Osprey holiday rentals

We found 7,841 holiday rentals — enter your dates for availability
Discover a selection of 13 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:29 Jan - 5 Feb

Pool
Exceptional
(28 reviews)

Rare private beachfront estate on the Gulf.

Nokomis

8% off
AU$38,405
for 7 nights, 1 home
AU$5,486 per night
includes taxes & fees
Rare private beachfront estate on the Gulf.
Pool
Exceptional
(12 reviews)

The Golden Palms

Sarasota

21% off
AU$15,920
for 7 nights, 1 home
AU$2,274 per night
includes taxes & fees
The Golden Palms
Picture #1
Exceptional
(83 reviews)

Jamaica Royale | 3 Pools, Beach & Free Activities

Siesta Key

7% off
AU$5,201
for 7 nights, 1 apartment
AU$743 per night
includes taxes & fees
Jamaica Royale | 3 Pools, Beach & Free Activities
Luxury Estate By The Bay - Close to Beach image 25
Exceptional
(18 reviews)

Sarasota Bayfront Estate - Sunset Views, Near Crescent Beach & Siesta Key Beach

Sarasota

8% off
AU$14,899
for 7 nights, 1 home
AU$2,128 per night
includes taxes & fees
Sarasota Bayfront Estate - Sunset Views, Near Crescent Beach & Siesta Key Beach
Dining table right off the kitchen.
Exceptional
(149 reviews)

Lulu’s Loggerhead, Heated Pool, Walk to Village

Siesta Key

7% off
AU$5,484
for 7 nights, 1 apartment
AU$783 per night
includes taxes & fees
Lulu’s Loggerhead, Heated Pool, Walk to Village
Kitchen area with open concept…to right is door to car port/screened porch
Exceptional
(31 reviews)

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks, large backyard

Sarasota

5% off
AU$3,062
for 7 nights, 1 cottage
AU$437 per night
includes taxes & fees
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks, large backyard
Interior
Exceptional
(45 reviews)

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

Sarasota

7% off
AU$4,744
for 7 nights, 1 home
AU$678 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
BACKYARD OASIS WITH PRIVATE POOL
Exceptional
(52 reviews)

Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach

Siesta Key

8% off
AU$16,355
for 7 nights, 1 home
AU$2,336 per night
includes taxes & fees
Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach
Enjoy your morning coffee and cereal in the backyard with singing Seaside Sparrows....
Exceptional
(47 reviews)

Perfect Location, Dog Friendly, Mins to Siesta Key

Sarasota

7% off
AU$4,251
for 7 nights, 1 home
AU$607 per night
includes taxes & fees
Perfect Location, Dog Friendly, Mins to Siesta Key
Living area
Exceptional
(10 reviews)

2 Primary Suites | FREE Pool Heat | Great Beaches

Sarasota

26% off
AU$5,203
for 7 nights, 1 home
AU$743 per night
includes taxes & fees
2 Primary Suites | FREE Pool Heat | Great Beaches
Kitchen with a giant island and seating for four. Cooking essentials are stocked
Exceptional
(41 reviews)

A Whale of a Good Time!

Sarasota

8% off
AU$5,143
for 7 nights, 1 home
AU$735 per night
includes taxes & fees
A Whale of a Good Time!
Catch dinner at the fishing pier!
Wonderful
(46 reviews)

Poolside Style, Beachside Soul at SK's Bay Oaks!

Siesta Key

7% off
AU$3,825
for 7 nights, 1 apartment
AU$546 per night
includes taxes & fees
Poolside Style, Beachside Soul at SK's Bay Oaks!
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
Wonderful
(17 reviews)

Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit

Bradenton

8% off
AU$9,637
for 7 nights, 1 home
AU$1,377 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Terrace/patio
Exceptional
(8 reviews)

For family fun or a romantic escape close to sarasota and the area"s beaches

Bradenton

9% off
AU$2,602
for 7 nights, 1 villa
AU$372 per night
includes taxes & fees
For family fun or a romantic escape close to sarasota and the area"s beaches
Large living area with million dollar views of the Gulf of Mexico!
Excellent
(13 reviews)

Ocean Views! Across from Siesta Beach, Heated Pool

Siesta Key

7% off
AU$6,264
for 7 nights, 1 apartment
AU$895 per night
includes taxes & fees
Ocean Views! Across from Siesta Beach, Heated Pool
Enjoy evenings on Siesta with a dip in the heated pool
Exceptional
(62 reviews)

Walk to Beach + Village, Beach Gear Included, Pool

Siesta Key

7% off
AU$5,731
for 7 nights, 1 apartment
AU$819 per night
includes taxes & fees
Walk to Beach + Village, Beach Gear Included, Pool
Exterior
Exceptional
(44 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
AU$3,865
for 7 nights, 1 apartment
AU$552 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Picture #1
Wonderful
(65 reviews)

2-Story Townhome: Steps from the Sand & Gulf Views

Siesta Key

7% off
AU$6,378
for 7 nights, 1 apartment
AU$911 per night
includes taxes & fees
2-Story Townhome: Steps from the Sand & Gulf Views
Enjoy morning coffee or evening sunsets on the shared bayfront patio�—complete with stunning water views.
Exceptional
(19 reviews)

Siesta Key Base | Walk to Beach | Free Activities

Siesta Key

7% off
AU$3,680
for 7 nights, 1 apartment
AU$526 per night
includes taxes & fees
Siesta Key Base | Walk to Beach | Free Activities
Enjoy the heated community pool, just steps from the condo
Exceptional
(7 reviews)

Dock Views, Near Beach, Heated Pool, Private Beach

Siesta Key

7% off
AU$3,912
for 7 nights, 1 apartment
AU$559 per night
includes taxes & fees
Dock Views, Near Beach, Heated Pool, Private Beach
Pool
Excellent
(156 reviews)

Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL

Sarasota

8% off
AU$1,201
for 7 nights, 1 room
AU$172 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Complex heated pool and private tennis court overlooking Crescent Beach!. (complex aerial view). What are you waiting for?!!
Wonderful
(145 reviews)

House of Sun: Beachfront | VIP Perks | Bunkbeds

Siesta Key

7% off
AU$8,339
for 7 nights, 1 apartment
AU$1,191 per night
includes taxes & fees
House of Sun: Beachfront | VIP Perks | Bunkbeds
Dining
Excellent
(26 reviews)

Centrally Located Charming Beach Suite in Sarasota

Sarasota

8% off
AU$1,103
for 7 nights, 1 apartment
AU$158 per night
includes taxes & fees
Centrally Located Charming Beach Suite in Sarasota
Outdoor dining
Very good
(164 reviews)

SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail

Sarasota

8% off
AU$1,201
for 7 nights, 1 room
AU$172 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail

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  • 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:

  • Pelican Pointe Golf and Country Club (9.6 mi / 15.4 km)
  • Mote Marine Laboratory & Aquarium (10.9 mi / 17.5 km)
  • Sarasota Jungle Gardens (12.5 mi / 20.1 km)
  • University Park Country Club (14.5 mi / 23.3 km)
  • Stoneybrook Golf & Country Club (1.9 mi / 3 km)
  • Jacaranda West Country Club (10.9 mi / 17.5 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)
  • 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)
  • Nokomis Beach (5.1 mi / 8.2 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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