Osprey holiday rentals

We found 7,508 holiday rentals — enter your dates for availability
Discover a selection of 14 homes and other holiday rentals in Osprey that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Osprey

Showing deals for:11 Dec - 18 Dec

Exterior
Exterior
Exterior
Aerial view
Exceptional
(13 reviews)

Modern Home + Heated Pool + Spa + Walkable Downtown + Short Drive to Beaches

Sarasota

8% off
AU$12,460
for 7 nights, 1 home
AU$1,780 per night
includes taxes & fees
Modern Home + Heated Pool + Spa + Walkable Downtown + Short Drive to Beaches
Gas fire pit by mango tree - w Adirondack chairs
Pool
Private kitchen
Living area
Exceptional
(118 reviews)

Pineapple House - near beaches - private SOUTH facing POOL & HOT TUB - walkable

Sarasota

15% off
AU$3,540
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
Pineapple House - near beaches - private SOUTH facing POOL & HOT TUB - walkable
Room
Private kitchen
Dining
Terrace/patio
Exceptional
(84 reviews)

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Sarasota

8% off
AU$2,645
for 7 nights, 1 home
AU$378 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Private kitchen
Pool
Living area
Outdoor dining
Exceptional
(288 reviews)

Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with secluded HEATED POOL

Sarasota

7% off
AU$2,436
for 7 nights, 1 home
AU$348 per night
includes taxes & fees
Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with secluded HEATED POOL
Fully stocked with any type cookware needed to cook.
Property grounds
Exterior detail
Living area
Exceptional
(103 reviews)

Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood

Sarasota

8% off
AU$1,348
for 7 nights, 1 apartment
AU$193 per night
includes taxes & fees
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Outdoor shower (yes there is one inside also)
Room
Private kitchen
Front House from the street view
Exceptional
(30 reviews)

Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach

Sarasota

5% off
AU$2,995
for 7 nights, 1 room
AU$428 per night
includes taxes & fees
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
Private kitchen
Marina
Interior
Property grounds
Exceptional
(73 reviews)

Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach

Sarasota

7% off
AU$3,041
for 7 nights, 1 home
AU$434 per night
includes taxes & fees
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Living area
Interior
Terrace/patio
Living area
Exceptional
(47 reviews)

🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown

Sarasota

7% off
AU$1,650
for 7 nights, 1 home
AU$236 per night
includes taxes & fees
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Open living room and dining room area.
Pool
Queen Bedroom
Private kitchen
Exceptional
(64 reviews)

Private Sarasota Pool Retreat Near Siesta Key Beach!

Sarasota

7% off
AU$2,613
for 7 nights, 1 home
AU$373 per night
includes taxes & fees
Private Sarasota Pool Retreat Near Siesta Key Beach!
Private kitchen
Pool
Property grounds
Private kitchen
Exceptional
(190 reviews)

LAKEFRONT 2bed/2bath with Heated POOL house, JUST 5 min away SIESTA KEY BEACH!

Sarasota

7% off
AU$2,270
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
LAKEFRONT 2bed/2bath with Heated POOL house, JUST 5 min away SIESTA KEY BEACH!
Living area
Private kitchen
Interior
Interior
Exceptional
(67 reviews)

Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches

Bradenton

7% off
AU$4,539
for 7 nights, 1 home
AU$648 per night
includes taxes & fees
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Room
Private kitchen
Exterior
Dining
Exceptional
(12 reviews)

Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!

