Holiday rentals in Kensington Park

Updated Ranch Near Beaches/Downtown - Pet Friendly

Updated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat-in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high-speed Wi-Fi. Grab the provided beach chairs, umbrella, and cooler to enjoy Lido or Siesta Key Beaches, both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the fully fenced private backyard. Enjoy several nearby golf courses, or catch Orioles spring training at Ed Smith Stadium

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!

2 bed 2 bedroom house w/ pool

Charming Corner Lot with a Central Location This spacious and beautifully updated home is perfectly situated in the heart of Sarasota. Enjoy the convenience of being just: 10 minutes from vibrant Downtown Sarasota 12 minutes to Sarasota-Bradenton International Airport (SRQ) 20 minutes to the serene shores of Lido Beach 25 minutes to the world-renowned Siesta Key Beach Experience comfortable living with easy access to everything Sarasota has to offer—beaches, shopping, dining,,and more.

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 🌴

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.

The Black Swan | Private Pool + Outdoor Dining

BNB Breeze Presents: The Black Swan! Nestled in a peaceful neighborhood, the property provides a bright, stylish interior and a private screened-in pool area perfect for unwinding in the Florida sunshine. This charming location creates a comfortable setting for relaxation. Your amenity list includes: - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Grill - Outdoor Dining Area - and More!

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.

Blue Home -away

Relax with the whole family at this peaceful place to stay.Near to the areas beautiful beaches Siesta Key, Lido Beach and more, close to new Shopping Center UTC, Close to downtown Sarasota, the bay and more. making it the perfect location to stay very well centered. Minutes from I-75. All new remodeled and clean house with you in mind! To offer a peacefull and tranquil getaway for you!