low-rise buildings and lush palm trees, creating a serene atmosphere. Traffic lights and roads are visible in the foreground, leading toward the beach access.