Siesta Key

7% off
AU$11,555
for 7 nights, 1 home
AU$1,651 per night
includes taxes & fees
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
3RD LEVEL IS WHERE THE HOME IS LOCATED
BACKYARD OASIS WITH PRIVATE POOL
Private kitchen
Exterior
Exceptional
(52 reviews)

NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded

Siesta Key

8% off
AU$10,617
for 7 nights, 1 home
AU$1,517 per night
includes taxes & fees
NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded
Property grounds
Pool
Living area
Dining
Exceptional
(45 reviews)

New Luxurious Coastal Resort 3-Beedroom 2 Bath Private Pool

Venice

7% off
AU$2,751
for 7 nights, 1 home
AU$393 per night
includes taxes & fees
New Luxurious Coastal Resort 3-Beedroom 2 Bath Private Pool
House of the Sun heated pool overlooks the tennis courts and the Gulf of Mexico.
Our fifth floor deck is a wonderful place to sunbath or enjoy a picnic lunch.
Living area
No need to have a car. Lots of eateries, shops & grocery across the street.
Exceptional
(133 reviews)

BE ON THE B E A C H! 2B/2B GREAT LOCATION!

Siesta Key

8% off
AU$2,779
for 7 nights, 1 apartment
AU$397 per night
includes taxes & fees
BE ON THE B E A C H! 2B/2B GREAT LOCATION!
sliding door in kitchen leads to patio area
additional bar area seating
Pool
Outdoor fire pit. Please note guests are responsible for refilling propane
Exceptional
(129 reviews)

HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes

Sarasota

5% off
AU$3,923
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
King bed
Beach
Living area
Interior
Exceptional
(24 reviews)

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key

7% off
AU$3,597
for 7 nights, 1 apartment
AU$514 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Interior
Private kitchen
Living area
Terrace/patio
Wonderful
(82 reviews)

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

Venice

7% off
AU$1,649
for 7 nights, 1 home
AU$236 per night
includes taxes & fees
Gorgeous Pool house 5 min from the beach, shopping and restaurants I
Exterior
Sports court
Glassed in and screened porch
Terrace/patio
Exceptional
(183 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

7% off
AU$3,232
for 7 nights, 1 apartment
AU$462 per night
includes taxes & fees
Amazing 1 Br/1 Ba Condo at Casa Mar
Exterior
Marina
Property grounds
Living area
Exceptional
(40 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
AU$3,781
for 7 nights, 1 apartment
AU$540 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Room
Pool
Exterior
Terrace/patio
Exceptional
(17 reviews)

New The BLUE HERON 3 bedroom oasis with heated pool

Bradenton

7% off
AU$2,636
for 7 nights, 1 home
AU$377 per night
includes taxes & fees
New The BLUE HERON 3 bedroom oasis with heated pool
Front Entrance
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Boat/Fishing Deck
View of spacious main pool and clubhouse. Dry sauna and gym inside.
Exceptional
(102 reviews)

Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

Siesta Key

5% off
AU$4,748
for 7 nights, 1 apartment
AU$678 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Exterior
Dining
Terrace/patio
Interior
Exceptional
(11 reviews)

Beach House in Venice Florida, welcome to paradise.

Venice

6% off
AU$2,932
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
Beach House in Venice Florida, welcome to paradise.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The historical city of Osprey awaits you

The area's history and live music are just some of the reasons to come on holiday to Osprey. This welcoming city is known for its beaches, bars and gardens. Siesta Key Beach and Lido Beach are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Osprey

Do you want to find things to do during your stay? Venture out of your holiday home and check out everything that makes Osprey a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Mote Marine Laboratory & Aquarium (10.9 mi / 17.5 km)
  • Sarasota Jungle Gardens (12.5 mi / 20.1 km)
  • Stoneybrook Golf & Country Club (1.9 mi / 3 km)
  • Pelican Pointe Golf and Country Club (9.6 mi / 15.4 km)
  • Jacaranda West Country Club (10.9 mi / 17.5 km)
  • Links on Longboat (11.3 mi / 18.1 km)

Exploring the beaches and other natural features in Osprey

Whether you're looking for fun outdoor activities or just want to take in the scenery, Osprey is a great place to get outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Siesta Key Beach (6.2 mi / 10 km)
  • Lido Beach (9.3 mi / 15 km)
  • Jim Neville Marine Preserve (1.6 mi / 2.5 km)
  • Turtle Beach (2.7 mi / 4.4 km)
  • Point of Rocks (4.4 mi / 7.1 km)
  • Crescent Beach (4.8 mi / 7.7 km)

Seasonal weather averages in Osprey

If you're hoping to enjoy some warm-weather activities on your holiday, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

Transport options to and around Osprey

Fly into Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), the closest airport, located 13.8 mi (22.2 km) from the city centre.

