Choose from 69 vacation rentals located in Osprey, Florida. Top filters in Osprey include Air conditioner, Internet / Wifi, and Kitchen / Kitchenette. Prices range from $65 to $3,500 per night. Our most popular vacation rental types near Osprey are Condo and Hotel.

Top vacation rentals in Osprey

Home entrance
4.8
Outstanding(52 Reviews)
House
 in Osprey
Pet Friendly Paradise Close To Sarasota-Venice
5 guests · 3 bedrooms · 2 baths
Garden · Pool · Pets allowed

Looking for the perfect place to call home during your trip to Osprey? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Gulf of Mexico
4.8
Outstanding(43 Reviews)
House
 in Nokomis
Casey Key Beach House: A Place to Relax
8 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed

Looking for the perfect place to call home during your trip to Osprey? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Beach view looking south
4.8
Outstanding(33 Reviews)
House
 in Osprey
Idyllic Casey Key Beach House
6 guests · 3 bedrooms · 3 baths
Pool · Pets allowed · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Osprey at Idyllic Casey Key Beach House for $570 for your next trip.

$$$$
vrbo logo
View deal
Property view
4.0
Good(1,172 Reviews)
Hotel
 in Osprey
3star
Casey Key Resorts - Mainland
Pool · Pets allowed · Air conditioner

This Hotel for $135 in Osprey, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal

Search by amenity

Vacation rentals with air conditioning in Osprey

Property grounds
5.0
Outstanding(11 Reviews)
Condo
 in Sarasota
2BR/2BA 1st Floor Condo in Stoneybrook Golf & Country Club
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Osprey, at $81 per night for your next great vacation.

$$$$
vrbo logo
View deal
Pool
4.5
Excellent(19 Reviews)
House
 in Osprey
Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
8 guests · 4 bedrooms · 2 baths
Garden · Pool · Pets allowed

Business stays, family stays, couples stay, getaway vacation, and rental in Osprey at Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi for $206 for your next trip.

$$$$
vrbo logo
View deal
The Sun Kiss on Nokomis beach
4.7
Outstanding(12 Reviews)
House
 in Nokomis
\"The Sun Kiss\" house with private pool, close to public beach Nokomis, Florida
6 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Osprey at \"The Sun Kiss\" house with private pool, close to public beach Nokomis, Florida for $333 for your next trip.

$$$$
vrbo logo
View deal
Interior
5.0
Outstanding(10 Reviews)
House
 in Osprey
Casey Key Paradise
6 guests · 3 bedrooms · 4 baths
Garden · Pets allowed · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Osprey, at $1,517 per night for your next great vacation.

$$$$
vrbo logo
View deal
city photo
Osprey

Osprey travel guide

Let us help you plan your perfect Osprey vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Osprey, and more.

Frequently asked questions

What is the price range for rentals in Osprey?

Vacation rentals in Osprey have a price range between $65-$3,500. The average price for rentals in Osprey is $188 per night.

What are the top things to do in Osprey, FL?

Osprey, FL is a great place to visit, with plenty of fun activities to do. Here are the top four things to do in Osprey, FL:

  • Visit Oscar Scherer State Park
  • Go kayaking or fishing in the Bay
  • Explore the Legacy Trail
  • Take a stroll along the Nokomis Beach
Osprey, FL is a great place to visit, with plenty of fun activities to do. Here are the top four things to do in Osprey, FL:
  • Visit Oscar Scherer State Park
  • Go kayaking or fishing in the Bay
  • Explore the Legacy Trail
  • Take a stroll along the Nokomis Beach

What are the most popular vacation rental amenities in Osprey, FL?

The most popular vacation rental amenities in Osprey, FL are:

  • Fully-equipped kitchen
  • Air conditioning
  • Outdoor patio or balcony
  • Complimentary Wi-Fi
  • Washer and dryer

These amenities provide visitors with all of the comforts of home, allowing them to easily relax and enjoy their vacation. The fully-equipped kitchen, for example, makes it possible for visitors to make their own meals, which can be enjoyed on the outdoor patio or balcony. Additionally, air conditioning, complimentary Wi-Fi, and a washer and dryer ensure that visitors remain comfortable throughout their stay.

Where is Osprey, FL?

Osprey, Florida is located in Sarasota County on the Southwestern coast of the state, along the Gulf of Mexico. It is a small town of just over 4,000 people, and is known for its natural beauty, wildlife, and outdoor activities. Osprey is located just south of the city of Sarasota and north of Venice.

What are the best neighborhoods to visit in Osprey, FL?

The best neighborhoods to visit in Osprey, FL are:

  • Southbay Yacht and Racquet Club
  • Osprey Pointe
  • Osprey Oaks

Each of these neighborhoods offer beautiful waterfront views, and a variety of unique activities and amenities.

What are the popular shopping destinations in Osprey, FL?

The popular shopping destinations in Osprey, FL are:

  • The Mall at University Town Center
  • Westfield Sarasota Square
  • Costco
  • Target

Is Osprey, FL safe to travel to?

Osprey, FL is generally a safe place to travel to. Here are some of the safety measures in place:

  • Robust police presence
  • Well-lit streets
  • Low crime rate

Overall, Osprey, FL is a safe and secure place to visit.

What is the culture like in Osprey, FL?

Osprey, FL is a small town located in Sarasota County, Florida. It is known for its beautiful beaches and diverse culture. Here are five aspects of the culture in Osprey, FL:

  • The area has a strong sense of community and many local events.
  • There is a large focus on the outdoors, with plenty of outdoor activities available.
  • The town has a rich history and a variety of historical sites.
  • The area is known for its art and culture, with many art galleries and museums.
  • The town has a vibrant nightlife, with many bars and restaurants.

Where can I find affordable accommodation in Osprey, FL?

Osprey, FL offers a variety of affordable accommodation options. Here are a few of the best options:

  • The Osprey Inn: A cozy inn located in the heart of Osprey, with rooms starting at just $50 per night.
  • The Osprey Beach Resort: A luxurious beachfront resort with rooms starting at $75 per night.
  • The Osprey Lodge: An intimate lodge located near the beach, with rooms starting at $60 per night.
  • The Osprey Hotel: A modern hotel located in downtown Osprey, with rooms starting at $65 per night.

No matter what your budget is, you're sure to find the perfect accommodation in Osprey, FL!

How can I get around in Osprey, FL?

You can get around in Osprey, FL in a variety of ways:

  • Walking
  • Biking
  • Public Transportation
  • Ridesharing

Osprey is a great city to explore, so make sure to get out and enjoy all that it has to offer!

What are the must-visit tourist attractions in Osprey, FL?

Osprey, FL is a great place to visit for tourists. There are plenty of attractions to explore, including the following:

  • Oscar Scherer State Park
  • Legacy Trail
  • Nokomis Beach
  • Casey Key Fish House

Oscar Scherer State Park is a great place for nature lovers, with plenty of trails, lakes, and wildlife. The Legacy Trail is a great place to bike or walk, and it offers stunning views of the area. Nokomis Beach is a great spot for swimming and relaxing, and Casey Key Fish House is a great spot for seafood lovers.

What do I need to know before visiting Osprey, FL?

Before visiting Osprey, FL, it's important to know that the town is located on the Gulf Coast, that it is a popular spot for golfers, and that it has plenty of outdoor activities.

  • Osprey is located on the Gulf Coast
  • Osprey is a popular spot for golfers
  • Osprey has plenty of outdoor activities

What are the most popular vacation rental amenities in Osprey?

  • Air conditioner
  • Internet / Wifi
  • Kitchen / Kitchenette

Explore near Osprey

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration

Keep exploring