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Holiday homes in Osprey (Page 2)

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 Tropical Bungalow with Heated Pool in Sarasota, USA

Cozy Tropical Bungalow with Heated Pool

Holiday home in Sarasota near Osprey, Florida , 1144 Crescent Street
Located in Sarasota, 200 metres from Crescent Beach and 1.7 km from Turtle Beach, Cozy Tropical Bungalow with Heated Pool provides accommodation with ...
  • Street parking

Very good 10 Reviews 8.3

from $210.00 Show details »

One Ocean - B 1103 in Sarasota, USA

One Ocean - B 1103

Holiday home in Sarasota near Osprey, Florida , 1103 Crescent Street
One Ocean - B 1103 is set in Sarasota, 1.7 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art, as well as 18 km from The John and ...
  • Parking

Fabulous 11 Reviews 8.7

from $218.53 Show details »

One Ocean - A 1101 in Sarasota, USA

One Ocean - A 1101

Holiday home in Sarasota near Osprey, Florida , 1101 Crescent Street
One Ocean - A 1101 is located in Sarasota, 1.7 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art, as well as 18 km from The John ...
  • Parking
  • Air conditioning
  • Refrigerator
  • Seating Area
  • Microwave

Fabulous 13 Reviews 8.8

from $203.55 Show details »

Crescent Beach 1015 #4 in Sarasota, USA

Crescent Beach 1015 #4

Holiday home in Sarasota near Osprey, Florida , 1015 Crescent Street
Crescent Beach 1015 #4 is situated in Sarasota, 1.8 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art, and 18 km from The John an...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool
  • Air conditioning

Superb 10 Reviews 9.5

from $255.64 Show details »

Crescent Beach 1015 #2 in Sarasota, USA

Crescent Beach 1015 #2

Holiday home in Sarasota near Osprey, Florida , 1015 Crescent Street
Crescent Beach 1015 #2 is located in Sarasota, 1.8 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art, as well as 18 km from The J...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool
  • Air conditioning

Good 4 Reviews 7.7

from $198.63 Show details »

Crescent Beach 1011 #3 in Sarasota, USA

Crescent Beach 1011 #3

Holiday home in Sarasota near Osprey, Florida , 1011 Crescent Street
Located 1.8 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art and 18 km from The John and Mable Ringling Museum of Art, Crescent ...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool
  • Air conditioning

Fabulous 13 Reviews 8.7

from $258.23 Show details »

Crescent Beach 1011 #1 in Sarasota, USA

Crescent Beach 1011 #1

Holiday home in Sarasota near Osprey, Florida , 1011 Crescent Street
Crescent Beach 1011 #1 is located in Sarasota, 1.8 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art, as well as 18 km from The J...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool
  • TV

Very good 32 Reviews 8.5

from $281.96 Show details »

Coriander Cottage in Siesta Key, USA

Coriander Cottage

Holiday home in Siesta Key near Osprey, Florida , 1105 Point of Rocks Road
Featuring garden views, Coriander Cottage provides accommodation with a terrace and a patio, around 1.7 km from Turtle Beach.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 3 Reviews 9.3

from $289.00 Show details »

Wild Coffee in Siesta Key, USA

Wild Coffee

Holiday home in Siesta Key near Osprey, Florida , 1105 Point of Rocks Rd
Wild Coffee has a patio and is set in Siesta Key, within just 300 metres of Crescent Beach and 1.7 km of Turtle Beach.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 3 Reviews 9.7

from $319.00 Show details »

Wild Lime Cottage in Siesta Key, USA

Wild Lime Cottage

Holiday home in Siesta Key near Osprey, Florida , 1105 Point Of Rocks Rd
Boasting garden views, Wild Lime Cottage offers accommodation with barbecue facilities and a patio, around 1.7 km from Turtle Beach.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 3 Reviews 8.7

from $319.00 Show details »

Mulberry Cottage in Siesta Key, USA

Mulberry Cottage

Holiday home in Siesta Key near Osprey, Florida , 1105 Point of Rocks Rd
Featuring garden views, Mulberry Cottage provides accommodation with barbecue facilities and a patio, around 1.7 km from Turtle Beach.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Good 4 Reviews 7.7

from $319.00 Show details »

Fiddle Fig Cottage in Siesta Key, USA

Fiddle Fig Cottage

Holiday home in Siesta Key near Osprey, Florida , 1105 Point of Rocks Rd.
Located in Siesta Key and only 300 metres from Crescent Beach, Fiddle Fig Cottage provides accommodation with pool views, free WiFi and free private p...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Pleasant 5 Reviews 6.8

from $319.00 Show details »

Buttonwood Cottage in Siesta Key, USA

Buttonwood Cottage

Holiday home in Siesta Key near Osprey, Florida , 1105 Point Of Rocks Rd
Set in Siesta Key, 300 metres from Crescent Beach and 1.7 km from Turtle Beach, Buttonwood Cottage offers accommodation with free WiFi, air conditioni...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Bad 2 Reviews 1.0

from $379.00 Show details »