Frequently asked questions

What is the best area to stay in Osprey when booking a holiday rental?
When considering a holiday rental in Osprey, Florida, a popular area to stay is near the charming coastal community of Casey Key. This picturesque neighbourhood offers a serene atmosphere and stunning waterfront views, making it an ideal spot for those looking to unwind. Visitors can enjoy the natural beauty of the nearby beaches, such as Nokomis Beach, which is superb for sunbathing or taking a leisurely stroll along the shore.In addition to the beaches, the area is close to the Oscar Scherer State Park, where you can explore scenic trails and observe local wildlife, adding a touch of adventure to your stay. Osprey has a variety of properties available, from quaint cottages to luxurious waterfront homes, ensuring that you can find accommodation that suits your needs and preferences.
Where are the best areas for renting a beach house in Osprey?
For renting a beach house in Osprey, Florida, the area around Casey Key is particularly desirable. This charming barrier island is known for its stunning sandy beaches and a laid-back atmosphere. Properties here often feature direct beach access, spacious decks for outdoor dining, and amenities such as private pools and hot tubs, great for relaxing after a day in the sun. Many of these beach houses also come equipped with modern kitchens and laundry facilities, suiting families or groups looking for a comfortable stay.The nearby Siesta Key, renowned for its powdery white sand beaches, is also a fantastic option. Here, visitors can find a variety of rentals, from beachfront condos to larger family homes, often boasting amenities like beach gear, outdoor showers, and community pools. The vibrant local area offers plenty of dining and shopping choices, making it easy for travellers to enjoy the local culture.Additionally, the proximity to the scenic Myakka River State Park provides opportunities for outdoor activities such as kayaking and hiking, enhancing the appeal of the Osprey area for nature lovers.
What is the most popular type of holiday rental accomodation in Osprey?
In Osprey, holiday houses are the most popular type of holiday rental, with around 116 available in the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor areas, making them ideal for families or groups looking to enjoy the sunny Florida weather. Many of these houses are located near attractions such as the historic Spanish Point and the beautiful beaches along the Gulf Coast.In addition to holiday houses, there are approximately 52 condos and 36 apartments available, offering a more compact living option with amenities like community pools, fitness centres, and easy access to local dining and shopping. For those seeking a quaint escape, several cottages and villas provide a charming and intimate atmosphere, often set in picturesque surroundings.
Are there any family house rentals in Osprey?
In Osprey, Florida, there are numerous family-friendly house rentals available, with around 25 options to choose from. This charming area is known for its proximity to beautiful beaches and vibrant outdoor activities, making it an ideal spot for families. Many of these properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces great for children to play.Visitors can enjoy amenities such as private pools, game rooms, and access to nearby parks. The locale is conveniently situated near attractions like the Oscar Scherer State Park, which offers hiking trails and wildlife viewing, as well as the stunning Gulf Coast beaches, great for a day of sun and sand.
Can I rent a holiday home with a pool or hot tub in Osprey?
In Osprey, there are plenty of holiday homes available for rent that come equipped with pools and hot tubs, with around 32 options to choose from. This charming area, located near the beautiful Gulf Coast of Florida, offers a range of neighbourhoods where travellers can find these properties, including the serene Bay Preserve and the picturesque Osprey Harbour.Guests can expect a variety of amenities in these rentals, such as private pools, relaxing hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens great for preparing meals after a day of exploring. Many properties also feature additional comforts like barbecue grills and outdoor dining spaces, allowing for enjoyable evenings under the stars.
Are there pet-friendly house rentals in Osprey?
