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!

Aug 20 – 27

R3,842 ZAR per night

Guest favorite

Vacation home in Nokomis

5.0 out of 5 average rating, 5 reviews

Royal Coachman Resort ~The Owls Nest~

Amazing location & amenities come with this comfortable park model home! Located in the Royal Coachman Resort just 3 miles from Nokomis Beach! This quiet park has mature pines, a kayak launch on Shakett Creek & just 1 mile from The Legacy Bike Trail. Fully furnished, wifi/cable, washer/dryer included. Turn key accommodation includes everything! Resort amenities include pickle ball, pool, library, tennis, kayaking, & much more. High season rent possible Must have positive reviews on Airbnb

Oct 9 – 16

R1,911 ZAR per night

Guest favorite

Guest suite in Sarasota

4.98 out of 5 average rating, 104 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!

Aug 26 – Sep 2

R2,159 ZAR per night

Guest favorite

Guest suite in Sarasota

4.98 out of 5 average rating, 192 reviews

The Sapphire Suite 1Bed/1Bath

Beautifully elegant suite with a relaxing touch. A pleasant mix of Hispanic and Modern decor in a newly renovated living area complete with all necessities such as wifi, an outdoor patio and your own free parking. The suite is located MINUTES away from all of Sarasota's famous hotspots! It is down the street from Jungle Gardens. A 10minute walk to The Ringling Museum. 10minute drive to Downtown, 15 minute drive to both Siesta Key and St. Armand's Circle. It could not be located more ideally!

Jan 21 – 28

R2,297 ZAR per night

Guest favorite

Condo in Sarasota

4.98 out of 5 average rating, 58 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.

Jul 22 – 29

R2,927 ZAR per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 113 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.

Jul 16 – 23

R2,291 ZAR per night

Guest favorite

Cottage in Sarasota

4.94 out of 5 average rating, 138 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 Fresh Market & 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.

Oct 26 – Nov 2

R2,302 ZAR per night

Guest favorite

Camper/RV in Sarasota

4.91 out of 5 average rating, 32 reviews

Sandmari RV/ 8 miles to Siesta Key

Stay in our 2023 RV located 8.9 miles from Siesta Key. The RV sits next to our home. We live in a safe neighborhood. We are closed to I 75, beaches, parks, UTC mall, restaurants, stores, etc. The Rv has one queen bed, dining table that collapses in a twin bed. Nice and comfortable place to stay. Kitchen have microwave, oven, stove, rice maker, coffee maker, toaster. We include the use of the pool, fire pit, and outside areas.

Jul 14 – 21

R1,822 ZAR per night

Guest favorite

Cottage in Osprey

4.96 out of 5 average rating, 23 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 16 – 23

R1,879 ZAR 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 3 – 10

R3,029 ZAR 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 25 – Oct 2

R2,601 ZAR per night

Guest favorite

Guest suite in Sarasota

4.9 out of 5 average rating, 144 reviews

LITTLE HOUSE SUNSET. (Casita Sunset)

After enjoying a beach day or exploring the city attractions, have a relaxing rest in Casita Sunset. It's located in the center of Sarasota about 1.3 mi from ED Smith Stadium, 3.8 from Marina Jack, 5.4 mi from Sarasota-Bradenton Airport, 6.2 mi from UTC Mall, 6.7 mi from Lido Beach, and 9.7 mi from Siesta Beach.

Jun 30 – Jul 7

R1,242 ZAR per night