
Vacation rentals in Osprey
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Osprey
Guests agree: these stays are highly rated for location, cleanliness, and more.

Sunshine Cottage
Our Sunshine Cottage is clean, quiet, and all yours! Enjoy the calming views of this beautiful property from your patio. It is located off a main road that takes you to Nokomis Beach in 5 minutes. Ideal for those who enjoy going to the beach, looking for shark teeth and shells. Conveniently located between Sarasota and Venice, it is the perfect place to sightsee, shop and enjoy great local food. Just around the corner from Oscar Scherer State Park and within walking distance of the Legacy Trail.

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!

Luxurious Private Apartment in a House Near Siesta
Large modern construction 950 sq ft 1 bedroom apartment. Beautifully furnished apartment attached to the side of the main house. This upstairs unit has a private entrance with a modern interior & high ceilings. The apartment offers 1 King bed, full kitchen, a bathroom w shower, a washer and dryer, 2 tvs. Nestled on a quiet street with easy access to Siesta Key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key on . Guest must be able to climb one flight of stairs

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!

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.

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.

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!

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA Siesta Key condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity!

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.

The Cottage (In the Country) Cozy, Quiet Retreat
Relax, unwind and unplug at this cozy Old Florida-style country cottage! Here you are away from it all in peaceful bliss... but if you want to go out for dinner, it's an easy drive into town! Located on a beautiful 5 acre plot, this guest home is the perfect spot for your Florida getaway! Just 30 minutes from Siesta Key and 6 minutes from the entrance to Myakka State Park, you can see the best of Florida, both the swamps and the beaches, all in one day!

Staycation Sanctuary
Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!
Popular amenities for Osprey vacation rentals
Other great vacation rentals in Osprey

Nokomis Waterfront Unit Walk to the Beach & Dining

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!

Brand New Apartment by the Beach

Cottage by the Coast 6 min to Siesta Beach!

Water Access Retreat | Kayaks + Hot Tub

Near Beach and Walk to Restaurants. Comfortable

Lux Siesta Key Beach Getway

Beautifully updated home 7 min to Siesta Key Beach
When is the best time to visit Osprey?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,722 ZAR | R2,513 ZAR | R3,221 ZAR | R2,545 ZAR | R2,223 ZAR | R2,191 ZAR | R2,046 ZAR | R2,062 ZAR | R2,046 ZAR | R2,416 ZAR | R2,416 ZAR | R2,416 ZAR |
| 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 |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Osprey?
Yes! Work meets play with ease at over 40 vacation rentals in Osprey featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Osprey?
Four-legged friends are welcome in Osprey. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there Osprey vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Osprey, available on Airbnb. Make a splash and soak up the sun in style!
Do condo rentals in Osprey have a gym?
Absolutely! We offer over 10 condo rentals with a gym in Osprey. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Osprey?
Osprey has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in condo rentals in Osprey?
Experience the best of Osprey with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Osprey have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Osprey. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Osprey have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Osprey. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Osprey have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Osprey. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Osprey?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 40 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Osprey

Total vacation rentals
Explore 90 vacation rentals in Osprey

Nightly prices starting at
Osprey vacation rentals start at R966 ZAR per night before taxes and fees

Verified guest reviews
Over 1,870 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 of Osprey vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Osprey rentals

4.8 Average rating
Osprey stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- John's Pass
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- Manasota Key Beach
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Englewood Beach
- St Pete Beach
- Myakka River State Park
- North Beach At Fort DeSoto Park
- The Don CeSar
- Lakewood National Golf Club
- Stump Pass Beach State Park




