Vacation rentals in Osprey

4.91 out of 5 average rating, 200 reviews

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

Home in Sarasota

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

Superhost

A serene lake mirrors the surrounding landscape, showcasing greenery and trees along the shoreline. The cloudy sky is reflected in the still water, creating a calming ambiance. The scene emphasizes the natural beauty and tranquility of the property.

Home in Nokomis

4.73 out of 5 average rating, 342 reviews

The Ibis Cottage

Freshly renovated, The Ibis Cottage is a cozy studio on a beautiful property overlooking a small lake. It is a 5 minute drive to Nokomis Beach, Siesta Beach and Venice Beach are within easy reach, and a block away to the Legacy Trail bike path (Sarasota to Venice). Enjoy seeing a variety of birds on the property including the ibis, heron, and snowy egret. The cottage is conveniently located between Sarasota and Venice. The perfect location for enjoying the Gulf coast and outstanding beaches.

Home in Indian Beach-Sapphire Shores

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

4.97 out of 5 average rating, 156 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

4.97 out of 5 average rating, 283 reviews

A spacious bedroom features a king-size bed adorned with a blue and white textured coverlet. Soft natural light filters through the window, illuminating the room, which includes a nightstand, dresser, and a comfortable bench at the foot of the bed.

Guesthouse in Sarasota

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

4.93 out of 5 average rating, 371 reviews

A bright and airy indoor space features a coastal-themed rug with a starfish design. Light-colored furniture and a wooden table provide a casual dining area, while large windows allow natural light to fill the room and offer views of the backyard.

Home in Pelican Cove

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the pool and patio (renovated in July 2025) and comfy outdoor furniture in your fenced in backyard where you can bask in the sun. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

4.97 out of 5 average rating, 66 reviews

An enclosed sitting area features a comfortable daybed adorned with colorful throw pillows against light wooden paneling. A small blue table accompanies the seating, with large windows allowing natural light to illuminate the space while offering views of the surrounding greenery.

Cottage in Osprey

Mattie’s Cottage by the Bay

Enjoy this 1913 Florida vernacular cottage! Carefully restored, thoughtfully updated house on a quiet, tree-canopied street in historic Osprey, one of Sarasota County’s oldest settlements. Enclosed front porch, screened back porch, and tin roof. Walk to the bayfront, restaurants, shopping, library, parks, and historic sites. A short drive takes you to famous Gulf beaches and all Sarasota and Venice have to offer. Hurricane Milton: Yes, we are cleaned up and have power and internet!

A modern living space is displayed, featuring a large gray sectional sofa and a circular wooden coffee table. The sleek kitchen with dark cabinetry is in view, complemented by pendant lighting and a spacious countertop. Natural light enters through the windows, enhancing the contemporary design.

4.93 out of 5 average rating, 84 reviews

Private house with loft

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green. Centrally located between Siesta Key beach and Nokomis beach. Hot tub is available upon request in off season months, April-October. There will be an additional $30 fee in off season months.

Cottage in Bellevue Terrace

A private pool is surrounded by a paved area, featuring two lounge chairs positioned near the water. Green foliage adds a natural touch, while a white fence encloses the space, creating a secluded atmosphere. The clear blue water reflects the sky, inviting relaxation.

4.92 out of 5 average rating, 131 reviews

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.

4.93 out of 5 average rating, 195 reviews

The front exterior of the home features a light grey facade with stone accents. Two comfortable chairs are positioned on the covered porch, inviting relaxation. A brick driveway with ample space leads up to the entrance, surrounded by landscaped areas and a peaceful neighborhood view.

Home in Sarasota

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.

The property is surrounded by lush greenery, featuring a spacious driveway leading to a single-story home. Tall palm trees and various plants are visible in the yard, creating a tropical ambiance. The structure is situated in a serene neighborhood, showcasing nature's beauty.

4.96 out of 5 average rating, 49 reviews

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

4.98 out of 5 average rating, 164 reviews

A row of brightly colored Adirondack chairs is positioned on the sandy beach, facing the tranquil ocean. The hues include yellow, orange, green, blue, pink, and purple. A clear blue sky with soft clouds complements the serene shoreline.

Cottage in Nokomis

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

Superhost

A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. A colorful piece of wall art draws attention, while two pendant lights cast a warm glow. A small white table holds a yellow lamp, and a potted plant adds a touch of greenery.

Bungalow in Osprey

4.78 out of 5 average rating, 360 reviews

Osprey,Buttonwood Cottage.Hot tub -patio.Sublime !

Floridian Tiny Cottage! Buttonwood Cottage is wonderfully located central to the downtowns and beaches of Sarasota and Venice with a private patio space and hot tub. 15 minutes away for the number 1 beach in USA "Siesta Key" . You'll feel that you stepped back in time upon arrival to our charming homestead. I follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance. Here are a few highlights:

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Popular amenities for Osprey vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Osprey

The exterior of a single-story coastal home is presented, featuring a light-colored façade with stone accents. A curved driveway leads to a garage, and lush landscaping complements the structure, providing a welcoming atmosphere. Blue accents on the front door enhance the inviting entryway.

4.98 out of 5 average rating, 50 reviews

Sarasota vacation Home!

4.98 out of 5 average rating, 44 reviews

A modern kitchen features white cabinetry and a large wooden island with blue accents. Shelves display green glassware and plants, while stainless steel appliances, including a microwave and dishwasher, are neatly arranged. Art adorns the wall, adding a coastal touch to the space.

Guesthouse in Nokomis

Serenity near the Coast

4.89 out of 5 average rating, 27 reviews

A cozy living area is presented with a leather sectional sofa arranged around a round table. Light-colored walls are complemented by a feature wall of rustic wood panels. A flat-screen television is mounted for entertainment, with a view of the dining area and kitchen beyond.

Home in Nokomis

Great location!Updated & loaded with all you need

The image captures an ocean scene as waves crest against the shoreline, showcasing dynamic white foam. The sky is filled with a gradient of orange and gray hues, signaling sunset, with the sun's rays peeking above the horizon, creating a serene and tranquil atmosphere.

5 out of 5 average rating, 14 reviews

5 mins to the beach! Come relax!

5 out of 5 average rating, 27 reviews

A welcoming exterior of a single-story home is showcased, featuring a covered entry with an arched design. Lush greenery flanks the pathway leading to the front door. A well-maintained lawn invites a sense of serenity, and a bright sky enhances the overall appeal.

Home in Sarasota

Sarasota Tropical Place in the Heart of the Gulf!

5 out of 5 average rating, 12 reviews

A spacious waterfront home is surrounded by green landscaping, palm trees, and open blue skies. A large heated pool is visible in the backyard, adjacent to a well-maintained deck. Comfortable seating is positioned on the sandy area by the water, providing a relaxing atmosphere.

Villa in Osprey

Paradise with a pool, pier and private beach area

Superhost

Camper/RV in Osprey

4.5 out of 5 average rating, 4 reviews

Thyme on Green

A heated private pool is surrounded by a screened enclosure, providing a serene outdoor space. Lush tropical landscaping and trees create a tranquil backdrop, enhancing the sense of privacy. The pool features a gentle curve and a built-in entry handrail for ease of access.