Vacation rentals with a patio in Osprey

4.96 out of 5 average rating, 116 reviews

The modern exterior of the home features clean, white walls accented by a textured stone wall. Black light fixtures are strategically placed, contributing to the contemporary design. Lush greenery surrounds the property, enhancing the inviting atmosphere under a clear blue sky.

Home in South Venice

Mins to Beach-Coastal +Modern+Spacious w/3 Masters

Find "Serenity by the Sea" at this modern home with 3 master bedrooms just minutes from Nokomis, Caspersen and Venice beaches. Enjoy crisp percale bedding and comfortable beds plus an ensuite bathroom in each bedroom. Perfect for relaxing after a day exploring Venice and the unique Gulf coast areas. Minutes from a local Park and Nature Center full of nature trails, playground and local flora and fauna. Nothing says "Welcome to Vacation" like a salty breeze and sunshine! MANAGED BY RELAX STAYS

4.98 out of 5 average rating, 55 reviews

A spacious living area features a light-colored sectional sofa and a round coffee table in the center. Natural light pours in through large windows, illuminating the room's wood accents and open layout. A dining area with a wooden table and chairs is visible in the background.

Home in Osprey

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!

4.99 out of 5 average rating, 92 reviews

A screened-in pool area is presented, featuring a clear blue pool surrounded by stone pavers. Lush greenery and water views are visible through the screen, enhancing the sense of tranquility and connection with nature.

Cottage in Nokomis

New Pool Tropical Waterfront Dock & Optional Boat

We have electric power! Home stayed dry during hurricane Milton. Clean and ready! Located on a highly desirable street, the house is perched high above Curry Creek offering spectacular water views from every room. The property includes a boat ramp to avoid the public launch. Three kayaks (two tandems and one single). Two miles from Nokomis Beach and only half a mile from The Legacy Bike Trail. You can do so many fun things, or just have a drink on the dock and watch the manatees. Pet Friendly

4.95 out of 5 average rating, 108 reviews

A bright living space is highlighted by a cozy sectional sofa and a decorative trunk. A wooden dining table with chairs is positioned near a doorway featuring a decorative glass design. The kitchen area, equipped with stainless steel appliances, is visible in the background.

Villa in Nokomis

Apr SALE! New modern 1 min to Beach, Yard, Pets OK

Our unique villas sit just 1/2 mile from one of Florida's most pristine beaches. Biking, boating, kayaking, museums, as well as great dining/shopping are easily accessible. The villas also have an attached yard/field perfect for pets to run and exercise. Max pet weight 40 lb total. The local beach has only one access point for over 7 miles of private beach, Casey Key is a secret gem! As superhosts we love creating great memories, please read our reviews! Two adults, two kids maximum capacity:)

4.97 out of 5 average rating, 30 reviews

A single-story home with a gray exterior features a bright yellow front door. The property showcases a well-maintained lawn and a spacious driveway. Outdoor seating is arranged on a patio area, surrounded by greenery and trees, creating an inviting space for relaxation.

Home in Osprey

Sand Dollar Retreat

Escape to our relaxing 2-bedroom home in Osprey, Florida, just minutes from the stunning beaches of the Gulf of Mexico, pristine golf courses and MLB spring training. This peaceful retreat sleeps up to 7 adults and offers a perfect blend of comfort & convenience. The master bedroom features a queen bed and the second bedroom has a bunkbed sleep system with a queen mattress on bottom and twin mattress elevated above. There is also an office with a daybed & trundle for additional sleeping space.

5 out of 5 average rating, 16 reviews

Home in Nokomis

Casey Key, Gulf Coast Gem, 4 Bedroom Private Pool

Bright and Sunny Gulf Coast Getaway, Welcome to Gulf Dream, property offers 4 bedrooms, 2 full bath rooms a washer and dryer as well as plenty of room to enjoy the screened in Lanai and in ground pool, located in a quiet serene Casey Key neighborhood, Ocean breezes, and lots of sunshine, and various fruit trees this property is located just minutes from Venice Beach ( Shark Tooth Beach) 9 minutes, Nokomis Beach, (Just 8 minutes) and Siesta Key Beach (12 minutes away) #1 Beach in the USA

4.99 out of 5 average rating, 124 reviews

A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.

Home in South Sarasota

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

4.98 out of 5 average rating, 121 reviews

A spacious living area is highlighted by a light-colored sectional sofa adorned with colorful pillows. A large coffee table is positioned in front of the sofa, and a dining table with six chairs is visible in the background. A fan hangs from the ceiling, and natural light enters through nearby windows.

Condo in Vamo

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.

5 out of 5 average rating, 19 reviews

Guesthouse in Osprey

Private Coastal Getaway - Your Home Away from Home

Enjoy privacy, luxury, and comfort in this 2-bed, 1-bath coastal guesthouse, perfect for business trips or extended stays. Accommodating up to 4 guests, it features a leather Reclining Sectional, two Queen Beds with storage, and a Private Outdoor Space with seating and a Blackstone grill. Located in Osprey, FL, you're ideally situated between Siesta Key, Nokomis, and Venice beaches—just minutes from sand and sun! Set down your bags and grab complimentary beach chairs, umbrella, and cooler!

4.96 out of 5 average rating, 83 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!

4.89 out of 5 average rating, 95 reviews

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.

Home in Osprey

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.

