Osprey Village holiday homes

We found 6,329 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:8 Jan - 15 Jan

Interior
Pool
Beach
Private kitchen
Exceptional
(28 reviews)

Rare private beachfront estate on the Gulf.

Nokomis

8% off
NZ$48,432
for 7 nights, 1 home
NZ$6,919 per night
includes taxes & fees
Rare private beachfront estate on the Gulf.
Luxury Estate By The Bay - Close to Beach image 9
Luxury Estate By The Bay - Close to Beach image 25
Interior
Luxury Estate By The Bay - Close to Beach image 13
Exceptional
(18 reviews)

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

Sarasota

8% off
NZ$18,819
for 7 nights, 1 home
NZ$2,688 per night
includes taxes & fees
Sarasota Bayfront Estate - Sunset Views, Near Crescent Beach & Siesta Key Beach
King bed
Beach
Living area
Interior
Exceptional
(25 reviews)

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

Siesta Key

8% off
NZ$5,282
for 7 nights, 1 apartment
NZ$755 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Interior
Dining
Living area
Private kitchen
Exceptional
(57 reviews)

Sarasota Waterfront Paradise- Location, Location...!!

Sarasota

8% off
NZ$6,051
for 7 nights, 1 home
NZ$864 per night
includes taxes & fees
Sarasota Waterfront Paradise- Location, Location...!!
Exterior
Outdoor dining
Room
Pool
Exceptional
(52 reviews)

LAKE SARASOTA VACATION HOME CABLE TV !!! Sport channels!

Sarasota

8% off
NZ$3,781
for 7 nights, 1 home
NZ$540 per night
includes taxes & fees
LAKE SARASOTA VACATION HOME CABLE TV !!! Sport channels!
Living room with connected enclosed patio
Sundeck on rooftop with partial ocean views
Main bedroom with direct access to enclosed balcony
Plenty of room to host an evening in
Exceptional
(15 reviews)

Sundeck with Ocean View, Private Access to Beach & 500ft to the Village

Siesta Key

8% off
NZ$8,123
for 7 nights, 1 apartment
NZ$1,160 per night
includes taxes & fees
Sundeck with Ocean View, Private Access to Beach & 500ft to the Village
Interior
Interior
Room
Dining
Exceptional
(45 reviews)

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

Sarasota

7% off
NZ$5,673
for 7 nights, 1 home
NZ$810 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Beach side gazebos
2 gazebos with seating to catch the sunsets
Large pool with lounge chairs and BBQ grill and picnic area.
Large Smart TV with cable.
Exceptional
(106 reviews)

Shark Teeth Retreat: Modern Coastal Bliss, Steps to Private Beach, Near Downtown

Venice

23% off
NZ$2,138
for 7 nights, 1 apartment
NZ$305 per night
includes taxes & fees
Shark Teeth Retreat: Modern Coastal Bliss, Steps to Private Beach, Near Downtown
75" TV perfect for movie nights.
Sophisticated and serene Mediterranean beach home.
Living area w/views of pool, jacuzzi and canal offering easy indoor-outdoor flow
Private, heated pool and spa with canal views and your own private dock.
Exceptional
(14 reviews)

Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

Siesta Key

7% off
NZ$13,875
for 7 nights, 1 home
NZ$1,982 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock
Living area
Large 8 person spa
Shed for bikes and pool equipment
Kitchen. All new appliances
Exceptional
(21 reviews)

7 minute walk to Siesta Key beach. Large heated pool/spa. Very private.1/2 acre

Siesta Key

8% off
NZ$16,401
for 7 nights, 1 home
NZ$2,343 per night
includes taxes & fees
7 minute walk to Siesta Key beach. Large heated pool/spa. Very private.1/2 acre
Dining
BACKYARD OASIS WITH PRIVATE POOL
GREAT OUTDOOR SEATING AREA FOR THE WHOLE FAMILY TO ENJOY!
Living area
Exceptional
(52 reviews)

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

Siesta Key

8% off
NZ$15,066
for 7 nights, 1 home
NZ$2,152 per night
includes taxes & fees
NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded
Pool
additional bar area seating
Front (living) room
sliding door in kitchen leads to patio area
Exceptional
(129 reviews)

