Vacation rentals with a pool in Lido Key

5 out of 5 average rating, 6 reviews

3BR/2BA beach villa on Lido Key

Treat yourself to an unforgettable vacation at a luxury modern villa at the perfect location of Lido Beach. Walking distance from St Armand’s Circle, a sophisticated outdoor dining and shopping area with distinct European flair, iconic examples of mid century modern architecture and the turquoise waters of the Gulf of Mexico. Here you can find some of the best coastal and ethnic restaurants, live entertainment, high end fashion and jewelry boutiques, spas, art galleries, gift shops, kids arcade

5 out of 5 average rating, 6 reviews

Luxe Lido Key Escape with Private Pool

Exclusive Amenities Include: • Walking Distance to St. Armands Circle • Less than 0.3 miles to Lido Key Beach • Private Heated Pool • Fire Pit • Ping Pong Table • 5 Bedrooms, 4.5 Bathrooms • Private Parking • Free WiFi & HD Smart TV’s • Regular & Keurig Coffee Maker • Beach Towels, Chairs, Cooler, & Caddy Provided • Enhanced CleaningProvided by our CottageClean Team • Privacy Wall • Proximity to SRQ Airport and Downtown Sarasota • Dog Friendly (1 dog up to 25 lbs with an additional fee)

5 out of 5 average rating, 22 reviews

Sarasota Escape | Minutes to Beaches + Downtown

HEATED POOL. NONTOXIC + ECO FRIENDLY. Relax with the whole family or bring that group chat trip to life at this peaceful retreat in the heart of Sarasota. Boasting a spacious and nature-inspired design, this home is a short drive to several world class beaches, the downtown Sarasota arts district, 5 star dining, shopping and more. The home is also located within walking distance of a park complete with playground, public pool, tennis + basketball courts, workout area and walking trails.

4.89 out of 5 average rating, 81 reviews

Condo in Sarasota

Lido-Key- Tiny, Yet Charming Studio-B

We are Open after Hurricane Helene! **No Kids Alllowed**. Lido-Key- Newly remodeled TINY (smaller than a hotel room) Studio. 7-10 min walk to the beach and St.Armands Circle. Quaint main floor tiny 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, along with beach chairs, towels, & cart. Located at 170 Roosevelt Dr., Sarasota

4.93 out of 5 average rating, 123 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

4.95 out of 5 average rating, 210 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown and more. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack.

4.87 out of 5 average rating, 101 reviews

Condo in Siesta Key

Siesta Key Condo: Beach, Pool & Village Fun!

Escape to paradise in our newly renovated 2-bedroom condo, perfectly situated a block from Siesta Key Village. Enjoy the convenience of walking to bars and restaurants, plus two parking spots if you prefer to drive. Relax by the community heated pool or take an 8-minute stroll to the award-winning beach. Explore the area using the free trolley, or venture to downtown Sarasota. This dog-friendly condo offers Wi-Fi, a smart TV, in-unit laundry, and essential home and beach gear.

4.97 out of 5 average rating, 326 reviews

Condo in Siesta Key

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!

4.93 out of 5 average rating, 92 reviews

Apartment in Sarasota

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach

Step into your SUMMER Holiday with a Beach Vacation! 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

4.88 out of 5 average rating, 17 reviews

Apartment in Sarasota

Steps to Lido Beach, kayaking, paddle boarding.

EXCITING, newly renovated ground floor unit! Beautiful NEW furniture & finishes. Brand new kitchen & bathroom! Relax & unwind at this unique and tranquil getaway, nestled among the trees & just a short walk to the stunning white sand beaches of LIDO BEACH! Brand new deck off the master for evening cocktails & dinner. Cute patio off the dining area & a screened in lanai for morning coffee. We have a private pool for the complex!

4.94 out of 5 average rating, 111 reviews

Condo in Siesta Key

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.