Osprey Village holiday rentals

We found 6,412 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Osprey Village that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Osprey Village

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
Living area
Very good
(8 reviews)

Sarasota Modern Home minutes to Siesta & Downtown

Sarasota

5% off
AU$3,340
for 7 nights, 1 home
AU$477 per night
includes taxes & fees
Sarasota Modern Home minutes to Siesta & Downtown
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
Pool
Wonderful
(45 reviews)

Private Large Pool Getaway Near Siesta Key Gulf Gate Home

Sarasota

5% off
AU$4,125
for 7 nights, 1 home
AU$589 per night
includes taxes & fees
Private Large Pool Getaway Near Siesta Key Gulf Gate Home
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
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!
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
Living area
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
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
Private screened lanai with outdoor seating at Siesta Dunes
Exceptional
(31 reviews)

Siesta Dunes | Private Beach & Pool + Activities

Siesta Key

7% off
AU$6,065
for 7 nights, 1 apartment
AU$866 per night
includes taxes & fees
Siesta Dunes | Private Beach & Pool + Activities
Interior
Exceptional
(28 reviews)

Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach

Sarasota

8% off
AU$5,256
for 7 nights, 1 home
AU$751 per night
includes taxes & fees
Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach
A "close-up" view from the balcony.....
Exceptional
(104 reviews)

Siesta Sands Private Beach | Gulf Views | Htd Pool

Siesta Key

7% off
AU$7,999
for 7 nights, 1 apartment
AU$1,143 per night
includes taxes & fees
Siesta Sands Private Beach | Gulf Views | Htd Pool

  • 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

Choose a holiday rental for your Osprey Village getaway

Learn about the unique charm of Osprey Village with a stay in a holiday home rental. This city has something for everyone. Siesta Key Beach and Lido Beach are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Osprey Village

Do you want to discover attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Osprey Village a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Pelican Pointe Golf and Country Club (9.4 mi / 15.2 km)
  • Mote Marine Laboratory & Aquarium (10.9 mi / 17.6 km)
  • Sarasota Jungle Gardens (12.5 mi / 20.2 km)
  • University Park Country Club (14.5 mi / 23.3 km)
  • Stoneybrook Golf & Country Club (1.8 mi / 3 km)
  • Jacaranda West Country Club (10.8 mi / 17.3 km)

Exploring the natural features in Osprey Village

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Osprey Village is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Siesta Key Beach (6.3 mi / 10.2 km)
  • Lido Beach (9.5 mi / 15.2 km)
  • Turtle Beach (2.8 mi / 4.6 km)
  • Point of Rocks (4.6 mi / 7.3 km)
  • Crescent Beach (4.9 mi / 7.8 km)
  • Nokomis Beach (5 mi / 8.1 km)

Transport to and around Osprey Village

Fly into Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), the closest airport, located 13.8 mi (22.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Osprey Village when booking a holiday rental?
When considering a holiday rental in Osprey Village, Florida, a popular area to stay is near the charming waterfront. This location not only offers beautiful views but also provides easy access to some delightful attractions. Nearby, you can enjoy the serene environment of the Oscar Scherer State Park, which is superb for hiking and birdwatching, or visit the stunning beaches of Siesta Key, renowned for their soft, white sands.The waterfront area typically has a variety of properties available, ranging from cosy cottages to more spacious family homes, making it suitable for different types of travellers. Staying here allows you to experience the best of the local lifestyle while being close to nature and the beautiful Gulf Coast.
What are the top attractions in Osprey Village?
In Osprey Village, visitors can explore several attractions that highlight the area's natural beauty and cultural heritage. Close by is the scenic Oscar Scherer State Park, which offers hiking trails, wildlife viewing opportunities, and access to the lovely South Creek, ideal for kayaking and canoeing. This park is superb for those who enjoy outdoor activities and appreciate Florida's diverse ecosystems.Additionally, the nearby historic site of the Osprey Junction Trailhead provides access to the Legacy Trail, a popular route for biking and walking that stretches through the picturesque landscape of Sarasota County.For those interested in arts and culture, the charming town of Venice is just a short drive away, where visitors can enjoy local shops, restaurants, and the beautiful Venice Beach. The area also boasts cultural attractions such as the Venice Theatre, known for its vibrant community performances.
Are all fees included in the Osprey Village 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 Village holiday homes with parking?
Stayz offers a wide selection of holiday homes in Osprey Village 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 Village holiday homes?
You can find great discounts on holiday homes in Osprey Village 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 Village holiday home booking on Stayz?
To find Osprey Village 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 Village?
A long-stay holiday home in Osprey Village 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 Village holiday home?
Book your Osprey Village 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 Village?
Prices for holiday homes in Osprey Village 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 Village 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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