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

Sarasota

5% off
NZ$5,874
for 7 nights, 1 home
NZ$839 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Interior
5th floor view is spectacular!
Property grounds
Well Kept Pool for  the exclusive use of Crescent Royale Owners and Guests
Exceptional
(79 reviews)

Top Floor Oceanfront View! Fantastic location! Saturday-Saturday only

Siesta Key

7% off
NZ$5,713
for 7 nights, 1 apartment
NZ$816 per night
includes taxes & fees
Top Floor Oceanfront View! Fantastic location! Saturday-Saturday only
Room
Private kitchen
Exterior detail
Dining
Exceptional
(84 reviews)

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

Sarasota

8% off
NZ$3,383
for 7 nights, 1 home
NZ$483 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Terrace/patio
Living area
Room
Private kitchen
Exceptional
(134 reviews)

Lido Beach Walk! One block to beach!

Sarasota

8% off
NZ$2,784
for 7 nights, 1 room
NZ$398 per night
includes taxes & fees
Lido Beach Walk! One block to beach!
Entryway
Living area
Terrace/patio
Interior
Exceptional
(22 reviews)

Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Sarasota

15% off
NZ$5,035
for 7 nights, 1 villa
NZ$719 per night
includes taxes & fees
Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota
Private kitchen
Marina
Living area
Property grounds
Exceptional
(43 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
NZ$4,946
for 7 nights, 1 apartment
NZ$707 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Room
Private kitchen
Exterior detail
Interior
Exceptional
(34 reviews)

Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!

Sarasota

8% off
NZ$3,781
for 7 nights, 1 home
NZ$540 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Room
Sunset Royale Condominiums
Interior
Property grounds
Exceptional
(53 reviews)

Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!

Siesta Key

8% off
NZ$4,109
for 7 nights, 1 apartment
NZ$587 per night
includes taxes & fees
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Glassed in and screened porch
Sports court
Exterior
Interior
Exceptional
(185 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

7% off
NZ$4,163
for 7 nights, 1 apartment
NZ$595 per night
includes taxes & fees
Amazing 1 Br/1 Ba Condo at Casa Mar
Games room
Private kitchen
Room
Interior
Exceptional
(13 reviews)

Renovated Modern Spacious Ranch with Pool near Siesta Key Beach and Downtown SRQ

Sarasota

8% off
NZ$6,095
for 7 nights, 1 home
NZ$871 per night
includes taxes & fees
Renovated Modern Spacious Ranch with Pool near Siesta Key Beach and Downtown SRQ
Big screen TV.
Steps to Siesta Key Beach!
Open concept living room looking toward dining room.
Spacious living room with queen sleeper sofa
Exceptional
(15 reviews)

Steps to Siesta Key Beach! We offer 3-night rentals! Beach gear included!

Siesta Key

8% off
NZ$6,554
for 7 nights, 1 apartment
NZ$936 per night
includes taxes & fees
Steps to Siesta Key Beach! We offer 3-night rentals! Beach gear included!
Exterior
Beach
Dining
Private kitchen
Exceptional
(53 reviews)

Siesta Key Beach Cottage

Siesta Key

7% off
NZ$4,382
for 7 nights, 1 cottage
NZ$626 per night
includes taxes & fees
Siesta Key Beach Cottage
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Front Entrance
Boat/Fishing Deck
Exceptional
(102 reviews)

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

Siesta Key

5% off
NZ$7,115
for 7 nights, 1 apartment
NZ$1,016 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
  • 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

Why visit Osprey Village

  • Outdoor Activities: Enjoy a variety of outdoor pursuits, from leisurely walks to water-based fun, all set against the stunning backdrop of Lake Osprey.
  • Family-Friendly Atmosphere: Osprey Village is perfect for families, offering safe and engaging environments for children and adults alike.
  • Charming Waterfront Living: Experience the tranquil vibe of the village, ideal for relaxation and enjoying picturesque views.
  • Community Spirit: Embrace the friendly and welcoming community that enhances your holiday experience.
  • Urban Parks and Jetties: Explore well-maintained parks and jetties, perfect for sunny day outings and connecting with nature.

Top attractions near Osprey Village

Osprey Village offers a blend of outdoor activities and family-friendly experiences, perfect for a beach holiday. Explore its urban parks and jetties, ideal for a sunny day out. The local attractions provide memorable experiences for travellers seeking a relaxed yet engaging coastal escape, ensuring a delightful holiday in this charming Florida city.

