
House holiday rentals in Osprey
Find and book unique houses on Airbnb
Top-rated house rentals in Osprey
Guests agree: these houses are highly rated for location, cleanliness and more.

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.

3 bedroom Heated salt water pool close to Siesta
Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

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!

Spectacular Sunsets! 15 min Siesta Key!
This villa is spacious and bright with lots of windows. The interior has just been updated. Tropical decor makes you feel like your’e at the beach. Huge flat screen TV. Tile flooring in the living areas and laminate in the bedrooms. Screened lanai overlooks palm tree and mature landscaping. Wireless fast speed internet included. It has everything you need for a short visit or extended stay. Fully equipped kitchen. Washer and Dryer. Beach chairs and towels. One car garage and driveway space.

7 Min to the BEACH 2 King Beds Fenced yard PETS OK
Sandy Flamingo Vacations is offering this spacious and fully renovated home in South Venice, located just south of Sarasota. 2 bedrooms, 2 baths and a bonus room/game room. It is ideal for both work and leisure travel, offering a serene retreat to enjoy activities such as sunny beaches, fishing, boating and exploring. The backyard is fully fenced, featuring a BBQ grill and patio table for outdoor dining. The kitchen is fully stocked, making it suitable for long stays and family cooking.

Beach Retreat•Renovated Pool Patio•Near Siesta Key
Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

Comfortable + Functional Private Studio Apartment
This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and well equipped kitchenette, you will be lacking nothing here. This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

2 BR House 1.6 miles from Siesta Key Beach
Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

Cute Little Getaway
Close to the beach and walking distance to 5 restaurants, including one on the water. Our place is less than 2 miles from Nokomis Beach! We have you covered on beach equipment, wagon, chairs, towels and umbrella. The backyard boasts a relaxing, beautiful escape with resort style touches. We have a gas grill to cook your catch, a high powered outdoor fan, and comfy seating in the shade. The house is freshly modernized, open and airy. You will enjoy an outfitted kitchen.

1 Bed 1 bath 7 mins to the beach
This charming 1 bedroom 1 bath space has a calming coastal vibe with dedicated driveway parking, front porch, and fenced backyard. This unit is newly renovated and furnished, and is part of a duplex with a large shared backyard. It is within walking/biking distance or a short drive to grocery stores and restaurants, and 7 mins to Siesta Key - FL's #1 beach! Longboat Key, St. Armands, Turtle Beach, and Downtown are all a short drive away!

PERFECT FLORIDA GETAWAY !
Only 5min from Venice historic downtown and 10min from Venice beach ! Very well located, our vacation rental home offers everything you need to enjoy your stay. The apartment is a 1bedroom/1bathroom for 2 people. Totally separated from the main house. Restaurants and shops in beautiful historic Venice downtown. Close to many beaches and the Legacy Trail. About 7 miles from Siesta Key, America's #1 beach !

Magical Secluded Retreat
Light-filled mid-century gem, newly renovated with cathedral ceilings. A lush canopy of tropical plants and trees offers privacy and calm unusual for its central location in Sarasota's historic neighborhood on the Bay. Relax inside and out, and lose yourself in birdsong, gently swaying bamboo and beautiful nature. Just 10 minutes to world-renowned beaches and even closer to dining, shopping and museums.
Popular amenities for house rentals in Osprey
House rentals with a pool

Beachfront Getaway in Siesta Key

Spacious 2 Bedroom Home | Near Beach | Heated Pool

New remodel- 150 Yds to Beach and Restaurants!

Resort-Style Vacation Villa

1 House 1400sq. ft. 12 min from Siesta Key!

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Perfect Getaway 3bd/2bth Private Heated Pool

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough
Weekly house rentals

Great location! Updated & loaded with all you need

Palm Patio Hideaway

Big backyard hangout, firepit, large primary suite

Beach house

Family-Friendly Retreat Near Siesta Key+Beach Gear

Pet-Friendly Modern Retreat Near Siesta Key

Siesta Key Fully-Renovated Unit 5 min to the beach

Charming Osprey Home
Private house rentals

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Ashota - The Jellyfish

Coastal Retreat near Siesta Key Beach and Downtown

Costal Breeze Cottage. Pet friendly. King size bed

5 mins to the beach! Come relax!

Shoreline Coastal Escape

Coastal Haven 3BR/2BA Beach Home

Sarasota Serenity - Minutes to Beach
When is the best time to visit Osprey?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $247 SGD | $278 SGD | $335 SGD | $260 SGD | $220 SGD | $220 SGD | $189 SGD | $221 SGD | $227 SGD | $200 SGD | $186 SGD | $256 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about house rentals in Osprey

Total holiday rentals
Explore 50 holiday rentals in Osprey

Nightly prices starting at
Osprey holiday rentals start at $101 SGD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Osprey holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Osprey rentals

4.7 Average rating
Osprey stays receive an average rating of 4.7 out of 5 from guests
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- Family-friendly rentals Osprey
- Rentals with a patio Osprey
- Pet-friendly rentals Osprey
- Rentals with pools Osprey
- Rentals with a washing machine and dryer Osprey
- Fitness-friendly rentals Osprey
- Rentals with a firepit Osprey
- Rentals with a hot tub Osprey
- Rentals with outdoor seating Osprey
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