Holiday rentals in Kensington Park

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

YC Tropical stay. 100% Private stay & Conford.

Welcome to your brand-new, modern-concept guest suite, available since July 2025! This thoughtfully designed space offers complete privacy and comfort, featuring: ✅ Private entrance ✅ Secluded patio ✅ Two dedicated parking spaces ✅ No shared areas – enjoy your own kitchenette, bathroom, and bedroom Perfect for solo travelers, couples, or business guests looking for a peaceful and stylish stay. Location: 3.8 miles from Sarasota Downtown 7.9 miles from Lido Beach Less than 5 miles from UTC Mall

Costal Breeze Cottage. Pet friendly. King size bed

Escape to this cozy cottage, perfect for a relaxing getaway in sunny Sarasota. Located in a peaceful neighborhood, this open concept home offers partially fenced private yard that backs to tranquil urban nature area - your own serene retreat. Whether you’re visiting for a weekend or an extended stay, this charming spot offers comfort, convenient location to local beaches, shopping, restaurants, downtown, airport, and a touch of nature. Book your stay today and experience what Sarasota offers.

1920s Cottage in a Private Tropical Wooded Setting

Your perfect Sarasota getaway! This lovely little cottage is very private & isolated but just minutes from downtown. Modern conveniences & comfort nestled in a charming and cozy period cottage. You will make yourself at home in this tranquil, cozy, and quaint 1920's Old Florida Guest House. Nestled under a canopy of ivy-covered oaks, pines and the tallest of palms - where the flowers are always in bloom! This captivating cottage is your woodsy home base for all your Sarasota adventures!

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

MG Tropical Stay. Fully private, no shared spaces

Welcome to your modern Sarasota Guest Suite – Adults Only, Private & Peaceful 🌞 Remodeled on January 26, 2026, this private suite offers a separate entrance and parking for two cars. Enjoy a cozy queen bed, full bathroom, and a kitchenette with microwave, mini‑fridge, coffee maker, and more. Relax on your private patio with a solar shower. Stay cool with a quiet mini‑split A/C. We provide beach essentials: umbrella, chairs, cooler, and towels—perfect for your Sarasota beach days 🌴

Tropical vibes🏝: 1-bedroom place with a hot tub 🏝☀️

Private entrance and outdoor area were you can enjoy the sun while you are in the hot tub!!Free parking space for 2 cars .Very FRIENDLY neighborhood!!! You will be close to everything when you stay at this centrally-located place, 0.6 miles from Ed Smith Stadium, 4.1 miles from UTC mall, 8 miles from Florida number one beach “SIESTA KEY”. Also there are few gas stations, restaurants, nail salons, grocery stores and Public transportation within a 0.8 mile radius.

Private Jacuzzi & Mini Golf Near Beaches

Welcome to our Sarasota retreat, a comfortable and private space perfect for a relaxing getaway. Enjoy a spacious, fully fenced backyard featuring a jacuzzi, mini golf, a fire pit, and plenty of room to unwind. Located about 20 minutes from Sarasota’s beautiful beaches and close to UTC, downtown Sarasota, shopping, restaurants, and entertainment. Clean, cozy, and family-friendly, our home is the perfect place to relax, explore, and create lasting memories.

Private Guest Suite with Kitchenette

Private and spacious suite with kitchenette close to the Airport, UTC and Downtown. This roomy mother in law suite is located on a residential road close to everything. Very clean and has all the amenities you need. Kitchenette with several appliances, complimentary coffee. Large bedroom has a comfortable queen size bed, living room has a futon that can sleep 1 person or 2 kids. Large TV with Roku and Netflix, plus fast WiFi. Parking in driveway.

The Seapearl - 1/1 Guest Suite

Welcome to The Seapearl! Relax in this peaceful 1 bed / 1 bath guest suite, ideally located just 10 minutes from UTC, I-75, and SRQ Airport, and only 20 minutes from Lido Key and Siesta Key beaches. The suite includes a sleeper sofa for up to 2 additional guests and a fully enclosed private side yard—perfect for those traveling with pets! Whether you're here for business or a beach escape, The Seapearl offers a cozy, convenient retreat.

Luxury Pool Family Paradise-Siesta Beach Beach

Discover your exquisite home away from home! This beautifully renovated pool home offers ample space and natural light, ensuring a luxurious experience from the moment you step inside. Nestled on a serene street, it provides easy access to Sarasota's top attractions. With proximity to Siesta Key Beach, downtown, and the renowned Fresh Fish Waltz Market, you'll have an unforgettable stay.

Classy & Modern, Minutes to Everything in the City

Surround yourself with style in this standout space with lots of trees and the sound of birds. Everything you need for a peaceful well needed rest and more. Close to SRQ Airport, downtown & UTC. 20-30 mins away from Siesta Key and Lido Beach. At walking distance from restaurants, a wholesale Farm Market and Walmart Supercenter. Gas stations, gyms and laundromats close by.