Osprey Village holiday homes

We found 6,151 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:20 Nov - 27 Nov

Living area
Pool
Private kitchen
Exterior
Exceptional
(12 reviews)

Beautiful Waterfront House w/ Pool, 7 min to the Beach

Nokomis

8% off
NZ$4,519
for 7 nights, 1 home
NZ$646 per night
includes taxes & fees
Beautiful Waterfront House w/ Pool, 7 min to the Beach
Pool
Living area
Dining
Outdoor dining
Exceptional
(81 reviews)

Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate

Sarasota

7% off
NZ$3,204
for 7 nights, 1 cottage
NZ$458 per night
includes taxes & fees
Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
living room area/ceiling fans throughout home
Kitchen area with open concept…to right is door to car port/screened porch
55 inch smart TV.  Bring your Netflix login!
2 bikes (w/ bike lock) avail for your use, enjoy a cruise in the neighborhood
Exceptional
(30 reviews)

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

Sarasota

5% off
NZ$2,846
for 7 nights, 1 cottage
NZ$407 per night
includes taxes & fees
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks, large backyard
Private kitchen
Marina
Interior
Property grounds
Exceptional
(72 reviews)

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

Sarasota

7% off
NZ$3,592
for 7 nights, 1 home
NZ$513 per night
includes taxes & fees
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Property grounds
Marina
Dining
Pool
Wonderful
(59 reviews)

Private Heated Pool Home Near Downtown & Legacy Trail

Sarasota

5% off
NZ$3,031
for 7 nights, 1 home
NZ$433 per night
includes taxes & fees
Private Heated Pool Home Near Downtown & Legacy Trail
Living area
Property grounds
Fully stocked with any type cookware needed to cook.
Terrace/patio
Exceptional
(101 reviews)

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

Sarasota

8% off
NZ$1,506
for 7 nights, 1 apartment
NZ$215 per night
includes taxes & fees
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Pool
Property grounds
Room
Private kitchen
Exceptional
(53 reviews)

BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

Sarasota

7% off
NZ$3,380
for 7 nights, 1 villa
NZ$483 per night
includes taxes & fees
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Private kitchen
Property grounds
Room
Interior
Exceptional
(11 reviews)

Pet-Friendly 1BR Sarasota Florida Vacation Rental, Patio, Near Beaches, 2 Guests

Sarasota

7% off
NZ$1,189
for 7 nights, 1 apartment
NZ$170 per night
includes taxes & fees
Pet-Friendly 1BR Sarasota Florida Vacation Rental, Patio, Near Beaches, 2 Guests
Exterior
Private kitchen
Living area
Room
Exceptional
(11 reviews)

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

Siesta Key

7% off
NZ$16,168
for 7 nights, 1 home
NZ$2,310 per night
includes taxes & fees
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
Art deco window in front of sun room with table and chairs
Interior
Interior
Welcome to Chasing The Sun
Exceptional
(25 reviews)

Adorable Lido Beach Home- walk to beach and St. Armand's

Sarasota

8% off
NZ$5,657
for 7 nights, 1 home
NZ$808 per night
includes taxes & fees
Adorable Lido Beach Home- walk to beach and St. Armand's
Interior
Private kitchen
Room
Living area
Exceptional
(5 reviews)

Central City Condominiums #203 2BR/2BA

Sarasota

7% off
NZ$1,948
for 7 nights, 1 apartment
NZ$278 per night
includes taxes & fees
Central City Condominiums #203 2BR/2BA
Front (living) room
additional bar area seating
sliding door in kitchen leads to patio area
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
NZ$5,924
for 7 nights, 1 home
NZ$846 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Queen Bedroom
Pool
Open living room and dining room area.
Dining room table fix 6 guests.
Exceptional
(63 reviews)

Private Sarasota Pool Retreat Near Siesta Key Beach!

Sarasota

7% off
NZ$3,163
for 7 nights, 1 home
NZ$452 per night
includes taxes & fees
Private Sarasota Pool Retreat Near Siesta Key Beach!
Living room taken from master bedroom door
View of Sarasota Bay from balcony
View from roof of pool, dock, hot tub
Kitchen
Wonderful
(161 reviews)

Palm Bay Club Bayside Well-Priced Condo on Siesta Key 2 bed and 2 bath unit

Siesta Key

8% off
NZ$4,464
for 7 nights, 1 apartment
NZ$638 per night
includes taxes & fees
Palm Bay Club Bayside Well-Priced Condo on Siesta Key 2 bed and 2 bath unit
Room
Large Living Space with HD Flat Screen TV, Cable, DVD Player and Wi-Fi
Living area
Walk through Kitchen with all amenities
Wonderful
(135 reviews)

Venice Island / Venice Beach Luxury Villa

Venice

7% off
NZ$2,593
for 7 nights, 1 villa
NZ$370 per night
includes taxes & fees
Venice Island / Venice Beach Luxury Villa
Property grounds
Beach
Dining
Exterior
Wonderful
(16 reviews)

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

Siesta Key

8% off
NZ$4,732
for 7 nights, 1 apartment
NZ$676 per night
includes taxes & fees
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Dining area from living area
Kitchen renovated Fall 2013/Spring 2014
activity area in main building
Room
Exceptional
(107 reviews)

Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price

Siesta Key

6% off
NZ$4,190
for 7 nights, 1 apartment
NZ$599 per night
includes taxes & fees
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Arial view of the building - right on the beach!
Beach
Living area
King bed
Exceptional
(23 reviews)

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

Siesta Key

8% off
NZ$6,249
for 7 nights, 1 apartment
NZ$893 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Private kitchen
Marina
Exterior
Property grounds
Exceptional
(38 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
NZ$4,623
for 7 nights, 1 apartment
NZ$660 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Living area
Private kitchen
Exterior detail
Room
Exceptional
(34 reviews)

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

Sarasota

7% off
NZ$2,940
for 7 nights, 1 home
NZ$420 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Front of building
Front door and porch area
New king bed
Robin Hood Rentals golf carts bikes etc
Exceptional
(15 reviews)

Siesta Key Village • Pool • Walk to Beach • Pets

Siesta Key

8% off
NZ$4,102
for 7 nights, 1 apartment
NZ$586 per night
includes taxes & fees
Siesta Key Village • Pool • Walk to Beach • Pets
Property grounds
Sunset Royale Condominiums
Room
Interior
Exceptional
(52 reviews)

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

Siesta Key

7% off
NZ$3,651
for 7 nights, 1 apartment
NZ$522 per night
includes taxes & fees
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Beach
Property grounds
Exterior detail
Private kitchen
Exceptional
(28 reviews)

NOKOMIS BEACH BUNGALOW 227

Nokomis

7% off
NZ$1,666
for 7 nights, 1 home
NZ$238 per night
includes taxes & fees
NOKOMIS BEACH BUNGALOW 227
Sports court
Private kitchen
Pool
Terrace/patio
Exceptional
(8 reviews)

Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

Sarasota

7% off
NZ$2,614
for 7 nights, 1 home
NZ$373 per night
includes taxes & fees
Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
  • 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 Venice 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)
  • Tatum Ridge Golf Links (11.1 mi / 17.8 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)
  • Venice Beach (7.3 mi / 11.7 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)

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 most popular type of holiday home accommodation in Osprey Village?
Based on our data, houses are considered the most popular type of holiday property in Osprey Village. But naturally, everyone's idea of an epic stay will differ. Bookabach has holiday homes of all shapes and sizes, and we'll help you to find the best fit for your needs.
How much does it cost to rent a holiday home in Osprey Village?
Length of stay, season and property type are some of the things that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal escape. From comfy cabins to sprawling villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Osprey Village?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Click on your Osprey Village travel dates to view your options on Bookabach. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the amenities and features you need.
Are there pet-friendly holiday homes in Osprey Village?
Yes, there are. You'll have your pick of nine holiday homes that allow pets in Osprey Village. Lots of our pet-friendly holiday homes even have an outdoor area for your furry pal to play in, special dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find a holiday home on Bookabach that's pawfect.
Can I rent a house with a pool in Osprey Village?
Tick the "pool" box in our handy filter tool and take your pick of four houses with private pools in Osprey Village on Bookabach. Gentle soak, ball games or noodle joust? Downtime is up to you when your holiday home has its own swimming pool.
What are popular home amenities in Osprey Village?
The most popular home amenities people are searching for in Osprey Village are a fireplace, a garden and a barbecue grill. Whether you're going on holiday with buddies, family or even pets, Bookabach holiday homes come with the best amenities for hanging out with the people who matter most.
Are there large group holiday homes in Osprey Village?
Take your pick of six Bookabach holiday properties in Osprey Village that can host a group of five or more guests. You'll get all the space and privacy you need to hang out with the people you're holidaying with — and no one else.
Are there holiday homes in Osprey Village that welcome kids?
With nine family-friendly holiday homes available in Osprey Village, now is a superb time to introduce your little ones to the pleasures of travel. Check our "Properties good for families" filter to look for stays packed with conveniences perfect for families on the move, such as full kitchens, outdoor spaces, bunk beds and hot tubs.
What are the top attractions for families in Osprey Village?
If you're on holiday with the kids, include these family-friendly attractions in Osprey Village on your must-see list:
  • Oscar Scherer State Park
  • Historic Spanish Point
Are there one-bedroom holiday homes in Osprey Village?
Yes, Osprey Village has two one-bedroom homes on offer. Typically situated in desirable areas thanks to their smaller size, a one-bedroom home is great if you're travelling with your partner or a pal. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you'll be able to kick back and relax while enjoying this amazing destination.
Can I find two-bedroom holiday homes in Osprey Village?
Pick from four two-bedroom holiday homes in Osprey Village. Settle the kids into the second room or maybe fill it with a couple of your best friends. There's a comfy spot for whoever's fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Osprey Village?
Whether you want to keep up with the latest headlines, check emails or surf your social networks, there are two holiday homes with WiFi in Osprey Village. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Osprey Village?
Choose from nine holiday homes with air conditioning in Osprey Village providing that cooling breeze and extra element of comfort. Simply enter your dates of travel and then use our handy filters to help you find stays with air conditioning.
How old do you have to be to rent a holiday home in Osprey Village?
We advise checking with the Osprey Village holiday property you're looking at on Bookabach as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Osprey Village for?
It's up to the Osprey Village property. To look at a list of options offering extended stays, simply enter your dates and number of guests into Bookabach. Enjoy having the whole property to yourself, along with comforts such as air conditioning, a fully-equipped kitchen and an outdoor space where the kids can play. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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