  • Siesta Key Beach: Enjoy the relaxed beach vibes with golden sands and gentle waves, located 10km away from Osprey Village.
  • Heritage Oaks Golf and Country Club: Experience a sophisticated golf course set 13km away from Osprey Village, ideal for a leisurely round.
  • Turtle Beach: Revel in the serene beach atmosphere with inviting sands and surf, situated 5km from Osprey Village.

Things to do recommended for couples

For a romantic getaway in Osprey Village, explore the scenic Myakka River State Park or enjoy a sunset picnic at Casey Key Beach. Indulge in a candlelit dinner at a local seafood restaurant, followed by a stroll along the tranquil shores, creating unforgettable memories together.

Things to do recommended for families

Families can explore the local charm of Osprey Village, with kid-friendly activities like paddle boarding on the scenic waterways and nature walks in nearby reserves. Enjoy local treats and cultural experiences during your stay in this laid-back community.

Things to do recommended for groups

Groups visiting Osprey Village can enjoy a thrilling experience at the TreeUmph. Adventure Course, an exciting zipline and ropes course located 29km away, perfect for outdoor adventures.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Osprey Village

If you’re travelling with a group, family, pets, or planning for an extended stay, be sure to refine your search according to your top priorities. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Osprey Village with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Osprey Village with young kids: Exploring with young kids can be quite demanding. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Osprey Village: For many families, a holiday wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Osprey Village: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Osprey Village

Osprey Village, Florida, offers a delightful escape for families and couples alike. With its charming waterfront living and tranquil atmosphere, visitors can enjoy outdoor activities by Lake Osprey. The village embodies a friendly community spirit, perfect for leisurely strolls and relaxation under the sunny Florida skies. Embrace the laid-back lifestyle and create lasting memories in this inviting destination, ideal for a refreshing holiday experience.

  • Siesta Key: Siesta Key is a charming island city renowned for its sun-drenched beaches and relaxed outdoor ambience. Just 11km from Osprey Village, this locale offers a delightful blend of family-friendly attractions and natural coastal beauty. Visitors can enjoy expansive sandy beaches, explore recreational areas or visit a bustling shopping centre, making it an attractive destination for those seeking a mix of leisure and activity. The picturesque family beach and nearby town neighbourhood add to the island’s appeal, promising a memorable holiday experience.
  • Venice: Venice is a vibrant city that offers a pleasant coastal escape just 11km from Osprey Village. With a focus on outdoor and family experiences, travellers can enjoy its beautiful beach, explore well-maintained recreational areas, or even try their hand at a round of golf on a local course. The blend of natural seaside charm with recreational opportunities makes Venice a compelling choice for those looking to balance relaxation with a touch of adventure.
  • Osprey: Osprey, home to the renowned Osprey Village, is a delightful city that captures the essence of a coastal holiday. It provides a mix of outdoor and family attractions, including inviting beaches and recreational areas, as well as opportunities for a spot of golf. With its accessible local landmarks such as the family beach and town neighbourhood, Osprey offers a well-rounded travel experience that is both relaxing and engaging, ideal for visitors looking to explore the heart of the region.

Best time to go to Osprey Village

If you're planning a trip to Osprey Village, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January62.6°F (17.0°C)Light RainMostly Sunny
February65.1°F (18.4°C)No Rain (Dry)Mostly Sunny
March68.0°F (20.0°C)No Rain (Dry)Sunny
April73.4°F (23.0°C)Light RainMostly Sunny
May77.7°F (25.4°C)Light RainMostly Sunny
June81.7°F (27.6°C)Light RainMostly Sunny
July82.9°F (28.3°C)Light RainMostly Sunny
August83.3°F (28.5°C)Light RainMostly Sunny
September81.5°F (27.5°C)Light RainMostly Sunny
October77.2°F (25.1°C)Light RainMostly Sunny
November70.7°F (21.5°C)No Rain (Dry)Mostly Sunny
December66.6°F (19.2°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is simple

Are you eager to save on your next adventure? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s new Trip Board is designed to help you plan your journeys with ease. Here, you can start fresh trips, pick up where you last left off, or simply review and arrange your travel plans. Any properties you’ve saved or booked will be neatly organised into Potential, Upcoming, or Current Trips. To try out Trip Boards, visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Osprey Village holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Osprey Village to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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