Vacation rentals in Lido Key

4.97 out of 5 average rating, 101 reviews

A dining area features a wooden table surrounded by six chairs with patterned cushions. A fireplace is located on a white brick wall, while an open kitchen is visible in the background. Bright lighting enhances the airy feel, complemented by wood beamed ceilings.

Home in Sarasota

Lido Beach Dream

Bright and sunny remodeled and updated beach home featuring wood beamed ceilings, new bamboo wood firs, with 3 good size bdrms, 2 full baths, , master with with en suite, 2 queen beds, 2 twin beds,open and airy kitchen w/ eating bar and table to seat 6 plus , new appliances, w/d, large family rmwith fireplace, huge year round air conditioned lanai, garage. Golf, sailing, walking & bike trails. Walk to St Armand's Circle, beach, heated pool block away, restaurants, 130 stores and spec. shops.

The rooftop deck features an inviting area with beach-style lounge chairs under a thatched umbrella. Green synthetic grass provides a cozy feel, complemented by potted flowers, offering a serene spot for relaxation and enjoying the outdoor atmosphere.

4.93 out of 5 average rating, 101 reviews

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach

Step into your WINTER Holiday with a Beach Vacation! Now booking Spring! Reserve your March & April dates! Picture this: a rooftop deck, just a 5min walk to the pristine sand of Lido Beach, and surrounded by the charm St Armand's Circle with boutiques, and eateries, all within walking distance. Forget the conventional - this condo's got a secret. Tucked behind an unassuming door lies a vibrant space, drawing inspiration from speakeasy culture fused w/ a beach vibe. Your adventure starts now

4.9 out of 5 average rating, 218 reviews

A spacious living area is highlighted by a large sectional sofa and a wooden coffee table. A TV sits atop a media console, while glass doors provide access to the outdoor patio, allowing natural light to fill the room.

Villa in Sarasota

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

4.99 out of 5 average rating, 198 reviews

A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

A cozy sleeping area features a spacious bed adorned with dark blue and cream pillows. Natural light filters in through glass doors, reflecting off a mirrored closet. A serene beach photograph is displayed on the wall, complementing the light grey walls and wooden flooring.

4.9 out of 5 average rating, 62 reviews

Lido-Key-Tiny Adorable Studio-C

**No Kids Allowed**Lido-Key-Newly remodeled tiny (smaller than a hotel room) Studio. 7-10 min walk to the beach & St.Armands Circle. Quaint main floor studio in a great location. This is an affordable way to enjoy this popular area. This cozy cottage features a Queen bed, refrigerator, stove, microwave, coffee maker, fully stocked cooking items & dishes & beach towels, chairs, & cart. 170 Roosevelt Dr., Sarasota. Enjoy this centrally-located place.

5 out of 5 average rating, 29 reviews

A private pool is surrounded by lush tropical foliage, creating a serene atmosphere. A waterfall feature can be seen cascading into the clear water. Colorful plants, including vibrant bougainvillea, enhance the natural beauty of the outdoor space.

Home in Sarasota

Walk to Lido Beach &St. Armands -grill/HEATED POOL

A piece of paradise! Walk one block to the beach, 5-minute walk to St. Armands! HEATED POOL, 2BR w/grill. This beautiful home, nestled on a little piece of paradise, is just a stone's throw from Lido Beach! A perfect place to relax, unwind and enjoy your private, mature lush surroundings. This charming home has incredible internet, with 457 mbps download and 28 mbps upload speeds. It also has crown moldings and four ceiling fans.

A studio apartment features a king bed against a light wall, complemented by a cozy seating area with a gray sofa and a chair nearby. Two round coffee tables sit on a neutral rug, with a wall-mounted smart TV and built-in shelves adding practical style.

4.98 out of 5 average rating, 174 reviews

Studio Minutes to Siesta key, Lido Key, and SMH!

Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes

4.97 out of 5 average rating, 114 reviews

The guesthouse bedroom features a spacious bed covered with a patterned comforter in blue and white tones. A dresser and a wall-mounted TV are visible, and light-colored flooring enhances the room's airy feel. A door leads to an adjoining living area.

Guest suite in Sarasota

Lido Beach Guest House - Chasing the Sun

Adorable 1 Bedroom, 1 Bath guesthouse less than a block to Lido Beach and St Armands circle. Enjoy a morning stroll on the beach collecting sea shells, walk to St. Armand's to experience great restaurants and shopping or enjoy a day kayaking or lounging on the beach. This vacation home has all of this and more just waiting for you to experience! Certificate of Registration Number VR22-00021

4.97 out of 5 average rating, 340 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

Huge NOV SALE, EXCL Sarasota #1 Luxery beach Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

An inviting entrance to the beach cottage is framed by lush green landscaping and vibrant flowers. A wooden sign reading 'Beach House' is prominently featured above a natural pathway leading towards the inviting front door.

4.96 out of 5 average rating, 54 reviews

The One Bedroom

Sarasota Magazine quotes our beach cottage as " fresh and bright with a mid-century vibe that welcomes guests from all over the world." The city requires a 7 day minimum stay but please contact us regarding shorter stays as we are happy to block out the remaining days to accommodate your dates and allow you to stay with up whilst keeping to the rules.

4.93 out of 5 average rating, 116 reviews

A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.

Home in Sarasota

St Armand's Mid-Century Oasis

Mid-century retreat in the heart of Lido Key! Stroll to pristine beaches or enjoy the vibrant shops & eateries of St. Armand's Circle just steps away! Recently renovated with authentic period details, this 3BR/3BA gem boasts a sparkling pool, sun-soaked rooftop deck and stylish office.