Apartment holiday rentals in Downtown Sarasota

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.

4.93 out of 5 average rating, 112 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 screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

4.97 out of 5 average rating, 126 reviews

A&A's Paradise near IMG & Anna Maria beaches

Conveniently located just 12 minutes drive from the beaches, close to IMG Academy and all amenities, this second floor corner condo has much to offer. Its picturesque lake view, modern upgrades, and spectacular open-concept design combine to enhance your vacation experience. Facilities at Shorewalk Palms include heated swimming pools, hot tubs, tennis court, basketball court, shuffle board court, pool table, ping pong table, BBQ area and a kid's playground. All are available for your enjoyment

A spacious studio features a cozy sleeping area with a queen bed dressed in soft linens, complemented by decorative pillows. Floor-to-ceiling windows provide natural light and a glimpse of the private garden. Soft earth tones create a calming atmosphere, and a textured rug adds warmth.

4.95 out of 5 average rating, 108 reviews

Hidden Gem Studio · Near Siesta Beach (5 min)

A true hidden gem just 5 minutes from Siesta Key Beach, this ground-floor studio offers a calm, comfortable stay in a highly convenient location. Ideal for couples or solo travelers looking for an easy Florida getaway with everything close by. Pet-friendly stay with a simple $10 one-time pet fee per booking. A perfect base for beach time, local dining, and unwinding at your own pace. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

Apartment in Longboat Key

4.98 out of 5 average rating, 222 reviews

Oceanfront LBK: Relax & Recharge!

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, 118 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, 133 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, 139 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

4.94 out of 5 average rating, 145 reviews

Apartment 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.

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, 355 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 serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.

4.94 out of 5 average rating, 160 reviews

Villa Maria: Minutes to Siesta Key!

2 BDRM/2 BTHRM condo very close to Siesta Key (3 min. drive or 20 min. walk). Totally UPDATED! Quality furnishings, super clean, ideal location. Have it all: Spacious condo in a peaceful setting. Just a few minutes drive over the south bridge to Siesta Key. Walking distance to great restaurants and shops on and off the key. Everything is within easy access by walking, car, bike, or free beach shuttle service. Come enjoy everything Sarasota has to offer.

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, 258 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.

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.

4.91 out of 5 average rating, 121 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 Downtown Sarasota apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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, 16 reviews

Luxe Waterfront Resort Style Living at its Best!

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.

4.87 out of 5 average rating, 23 reviews

New Luxury Waterfront Condo Pool/Gym/Hot tub

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!

4.94 out of 5 average rating, 18 reviews

Lanai w/ Pool Views • Minutes to Siesta Key

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, 32 reviews

Condo Downtown Sarasota. Sunsets, GYM, POOL/SPA

4.74 out of 5 average rating, 47 reviews

A living area is presented with a green sofa and a teal accent chair. A television is positioned on a stand, and bright natural light enters through two window frames. A patterned area rug complements the space, while a small side table offers additional surface area.

Apartment in Laurel Park

Downtown Sarasota #12

A spacious sleeping area displays two queen-size beds arranged with crisp white linens. A simple, modern decor is accentuated by a soft area rug. A vanity with a mirror and lamps can be seen in the background, complemented by a rustic sign that reads 'RELAX.'

4.84 out of 5 average rating, 45 reviews

Clean, cozy and very comfortable

A modern living area is featured with a plush beige sofa adorned with decorative pillows. A round coffee table sits in front, accompanied by a small dining table and chairs. Wall art and a circular mirror decorate the light-colored walls, while natural light filters through sheer curtains.

4.9 out of 5 average rating, 21 reviews

Sarasota Poolside Stylish Retreat w/Grill, Fishing

Pet-friendly apartment rentals

Apartment in Saint Armands

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.

4.92 out of 5 average rating, 73 reviews

Steps from Lido Beach & St. Armands Circle

Apartment in Bradenton Beach

4.87 out of 5 average rating, 39 reviews

Tradewinds Deluxe North Cottage

4.88 out of 5 average rating, 57 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.

Apartment in Cove

J&J Island Time

A modern waterfront condominium complex is set along a tranquil canal, featuring multiple levels with balconies. Well-maintained pathways lead to docks lined with boats, surrounded by lush greenery. A colorful sunset casts a warm glow across the building's facade and the water.

5 out of 5 average rating, 15 reviews

The Strand, Luxury Condo, Breathtaking Water Views

4.98 out of 5 average rating, 61 reviews

Siesta Key w heated pool arcade & pet friendly

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.

4.97 out of 5 average rating, 195 reviews

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, 129 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

Apartment in Holmes Beach

4.96 out of 5 average rating, 101 reviews

Steps to the beach! Condo with pool at The Terrace

Apartment rentals with a pool

4.87 out of 5 average rating, 68 reviews

Cozy Top-Floor Stay on Siesta Key

A heated swimming pool is surrounded by a spacious deck with lounge chairs. A shaded cabana is visible to one side, enhancing the inviting atmosphere. Palm trees and lush landscaping create a tropical ambiance under a clear blue sky.

4.74 out of 5 average rating, 141 reviews

Best Deals on Siesta Key

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, 38 reviews

Chill Sarasota Hideaway

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!

5 out of 5 average rating, 9 reviews

Luxury 2BR/2BA Condo Minutes from Beaches & IMG

Apartment in Longboat Key

A spacious sleeping area features a plush king bed with silky white linens and decorative blue accents. A blue ottoman sits at the foot of the bed, while a large TV is placed on a dark wood dresser. Natural light filters in through the nearby balcony doors.

5 out of 5 average rating, 8 reviews

Waterfront Coastal Retreat | Steps from LBK Beach

A cozy lanai features a view of the tranquil lake, with vibrant turquoise chairs arranged around a patterned rug. Potted plants add greenery, while large glass doors provide natural light and an outdoor connection.

4.95 out of 5 average rating, 190 reviews

The Seashell Cottage with peaceful water views!