4.93 out of 5 average rating, 14 reviews

Home in Vamo

Posh Siesta Key Beach Getway

March Special DISCOUNT message for details Beach home under 11 minutes to Siesta Key beach & attractions : 20 minutes to the airport 15 minutes to UTC Hammock Fire pit Foosball Backyard patio seating Grill Cozy Decor Comfy beds Fully stocked kitchen Fully stocked bathrooms Minutes to shops & restaurants Quite and safe location Escape to this beautiful home in quiet South Sarasota The perfect blend of comfort, location, and charm for your beach tea

Popular amenities for Osprey accommodations with an outdoor patio

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.98 out of 5 average rating, 168 reviews

A spacious living area is adorned with a light blue sofa and a comfortable armchair, complemented by a coffee table and decorative rug. A mounted TV is set against a striking blue accent wall, and natural light filters through sheer curtains, enhancing the coastal ambiance.

Apartment in Siesta Key

Cozy Coastal Getaway 2 min Walk to Beach & Village

Apartment in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 163 reviews

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

Superhost

Apartment in Nokomis

4.87 out of 5 average rating, 31 reviews

Nicely remodeled one bedroom apartment.

4.84 out of 5 average rating, 113 reviews

A spacious sleeping area features a queen-size bed with a light blue patterned bedspread. A cozy armchair is positioned beside the bed, and window treatments allow natural light to brighten the room. Light wood flooring complements the neutral-toned walls.

Apartment in Lido Key

Lido Key FL Studio/Efficiency 5

4.91 out of 5 average rating, 101 reviews

A covered seating area is furnished with comfortable wicker chairs and lounge chairs featuring green cushions. Lush plants and palm trees enhance the outdoor space, while a view of the shared garden can be seen in the background. A book and a sun hat rest on a side table.

Apartment in Sarasota

Minutes to Siesta or DT w/heated pool and Hot Tub

4.93 out of 5 average rating, 217 reviews

A spacious outdoor deck is adorned with comfortable lounge chairs and surrounded by vibrant greenery, including tall palm leaves and flowering plants. Large planters accentuate the area, which is bathed in natural light, creating a serene outdoor retreat.

Apartment in Bradenton

Seahorse Suite Bradenton Hideaway

Superhost

A bright living area features a soft blue sofa paired with textured cushions. A glass coffee table rests on a light rug. Sliding glass doors offer views of a private garden, while light blue curtains complement the neutral decor.

Apartment in Gulf Gate Estates

4.78 out of 5 average rating, 105 reviews

Garden Condo w/ Heated Pool Near Siesta Key | 1BR

Apartment in Saint Armands

4.92 out of 5 average rating, 114 reviews

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach

House rentals with an outdoor patio

5 out of 5 average rating, 15 reviews

A private pool area is showcased within a screened enclosure, featuring clear waters and sun loungers. Colorful umbrellas in red and green provide shade, while tall palm plants are arranged around the space. The adjacent home showcases large windows, offering views of the inviting outdoor area.

Home in Arlington Park

Sarasota's Luxury Oasis

5 out of 5 average rating, 33 reviews

An open living area features cozy seating arranged around a coffee table, with a modern electric fireplace nearby. Sunlight filters through large windows, illuminating the space. The dining area is visible in the background, showcasing a round table with comfortable seating for four.

Home in South Venice

🌺 Stunning 2 Br/2 Ba Pool Home Near Beaches

4.84 out of 5 average rating, 32 reviews

A charming house is situated on a cul-de-sac, featuring a well-maintained exterior and a single-car garage. Lush greenery and palm trees surround the home, contributing to a serene setting. The driveway is spacious, leading to the entryway, which can be seen through the open front porch.

Home in Nokomis

Nirvana In Nokomis

4.97 out of 5 average rating, 37 reviews

A spacious bedroom is illuminated by natural light from sliding glass doors. The area features a large bed with blue accents, a comfortable armchair, and a desk. A muted rug complements the wooden flooring, while plants and decor add a touch of greenery.

Home in Sarasota

Resort-Style Vacation Villa

Home in Gulf Gate Estates

5 out of 5 average rating, 9 reviews

Cottage by the Coast 6 min to Siesta Beach!

4.94 out of 5 average rating, 32 reviews

An aerial view captures a light blue house with a spacious driveway and manicured lawn, surrounded by lush greenery and a serene canal. The home features a charming front porch and is set within a quiet neighborhood, showcasing the tranquil natural landscape.

Home in Port Charlotte

Peaceful waterfront home

5 out of 5 average rating, 21 reviews

Home in Nokomis

Comfortable Coastal Retreat. 2 Blocks From Beach

4.85 out of 5 average rating, 20 reviews

The living area features a light and airy design with a blue sofa and armchair arranged around a coffee table. A flat-screen TV is mounted on the wall, and natural light filters through shuttered windows, enhancing the cozy atmosphere.

Home in Vamo

Coconut Cottage, pets OK, kayaks and bikes, Vamo

Condo rentals with a patio

A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.

5 out of 5 average rating, 150 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.

4.91 out of 5 average rating, 116 reviews

The Honeymoon Suite on Siesta Key Beach

A detailed map highlights the location of Siesta Key, showcasing nearby points of interest and roadways. The Gulf of Mexico is indicated to the southwest, while the surrounding areas and other keys are marked, providing context for travel and exploration.

4.88 out of 5 average rating, 112 reviews

Bayside Sunrise Cottage on Siesta Key!

4.93 out of 5 average rating, 137 reviews

A stylish living room is presented, featuring a comfortable gray sofa paired with a decorative round coffee table. Brightly colored wallpaper adorned with shell patterns enhances the space, while large windows allow natural light to filter in, complemented by light-colored flooring.

Condo in Bradenton

Minutes to AMI • Walk to Beach & Bay

4.97 out of 5 average rating, 126 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Condo in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

4.97 out of 5 average rating, 141 reviews

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

Condo in Bradenton

KING Bed + Anna Maria Island Beaches + Beach Gear!

4.99 out of 5 average rating, 168 reviews

Condo in Longboat Key

Vitamin Sea Escape: April Availability!

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.