Point of Rocks Retreat in Sarasota, USA

Point of Rocks Retreat

Holiday home in Sarasota near Osprey, Florida
Located in Sarasota, 300 metres from Crescent Beach and 1.8 km from Turtle Beach, Point of Rocks Retreat offers free WiFi, a shared lounge and air con...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $291.29 Show details »

Vista Hermosa Steps to the Heated Pool in Sarasota, USA

Vista Hermosa Steps to the Heated Pool

Holiday home in Sarasota near Osprey, Florida
Vista Hermosa Steps to the Heated Pool is set in Sarasota, 1.8 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art, as well as 18 k...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $154.79 Show details »

Vista Hermosa 3rd Floor - Elevator in Sarasota, USA

Vista Hermosa 3rd Floor - Elevator

Holiday home in Sarasota near Osprey, Florida
Set 1.8 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art and 18 km from The John and Mable Ringling Museum of Art, Vista Hermosa...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $413.53 Show details »

Beach Club Cute Cottage in C Bldg in Sarasota, USA

Beach Club Cute Cottage in C Bldg

Holiday home in Sarasota near Osprey, Florida
Beach Club Cute Cottage in C Bldg is located in Sarasota, 2 km from Turtle Beach, 18 km from John and Mable Ringling Museum of Art, as well as 18 km f...
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $214.63 Show details »

Sun and Sea in Siesta Key, USA

Sun and Sea

Villa in Siesta Key near Osprey, Florida , 1135 Sun N Sea Drive Unit 1 & 2
Featuring free bikes, an outdoor swimming pool, and a garden, Sun and Sea by Beachside Management offers accommodation in Siesta Key with free WiFi an...
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 36 Reviews 8.7

from $331.71 Show details »

House of Sun Siesta Key Crescent Beach in Sarasota, USA

House of Sun Siesta Key Crescent Beach

Holiday home in Sarasota near Osprey, Florida
House of Sun Siesta Key Crescent Beach is a beachfront property set in Sarasota, 2.3 km from Turtle Beach and 17 km from John and Mable Ringling Museu...
  • Parking
  • Swimming pool
  • Swimming Pool

Fabulous 6 Reviews 8.8

from $431.89 Show details »

Lilac Mid-Century Pool Home in Sarasota, USA

Lilac Mid-Century Pool Home

Holiday home in Sarasota near Osprey, Florida
Set in Sarasota, Lilac Mid-Century Pool Home offers accommodation with a private pool.
  • Parking

no reviews

from $370.77 Show details »

Fantastic Island House 1 mile to the beach with heated pool in Sarasota, USA

Fantastic Island House 1 mile to the bea...

Holiday home in Sarasota near Osprey, Florida , 1770 Dawn Street
Situated in Sarasota, 1770 Dawn Street offers a shared outdoor pool and barbecue.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 10 Reviews 8.4

from $247.04 Show details »

Rowena House 2bd Den 2bth Heated Pool Near Siesta Key in Sarasota, USA

Rowena House 2bd Den 2bth Heated Pool Ne...

Holiday home in Sarasota near Osprey, Florida , 3320 Rowena Street
Boasting an outdoor swimming pool, a garden, and a terrace, Rowena House 2bd Den 2bth Heated Pool Near Siesta Key features accommodation in Sarasota w...
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

no reviews

from $255.77 Show details »

Heated Pool Home - Perfect Location - Walk to Beach, Restaurants and More! in Sarasota, USA

Heated Pool Home - Perfect Location - Wa...

Holiday home in Sarasota near Osprey, Florida , Beechwood Avenue
Boasting a private pool and garden views, Heated Pool Home - Perfect Location - Walk to Beach, Restaurants and More! is situated in Sarasota.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 1 Reviews 9.0

from $389.14 Show details »

Walk To Siesta Beach, Restaurants, Shopping & More! in Sarasota, USA

Walk To Siesta Beach, Restaurants, Shopp...

Holiday home in Sarasota near Osprey, Florida , 1641 Redwood Street
Walk To Siesta Beach, Restaurants, Shopping & More! is set in Sarasota, 16 km from John and Mable Ringling Museum of Art, 16 km from The John and Mabl...
  • Parking
  • Pets allowed

Superb 7 Reviews 9.3

from $134.99 Show details »

Walk to Beach, Restaurants, Shopping/Hot Tub! in Sarasota, USA

Walk to Beach, Restaurants, Shopping/Hot...

Holiday home in Sarasota near Osprey, Florida , 1641 Redwood Street
Featuring a spa bath, Walk to Beach, Restaurants, Shopping/Hot Tub! is set in Sarasota.
  • Parking
  • Pets allowed

no reviews

from $300.35 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