Vacation rentals with a pool in Downtown, Sarasota

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

Modern coastal downtown home w/saltwater pool

Enjoy a clean experience at this centrally-located home. Located in a family oriented neighborhood, minutes from downtown Sarasota. Get to world class beaches (Lido and Siesta) in under 10-15 mins About this home: 3 bedroom, 2 bathroom 1600 sq ft home on oversized city lot. Comfortably sleeps six Pool details: Saltwater pool, approximately 5.5 feet deep. Heated to 84 in winter, tanning shelf Furniture: Stearns & Foster Handcrafted King sized mattress, American made sofas by Maiden Home

LUX Downtown/Siesta Key heated pool & great yard

Cozy nomadic vibe on the the gulf coast! Meet our Tulum inspired Florida retreat, fully renovated and designed by well sought after interior designer, to make hanging in the sun comfortable and relaxing! Amazing stay for an adult getaway or some fun family time. Don't see your dates available? Message us, sometime we have flexibility! Check out our other bespoke stays at KD Interiors Getaways Nomadic Adobe KD Interiors Getaways Shore House KD Interiors Getaways Nomadic Manor

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.

Saltwater Pool & Hot Tub-Gas Grill-Bikes-Baby Gate

The House - Sleeps 12 people. -Saltwater heated pool -4 person hot tub -Kid’s toys & accessories, including stroller, carseat, highchair, pack and play, etc… -Bikes! -Stocked kitchen -King beds. Location: - 5 minute walk to downtown, 8 minute drive to Lido Key Beach. -Directly next to our “sister house” … book both for huge groups! Hosts -Small family run side-business. We love connecting with visitors! WE OFFER A DISCOUNT FOR PUBLIC SCHOOL TEACHERS! Message us for info!

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool.

Apartment in Sarasota

Take a break and unwind at this peaceful oasis. This Condo is located near Lido Beach, Downtown Sarasota, St. Armand's Circle and SRQ Airport. Come home after a day at the beach, or a walk in Downtown and relax in the big public pool, hot tub, fire pit, barbecue grills, and modern gym. Sarasota had a lot to offer. Sarasota has UTC mall, Marie Shelby Gardens, and Jungle Garden. There are numerous other fun activities to do with your family in Sarasota.

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!