Holiday rentals with a pool in Lido Key

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

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!

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.

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

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.

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

RARE Sept SALE! OPEN! Sarasota #1 Lux 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!

Gillespie On The Park, Walk to Downtown

Contemporary Studio apartment with balcony above garage. Studio is half block from Gillespie Park with its public walking/jogging/biking paths, tennis courts, basketball court, and retention pond. Within walking distance to downtown and Rosemary District: restaurants, shops, movie theaters, cultural events, Whole Food Market, Starbucks etc.