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Holiday homes in Osprey

Enjoy your stay and find the best Holiday homes in Osprey at affordable prices

Searching for a holiday home in Osprey (Florida)? Explore a great selection of vacation homes in Osprey to find the one that best fits to your needs, starting from $62.66 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Osprey and region (20 miles)
Cozy 2BR Florida Home Near the Shore! in Osprey, USA

Cozy 2BR Florida Home Near the Shore!

Holiday home in Osprey, Florida
Set in Osprey, 24 km from John and Mable Ringling Museum of Art, 24 km from The John and Mable Ringling Museum of Art and 11 km from Venice Theatre, C...
  • Parking

no reviews

from $249.33 Show details »

King Bed & Patio, Minutes to the Beach in Osprey, USA

King Bed & Patio, Minutes to the Beach

Villa in Osprey, Florida
Set in Osprey, 24 km from John and Mable Ringling Museum of Art and 24 km from The John and Mable Ringling Museum of Art, NEW 2 Bedroom with King Bed ...
  • Parking

no reviews

from $84.60 Show details »

Pool, Hot tub, Close to Beaches, Shopping, More! in Osprey, USA

Pool, Hot tub, Close to Beaches, Shoppin...

Holiday home in Osprey, Florida , Bayview Avenue
Situated 25 km from John and Mable Ringling Museum of Art, Pool, Hot tub, Close to Beaches, Shopping, More! features accommodation in Osprey with acce...
  • Parking
  • Pets allowed
  • Family rooms
  • Swimming pool
  • Swimming Pool

no reviews

from $297.66 Show details »

New Custom Smart Home Sarasota Family Getaway in Osprey, USA

New Custom Smart Home Sarasota Family Ge...

Holiday home in Osprey, Florida , 2016 Preymore Street
New Custom Smart Home Sarasota Family Getaway, a property with a terrace, is situated in Osprey, 22 km from The John and Mable Ringling Museum of Art,...
  • Parking
  • Family rooms

Exceptional 5 Reviews 9.8

from $322.50 Show details »

Sarasota - Dunmore 8730 in Sarasota, USA

Sarasota - Dunmore 8730

Holiday home in Sarasota near Osprey, Florida , 8730 Dunmore Drive
Located in Sarasota, Sarasota - Dunmore 8730 provides accommodation with a private pool.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $428.40 Show details »

Spacious OASIS Updated Home 3 bed 2 bath -7 min to Nokomis Beach in Nokomis, USA

Spacious OASIS Updated Home 3 bed 2 bath...

Holiday home in Nokomis near Osprey, Florida , 120 Raphael Place
Located in Nokomis, 28 km from The John and Mable Ringling Museum of Art, 8.6 km from Venice Theatre and 22 km from Sarasota Opera, Spacious OASIS Upd...
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 9 Reviews 9.7

from $242.14 Show details »

Bay Tree Beach Side in Sarasota, USA

Bay Tree Beach Side

Holiday home in Sarasota near Osprey, Florida
Bay Tree Beach Side is a beachfront property situated in Sarasota, 21 km from John and Mable Ringling Museum of Art and 21 km from The John and Mable ...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $211.23 Show details »

Casa Margaritaville in Nokomis, USA

Casa Margaritaville

Holiday home in Nokomis near Osprey, Florida , Monet Drive
Featuring an outdoor swimming pool, Casa Margaritaville provides accommodation in Nokomis with free WiFi and pool views.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

no reviews

from $306.94 Show details »

Sarasota Villa with Pool Access about 4 Mi to Beach! in Sarasota, USA

Sarasota Villa with Pool Access about 4...

Villa in Sarasota near Osprey, Florida
Set in Sarasota, 21 km from John and Mable Ringling Museum of Art and 21 km from The John and Mable Ringling Museum of Art, Sarasota Villa with Pool A...
  • Parking
  • Fitness centre

Superb 6 Reviews 9.5

from $183.86 Show details »

Huge Pool, Roomy, Close to Beaches, Shops, Restaurants! in Nokomis, USA

Huge Pool, Roomy, Close to Beaches, Shop...

