Holiday rentals in Kensington Park

The Animal House

Relax with the whole family at this peaceful place to stay. Fun animal themed, totally remodeled upstairs apartment with one bedroom and kitchen. Private entrance and on driveway parking. Private screened lanai upstairs with outdoor dining and room for family games or entertaining. Access to the pool and lanai (newly renovated), fire pit, treehouse, swing and your own gas grill for guest use. Spacious back yard on a cul-de-sac. Close to shopping, dining, beaches, the airport and the interstate.

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!

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 🌴

Cozy Getaway Home in Sarasota Near Beaches & More!

Escape to our peaceful home in Sarasota. Conveniently situated near our famous beaches, UTC, Benderson Park, downtown, and only within a mile of grocery stores and other shops. Enjoy outdoor moments on the patio and spacious yard. Modern amenities include high-speed internet, smart TVs, and a well-equipped updated kitchen and workspace. Washer/dryer on-site as well. Your gateway to relaxation and Sarasota's charm awaits! Please reach out if you have any further questions.

Sunshine House- Sarasota Pool Retreat

Welcome to the Sunshine House a sunny Sarasota retreat! This charming 3-bedroom, 2-bathroom home features a salt water heated pool and is just 20 minutes from the stunning Lido and Siesta Key Beaches. Perfect for families or groups, our home offers a spacious living area, fully equipped kitchen, comfortable bedrooms and an office setup. Relax by the pool, enjoy nearby dining and shopping, or explore the beautiful beaches. Your perfect getaway awaits!

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.

Exclusive pool villa near Siesta Key 3BR/2BA

Prepare to be enchanted by your new sanctuary! Immerse yourself in luxury at this spacious and bright pool home, recently renovated to perfection. Located on a peaceful street, it strikes the perfect balance between tranquility and convenience, with easy access to Sarasota's finest attractions. Unwind at Siesta Key Beach, indulge in downtown's culinary delights and shopping, and explore the famous Fresh Fish Waltz Market—all just minutes away!

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.

"Serenity Now" 3BR House in the Heart of Sarasota

Welcome to our beautiful modern house in Central Sarasota. Find your inner peace and ultimate relaxation in this spacious and thoughtfully stocked home away from home. Located in a quiet family neighbourhood, yet very centrally positioned to all the amenities Sarasota has to offer, including the collection of spectacular white-sand beaches; diverse dining, enriching arts and culture, shopping and natural Florida fun.