Holiday rentals in Kensington Park

5 out of 5 average rating, 14 reviews

Costal Breeze Cottage. Pet friendly. King size bed

Escape to this cozy and inviting cottage, perfect for a relaxing getaway in sunny Sarasota. Located in a peaceful neighborhood, this open concept home offers 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.

4.99 out of 5 average rating, 128 reviews

Flat in Sarasota

*Recently Updated* Cozy Oasis, centrally located

This cozy yet spacious apartment is very centrally located... Just 5 min from downtown, 10-15 min from Siesta and Lido bch and St Armands Crl, and within walking distance of the historic Amish district. The newly completed Legacy Trail (perfect for walking, biking...) is less than a 5-minute walk away. The space is very private and clean and Ive taken extra measures to ensure your absolute peace and comfort. It includes all the amenities you'll need to make your getaway a memorable one.

4.94 out of 5 average rating, 160 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated 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 WIFI. Grab the beach chairs and umbrella to enjoy Lido Key or Siesta Key Beaches both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses near-by or catch Orioles spring training at Ed Smith stadium within walking distance.

4.93 out of 5 average rating, 228 reviews

Guest suite in Sarasota

MG Tropical Stay.With private entrance and patio.

Welcome to your modern Guest Suite in Sarasota – Adults Only, Private & Peaceful 🌞 Enjoy your own private space—no shared areas—with a separate entrance and parking for two cars. The suite includes: A cozy queen bed A full bathroom A well-equipped kitchenette with a microwave, small refrigerator, coffee maker, and 2-burner cooktop A secluded outdoor patio with a solar shower, ideal for rinsing off after a beach day A mini-split A/C unit to keep you cool during Florida’s sunny days

4.94 out of 5 average rating, 101 reviews

Luxury Pool Family Oasis-Siesta Beach/DT-3BR/2BA

Embrace the height of comfort and convenience at your home away from home! Step into this meticulously renovated pool home, where spaciousness and brightness create an atmosphere of sheer luxury. Tucked away on a serene street, it offers a serene setting while keeping you close to Sarasota's prime attractions. Experience the allure of Siesta Key Beach, the vibrant downtown ambiance, and the renowned Fresh Fish Waltz Market—all just moments away. Plus, enjoy easy access to I-75.

4.91 out of 5 average rating, 260 reviews

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.

Place to stay in Sarasota

4.89 out of 5 average rating, 9 reviews

Low Cleaning fee - Luxe, Cozy, Upscale & private

Welcome to Your Cozy & Luxurious Urban Getaway! Experience the perfect blend of comfort, style, and location. This modern & private space offers a warm and sophisticated atmosphere, ideal for anyone looking to relax without leaving the heart of the city. Enjoy thoughtfully designed spaces, elegant decor, and all the amenities you need for an unforgettable stay. Whether it’s a weekend escape, a business trip, or a longer vacation, this is your perfect home away from home.

4.95 out of 5 average rating, 66 reviews

Guest house in Sarasota

The Cute and Cozy Bungalow

This clean and peaceful bungalow is located in the back part of a private property with a seperate private washer and dryer as well as a large shared yard. It provides a peaceful, cozy spot for your time away in Sarasota! The home is in a 10-20 min radiance of the #1 beach in Florida (Siesta Key beach), St. Armands Circle, Downtown Sarasota, Benderson Rowing Park, UTC shopping mall, and riding trails. Our hope is it offers the perfect getaway for your stay in Sarasota.

4.93 out of 5 average rating, 193 reviews

Sea-esta Cottage- Cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand-new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

4.99 out of 5 average rating, 104 reviews

Bright & Peaceful 1920s Cottage: Close to UTC!

Experience the timeless charm of this 1920s beautifully preserved cottage – where original details meet modern comforts. A bright & peaceful property nestled on half an acre with plenty of space to spread out, natural light that pours into every room, & a private fenced in yard - it's an ideal spot to entertain AND unwind. Whether you are headed to the beach, Benderson Park, Downtown or UTC mall, this neighborhood is central to anything you'll need!

4.98 out of 5 average rating, 155 reviews

Secluded Cottage | Hot Tub | Walk to Benderson/UTC

Welcome to The Crew House! A brand new, stylish, cozy cottage that is walking distance to all that the Nathan Benderson Park and University Town Center areas have to offer! The property is on over a 2 acre parcel so there's plenty of room to spread out. At our cottage you will find a comfortable bed, stylish furniture, high-end finishes, a large island, screened-in outdoor dining table, and a great outdoor space with a private hot tub.