Holiday home in Nokomis near Osprey, Florida , Monet Place
Set in Nokomis, Huge Pool, Roomy, Close to Beaches, Shops, Restaurants! offers accommodation with a private pool and free WiFi.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $238.80 Show details »

LUX VILLAs on beautiful Palmer Ranch in Vamo, USA

LUX VILLAs on beautiful Palmer Ranch

Villa in Vamo near Osprey, Florida , 3635 White Pine Court
Situated in Vamo, LUX VILLAs on beautiful Palmer Ranch offers a terrace with pool and lake views, as well as a year-round outdoor pool, fitness centre...
  • Parking
  • Restaurant
  • Pets allowed
  • Fitness centre
  • Family rooms

Fabulous 49 Reviews 8.9

from $250.94 Show details »

Village des Pins 3645, 2 Bedrooms, Pool Access, WiFi, Hot Tub, Sleeps 4 in Sarasota, USA

Village des Pins 3645, 2 Bedrooms, Pool...

Holiday home in Sarasota near Osprey, Florida , 3645 White Pine Court
Boasting a hot tub, Village des Pins 3645, 2 Bedrooms, Pool Access, WiFi, Hot Tub, Sleeps 4 is set in Sarasota.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 4 Reviews 9.2

from $230.14 Show details »

Sunny Sarasota Villa with Lanai Less Than 5 Mi to Beach in Sarasota, USA

Sunny Sarasota Villa with Lanai Less Tha...

Villa in Sarasota near Osprey, Florida
Within 20 km of John and Mable Ringling Museum of Art and 21 km of The John and Mable Ringling Museum of Art, Sunny Sarasota Villa with Lanai Less Tha...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 4 Reviews 8.8

from $112.00 Show details »

Sunny Sarasota Oasis with Lanai and Community Pool! in Sarasota, USA

Sunny Sarasota Oasis with Lanai and Comm...

Villa in Sarasota near Osprey, Florida
Sarasota Oasis with Lanai and Community Hot Tub! is set in Sarasota, 20 km from The John and Mable Ringling Museum of Art, 15 km from Sarasota Opera, ...
  • Parking

Exceptional 1 Reviews 10.0

from $169.00 Show details »

Welcome to The Bray Escape 4 miles to Siesta Key in Sarasota, USA

Welcome to The Bray Escape 4 miles to Si...

Holiday home in Sarasota near Osprey, Florida , 7995 Wright Avenue
Welcome to The Bray Escape 4 miles to Siesta Key, a property with a garden, a bar and a tennis court, is set in Sarasota, 19 km from The John and Mabl...
  • Parking
  • Pets allowed
  • Bar
  • Family rooms

Exceptional 14 Reviews 9.8

from $232.42 Show details »

Pet-Friendly, King Bed, Close to Siesta Beach, Restaurants, Shopping in Sarasota, USA

Pet-Friendly, King Bed, Close to Siesta...

Holiday home in Sarasota near Osprey, Florida , Eugene Street
Within 19 km of John and Mable Ringling Museum of Art and 19 km of The John and Mable Ringling Museum of Art, Pet-Friendly, King Bed, Close to Siesta ...
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $174.80 Show details »

Beach house on the sailboat water on Little Sarasota Bay in Sarasota, USA

Beach house on the sailboat water on Lit...

Holiday home in Sarasota near Osprey, Florida , 8115 Midnight Pass Road
Featuring a spa bath, Beach house on the sailboat water on Little Sarasota Bay is located in Sarasota.
  • Parking
  • Pets allowed

no reviews

from $369.00 Show details »

Cozy home in Gulf Gate in Sarasota, USA

Cozy home in Gulf Gate

Holiday home in Sarasota near Osprey, Florida , 2206 Hively Street
Situated 19 km from John and Mable Ringling Museum of Art, 19 km from The John and Mable Ringling Museum of Art and 13 km from Sarasota Opera, Cozy ho...
  • Parking

Superb 29 Reviews 9.4

from $128.25 Show details »

Cozy family retreat minutes away from Siesta Key in Sarasota, USA

Cozy family retreat minutes away from Si...

