Vacation rentals with a patio in Osprey

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Top-rated patio rentals in Osprey

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Guest favorite

Home in Osprey

4.96 out of 5 average rating, 23 reviews

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

Jun 25 – Jul 2

G$57,909 GYD per night

Guest favorite

Guest suite in Sarasota

4.98 out of 5 average rating, 106 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Jan 10 – 17

G$29,423 GYD per night

Guest favorite

Home in Osprey

4.97 out of 5 average rating, 33 reviews

Sarasota vacation Home!

We have a beautiful new home available for you and your family which is perfectly located in between siesta key Beach and Nokomis Beach a highly desired area. The house is conveniently located near costco, Walmart publix and a variety of restaurants all within 5 minutes while also being within 15 minutes from the Sarasota boardwalk/downtown area. Also located within 2.5 miles is a boat launch. The interior of the home has brand new furniture and a comforting vacation theme with modern style.

Sep 6 – 13

G$40,646 GYD per night

Guest favorite

Condo in Sarasota

4.98 out of 5 average rating, 60 reviews

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

Nov 11 – 18

G$35,113 GYD per night

Guest favorite

Guest suite in Sarasota

4.93 out of 5 average rating, 115 reviews

Sweet Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

Sep 14 – 21

G$23,095 GYD per night

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 168 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

Sep 3 – 10

G$21,204 GYD per night

Guest favorite

Home in Nokomis

4.95 out of 5 average rating, 19 reviews

Blue Sky Retreat

LOCATION, LOCATION! 3.5 miles from Nokomis beach! LARGE house on a private, fully fenced backyard on a one acre lot with CAGED and HEATED POOL, play house, trampoline, lounge chairs and plenty of area to relax and to play. Peaceful and quiet place with country feeling but centrally located and close to several marinas, boats rentals, shopping, restaurants, arboretum, state parks, Venice downtown, Sarasota downtown, Siesta Key Beach, Venice dog beach, and more...

May 27 – Jun 3

G$45,141 GYD per night

Guest favorite

Home in Sarasota

5.0 out of 5 average rating, 6 reviews

Cozy Heaven Studio III

Enjoy our studio (Attached to the main house) with private entrace. Queen size bed, full bathroom, and small kitchen. Our main house and family are on site. It has a private entrance, One parking spot and no more than 2 people at anytime. Private Patio with Bbq, Beach gear, Tv, Full Kitchen, everything you need to have a great time 🤩 Distance to Siesta Key 18 minutes driving (8 miles), Lido Key 23 minutes driving (10 miles), and I-75 1.5 miles.

Nov 17 – 24

G$15,244 GYD per night

Guest favorite

Cottage in Osprey

4.92 out of 5 average rating, 25 reviews

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.

Jul 26 – Aug 2

G$20,837 GYD per night

Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 26 reviews

Beach house #2

Welcome to our central, peaceful and unique house. Has everything you need for your stay in beautiful Sarasota. Beautiful decorated for you to feel like home. Closed to everything, stores, restaurants, gas station and only 3.7 miles from the most beautiful beach in the USA (Siesta Key Beach). Has a fully fenced private backyard. Nice, clean and quiet neighborhood are with direct access to Tamiami Trail (41).

Aug 23 – 30

G$21,312 GYD per night

Guest favorite

Home in Osprey

4.91 out of 5 average rating, 33 reviews

Sand Dollar Cottage - 15m to Siesta / Casey Key

"Sand Dollar Cottage" is a newly renovated and stylish home, centrally located between Siesta Key and Venice Beach and minutes from Legacy Trail. This beautiful and well equipped 800 sq. foot home comes with blazing fast WiFi and additional TVs in each bedroom for maximum convenience as well as an on-site washer and dryer. Guests also have the option to dine out on the patio or relax on the hammock.

Oct 24 – 31

G$34,473 GYD per night

Guest favorite

Home in Osprey

4.92 out of 5 average rating, 38 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.

Sep 4 – 11

G$27,549 GYD per night