In Osprey, Florida, there are several pet-friendly house rentals available, with a good selection to choose from. Many of these properties are equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets.The area offers easy access to beautiful parks and beaches, including nearby Oscar Scherer State Park, which is known for its scenic trails and opportunities for outdoor activities, great for walks with your furry companions. Additionally, the charming waterfront neighbourhood provides a relaxing atmosphere, and many rentals are conveniently located near local shops and dining options, adding to the convenience for travellers.
Are there any remote work holiday rentals in Osprey?
In Osprey, Florida, there are numerous holiday rentals suitable for remote work, with around 168 options available. This charming area, located near the stunning Gulf Coast, offers properties that cater to the needs of remote workers. Many rentals come equipped with high-speed internet and Wi-Fi, ensuring that guests can stay connected while enjoying the serenity of their surroundings.Travellers can expect amenities such as spacious workspaces, comfortable seating areas, and fully equipped kitchens, allowing for both productivity and relaxation. The proximity to beautiful beaches and parks, like the nearby Oscar Scherer State Park, provides excellent opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Osprey?
In Osprey, popular holiday rental amenities include fully-equipped kitchens, allowing guests to prepare their own meals with ease. Onsite parking is also a common feature, providing convenience for those travelling by car. Many properties offer decks or patios, great for enjoying the warm Florida weather and outdoor relaxation. Additionally, coffee and tea makers are typically provided for guests who enjoy their morning brew. Notably, some rentals permit pets, making it easier for travellers to bring their furry friends along for the stay.
When is the best time to visit Osprey for a holiday rental?
The best time to visit Osprey for a holiday rental is during the peak season from February to April, with March being particularly popular. This period attracts sun seekers and outdoor enthusiasts, keen to enjoy the stunning beaches and nature parks that Osprey has to offer. With pleasant temperatures averaging between 15 to 25 degrees Celsius, visitors can comfortably engage in a variety of activities like kayaking, fishing, and exploring the scenic Myakka River State Park.During these months, the area bustles with activity, providing ample opportunities for sightseeing and relaxation. The pleasant climate encourages leisurely strolls along the picturesque Gulf Coast beaches, where you can soak up the sun or enjoy a refreshing swim in the ocean.If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter atmosphere and is superb for enjoying the beauty of Osprey without the crowds. The weather is still warm, making it an excellent time for outdoor adventures and peaceful beach days.Ultimately, your choice of when to visit Osprey will depend on whether you prefer the vibrant energy of peak season or the tranquil charm of the shoulder months.
What are the top attractions in Osprey?
In Osprey, visitors can enjoy a range of attractions that highlight both natural beauty and cultural experiences. The serene Oscar Scherer State Park is a prominent feature, offering hiking trails, wildlife viewing, and access to the lovely South Creek, ideal for canoeing and kayaking. This park is a great spot for nature enthusiasts and those looking to explore Florida's natural habitats.Another top attraction is the historic Spanish Point, an archaeological site that provides insight into the area's history and early Native American cultures. Visitors can wander through beautiful gardens, see historical buildings, and learn about the region's past.For beach lovers, Siesta Key is just a short drive away, famed for its powdery white sands and vibrant beach atmosphere, making it great for sunbathing and water activities. The nearby Legacy Trail is great for cycling and walking, connecting Osprey to Sarasota and providing scenic views along the way.
Are all fees included in the Osprey holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Osprey holiday homes with parking?
Stayz offers a wide selection of holiday homes in Osprey with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Osprey holiday homes?
You can find great discounts on holiday homes in Osprey on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Osprey holiday home booking on Stayz?
To find Osprey holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Osprey?
A long-stay holiday home in Osprey is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Osprey holiday home?
Book your Osprey holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Osprey?
Prices for holiday homes in Osprey vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Osprey to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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