Holiday home in Sarasota near Osprey, Florida
Cozy family retreat minutes away from Siesta Key in Sarasota provides accommodation with free WiFi, 19 km from John and Mable Ringling Museum of Art, ...
  • Parking
  • Fitness centre
  • Indoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $239.86 Show details »

Cozy Tropical Bungalow Duplex with Heated Pool in Sarasota, USA

Cozy Tropical Bungalow Duplex with Heate...

Holiday home in Sarasota near Osprey, Florida , 1140 Crescent Street
Situated in Sarasota, 400 metres from Crescent Beach and 1.6 km from Turtle Beach, Cozy Tropical Bungalow Duplex with Heated Pool offers free WiFi, a ...

Very good 7 Reviews 8.6

from $251.14 Show details »

Crescent Street 1138 B, Walk to the beach, Pool, 1 Bedroom, Pet Friendly in Siesta Key, USA

Crescent Street 1138 B, Walk to the beac...

Holiday home in Siesta Key near Osprey, Florida , 1138 Crescent Street
Crescent Street 1138 B, Walk to the beach, Pool, 1 Bedroom, Pet Friendly is set in Siesta Key, 1.6 km from Turtle Beach, 18 km from John and Mable Rin...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 13 Reviews 8.1

from $224.00 Show details »

Crescent Street 1138 A, pet-friendly, 2 bedrooms, Pool, Walk to the beach in Siesta Key, USA

Crescent Street 1138 A, pet-friendly, 2...

Holiday home in Siesta Key near Osprey, Florida , 1138 Crescent Street
Situated in Siesta Key and only 400 metres from Crescent Beach, Crescent Street 1138 A, pet-friendly, 2 bedrooms, Pool, Walk to the beach features acc...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 4 Reviews 7.7

from $307.33 Show details »

Crescent Street Manor in Siesta Key, USA

Crescent Street Manor

Holiday home in Siesta Key near Osprey, Florida , 1138 Crescent Street
Featuring a private pool and pool views, Crescent Street Manor is located in Siesta Key.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $333.33 Show details »

Short distance to Beach, Shopping and Restaurants! in Sarasota, USA

Short distance to Beach, Shopping and Re...

Holiday home in Sarasota near Osprey, Florida , Bispham Road
Short distance to Beach, Shopping and Restaurants!, a property with barbecue facilities, is located in Sarasota, 18 km from The John and Mable Ringlin...
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $178.80 Show details »

Crescent Beach Villas in Siesta Key, USA

Crescent Beach Villas

Villa in Siesta Key near Osprey, Florida , 1126 Crescent Street
Located in Siesta Key, 300 metres from Crescent Beach and 1.6 km from Turtle Beach, Crescent Street Villas by Beachside Management provides accommodat...
  • Parking
  • Family rooms
  • Tea/Coffee maker
  • Shower
  • TV

Good 24 Reviews 7.9

from $293.82 Show details »

Number of Holiday homes in Osprey 282
Number of guest ratings 1240
Average price per night $387.60
Lowest price per night $62.66
Highest price per night $1.286.88

Most popular Holiday-homes in Osprey

The most popular Holiday-homes in Osprey based on average guest rating (Top 10).

Cheapest Holiday-homes in Osprey

The cheapest Holiday-homes in Osprey based on room rate per night (Top 10).

Most booked Holiday-homes in Osprey

The most booked Holiday-homes in Osprey based on popularity with guests (Top 10).

Holiday homes in Osprey (Florida), comfortable and familiar

Staying in a holiday or vacation home in Osprey can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Osprey for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Osprey should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com