House vacation rentals in Osprey

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Top-rated house rentals in Osprey

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Sarasota

4.9 out of 5 average rating, 144 reviews

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

Oct. 28 – Nov. 4

$157 CAD per night

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 244 reviews

Lovely guest house

Come get away from everyday life & enjoy this cozy studio located in the heart of Sarasota. This studio is a breath of fresh air- you’ll feel calm and at peace. Sparkling clean & spacious with queen-sized, comfortable bed, a full bathroom and kitchenette. A great location to have the city life, but also quiet enough to relax. Whether you’re here for business or pleasure, this cozy studio is sure to be a highlight.The studio is separate 100 feet from the main house, and It has a private entrance

Aug. 18 – 25

$147 CAD per night

Guest favourite

Home in Sarasota

4.92 out of 5 average rating, 122 reviews

Renovated Cozy Cottage "The Nest" Close to SIESTA

"The Nest" at Snowbird Cottages is a classic coastal farmhouse nestled in an historic Sarasota neighborhood less than 10 minutes to the white sugar sand of World Famous Siesta Key beach! Only a 10 minute drive to St. Armands Circle & Lido Key beach, & the famous Ringling Museum. This cozy cottage is full of charm and amenities alike. Crisp, clean, and freshly renovated for your total comfort, enjoy TWO screened porches, a private fenced yard, comfy beds, free in-house laundry, and fast wi-fi.

Oct. 27 – Nov. 3

$294 CAD per night

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 128 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Sep. 2 – 9

$245 CAD per night

Guest favourite

Home in Sarasota

4.94 out of 5 average rating, 296 reviews

☀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 heated pool and new luxurious outdoor furniture in your fenced in backyard where you can bask in the sun swimming and grilling. - Beautifully remodeled 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.

Aug. 2 – 9

$396 CAD per night

Guest favourite

Home in Venice

4.93 out of 5 average rating, 107 reviews

A Dream Come True

Located in a desirable community of Venice Garden in a quiet neighborhood where you can't tell if it is a weekend or a weekday. The kitchen is fully equipped, beds are amazingly comfortable, the reclining couch and loveseat are great for relaxing. Everything you need for the beach is included in the rental. The private fenced in backyard allows you monitor your pet while enjoying a cup of coffee. Enjoy a guest Netflix account and high-speed internet from XFINITY all included in the rental.

Jun. 1 – 8

$224 CAD per night

Guest favourite

Home in Sarasota

4.99 out of 5 average rating, 201 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

Apr. 25 – May 2

$192 CAD per night

Guest favourite

Home in Venice

4.89 out of 5 average rating, 161 reviews

Venice Pool Villa with Bikes Kayaks Great Beaches!

Relaxing pool home with 2 bedrooms, 1 king bed, 1 queen bed, 1 sofa double bed and one single foldout bed. 2 bathroom pool home just a 8 minute ride away from Manasota beach. Venice beach and caspersons beaches close by too. A great selection of restaurants and plenty of shopping and convenient grocery stores just 5 minutes away!. Also close to bike trails with two FREE bikes at the house and FREE kayaks too. My home is great for everyone! Pets welcome with pet fee, large fenced yard!

Sep. 21 – 28

$267 CAD per night

Guest favourite

Home in Sarasota

4.91 out of 5 average rating, 209 reviews

Cozy Getaway Home in Sarasota Near Beaches & More!

Escape to our peaceful 2-bed, 2-bath 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.

Jul. 8 – 15

$236 CAD per night

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 111 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.

Jul. 14 – 21

$207 CAD per night

Guest favourite

Home in Sarasota

4.87 out of 5 average rating, 204 reviews

The Pineapple Suite.Teal tropical home in Sarasota

This is a perfect space for a vacations, snowbirds, visiting professionals (desk and work station within home), or families looking for a home located in the center of Sarasota, Florida. Access everything you need in just a short ride: beaches, University Mall/UTC, hospitals, interstate, gyms, downtown, yoga, local hangouts, and really good food! [*Important note: For all communication, please use the Airbnb App. It is the fastest, most direct and effective way to reach us!]

Oct. 25 – Nov. 1

$170 CAD per night

Guest favourite

Home in Venice

4.91 out of 5 average rating, 115 reviews

Near historical downtown Venice and Venice beach

Two bedroom, 2 bath updated home in a quiet neighborhood, near Venice Beach. Privacy fence surrounds the backyard, palm trees line the front yard. Enjoy a screened in pool with a cup of coffee, relaxing on the patio, while, watching the squirrels play, blue jays and cardinals fly around the large Mango tree, and Magnolia tree, or end your busy day with a night swim under the stars with the outdoor night lights on. Either way, its a relaxing way of life near Venice beach!

Sep. 12 – 19

$330 CAD per night