Osprey Village holiday rentals

We found 6,094 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: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
Private kitchen
Pool
Living area
Dining 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
Dining
Private kitchen
Terrace/patio
Exterior detail
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.
Living area
Property grounds
Terrace/patio
Exterior detail
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
Dining
Pool
Living area
Private kitchen
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
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
Interior
Marina
Pool
Private kitchen
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
Private kitchen
Interior
Interior
Dining
Exceptional
(44 reviews)

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

Sarasota

7% off
AU$3,544
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Exterior
Private kitchen
Room
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!
Queen Bedroom
Pool
Open living room and dining room area.
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
Private kitchen
Property grounds
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!
BEDROOM #3 WITH KING SIZE BED & OWN BATHROOM AND SMART TV
BACKYARD OASIS WITH PRIVATE POOL
3RD LEVEL IS WHERE THE HOME IS LOCATED
Private kitchen
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
Dining
Pool
Dining
Interior
Exceptional
(22 reviews)

Southside Bungalow - Sleeps 8 - Pool, Spa & Putting Green

Sarasota

8% off
AU$7,161
for 7 nights, 1 home
AU$1,023 per night
includes taxes & fees
Southside Bungalow - Sleeps 8 - Pool, Spa & Putting Green
Interior
Beach
King bed
Living area
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
Workout equipment and pool table right off of the pool area.
Our fifth floor deck is a wonderful place to sunbath or enjoy a picnic lunch.
Living area
House of the Sun heated pool overlooks the tennis courts and the Gulf of Mexico.
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
Front (living) room
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
Exterior
Beach
Property grounds
Dining
Wonderful
(16 reviews)

Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach

Siesta Key

8% off
AU$4,038
for 7 nights, 1 apartment
AU$577 per night
includes taxes & fees
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Swimming pool by the Gaming room
Screened porch
BBQ and Outdoor patio space
King bedroom
Exceptional
(44 reviews)

Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!

Siesta Key

6% off
AU$3,811
for 7 nights, 1 room
AU$544 per night
includes taxes & fees
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Exterior
Marina
Property grounds
Private kitchen
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
Exterior
Sports court
Terrace/patio
Interior
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
Living area
Interior
Dining
Interior
Exceptional
(44 reviews)

Luxury condo located directly on Siesta Key Beach

Siesta Key

8% off
AU$2,975
for 7 nights, 1 apartment
AU$425 per night
includes taxes & fees
Luxury condo located directly on Siesta Key Beach
Fully stocked coffee bar includes: loose coffee, K-cups, sugars, and more.
Fully stocked kitchen perfect for eating at home.
Guest bedroom downstairs with a queen bed.
Dining room seats 8
Exceptional
(68 reviews)

Ingram House 2

Sarasota

8% off
AU$2,977
for 7 nights, 1 home
AU$425 per night
includes taxes & fees
Ingram House 2
View of spacious main pool and clubhouse. Dry sauna and gym inside.
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Boat/Fishing Deck
Enclosed patio brand new furniture (purchased June 2024)
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!
Interior
Dining
Private kitchen
Exterior
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

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:

  • Mote Marine Laboratory & Aquarium (10.9 mi / 17.6 km)
  • Sarasota Jungle Gardens (12.5 mi / 20.2 km)
  • Stoneybrook Golf & Country Club (1.8 mi / 3 km)
  • Pelican Pointe Golf and Country Club (9.4 mi / 15.2 km)
  • Jacaranda West Country Club (10.8 mi / 17.3 km)
  • Links on Longboat (11.4 mi / 18.3 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)
  • Jim Neville Marine Preserve (1.7 mi / 2.7 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)

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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