Minimap with link to location map
Filters
Price
Rating
Distance from Center
Rating (according to Stars)
Facilities

Check availability






Holiday homes in Osprey (Page 5)

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)
Elegant Venice Home with View - Walk to Beach! in Venice, USA

Elegant Venice Home with View - Walk to...

Holiday home in Venice near Osprey, Florida
Featuring a spa bath, Elegant Venice Home with View - Walk to Beach! is located in Venice.
  • Parking

Very good 2 Reviews 8.5

from $419.33 Show details »

Newly Fully Updated and Modern, Short Walk to BEACH in Siesta Key, USA

Newly Fully Updated and Modern, Short Wa...

Holiday home in Siesta Key near Osprey, Florida , 632 Calle De Otono
Newly Fully Updated and Modern, Short Walk to BEACH is set in Siesta Key, 1.2 km from Crescent Beach, 17 km from John and Mable Ringling Museum of Art...
  • Parking

Exceptional 7 Reviews 9.7

from $252.25 Show details »

Walk to Beach, Updated Condo, Private Patio and Grill in Siesta Key, USA

Walk to Beach, Updated Condo, Private Pa...

Holiday home in Siesta Key near Osprey, Florida , 632 Calle De Otono
Located 1.1 km from Crescent Beach, 17 km from John and Mable Ringling Museum of Art and 17 km from The John and Mable Ringling Museum of Art, Walk to...
  • Parking

Fabulous 9 Reviews 8.9

from $253.47 Show details »

Spacious Updated Condo Just 2 Blocks to Siesta Key Beach in Siesta Key, USA

Spacious Updated Condo Just 2 Blocks to...

Holiday home in Siesta Key near Osprey, Florida , 632 Calle De Otono
Set in Siesta Key, 400 metres from Siesta Key Beach and 1.1 km from Crescent Beach, Spacious Updated Condo Just 2 Blocks to Siesta Key Beach offers ai...
  • Parking

Exceptional 8 Reviews 9.8

from $362.80 Show details »

NEW Location, Location, Location! On the BEACH, Walk to VILLAGE in Sarasota, USA

NEW Location, Location, Location! On the...

Holiday home in Sarasota near Osprey, Florida , 524 Beach Road
Featuring a childrens playground and an ATM, NEW Location, Location, Location!
  • Parking
  • Fitness centre
  • Spa and wellness centre

Very good 1 Reviews 8.0

from $496.29 Show details »

Oasis with 2 Stand-Alone Casitas and Outdoor Bath in Sarasota, USA

Oasis with 2 Stand-Alone Casitas and Out...

Holiday home in Sarasota near Osprey, Florida
Situated 14 km from John and Mable Ringling Museum of Art, 14 km from The John and Mable Ringling Museum of Art and 8.2 km from Sarasota Opera, Oasis ...
  • Parking

no reviews

from $118.00 Show details »

Chic Sarasota Cottage Near Beaches and Downtown! in Sarasota, USA

Chic Sarasota Cottage Near Beaches and D...

Holiday home in Sarasota near Osprey, Florida
Located in Sarasota, 15 km from John and Mable Ringling Museum of Art, 15 km from The John and Mable Ringling Museum of Art and 9.2 km from Sarasota O...
  • Parking
  • Internet facilities
  • Hairdryer
  • Iron
  • Refrigerator

Superb 4 Reviews 9.5

from $224.33 Show details »

Sarasota Getaway with Private Pool and Backyard Oasis! in Sarasota, USA

Sarasota Getaway with Private Pool and B...

Holiday home in Sarasota near Osprey, Florida
Within 14 km of John and Mable Ringling Museum of Art and 14 km of The John and Mable Ringling Museum of Art, Sarasota Home with Pool about 5 Miles to...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 2 Reviews 10.0

from $378.71 Show details »

Steps to #1 Beach in America Siesta Beach! in Siesta Key, USA

Steps to #1 Beach in America Siesta Beac...

Holiday home in Siesta Key near Osprey, Florida , 5306 Calle De La Siesta
Set in Siesta Key in the Florida region, Steps to #1 Beach in America Siesta Beach! has a balcony and garden views.
  • Parking
  • Family rooms

Exceptional 3 Reviews 10.0

from $216.28 Show details »

Walk to the Beach or Village in minutes! in Siesta Key, USA

Walk to the Beach or Village in minutes!

Holiday home in Siesta Key near Osprey, Florida , 5304 Calle De La Siesta
Set 300 metres from Siesta Key Beach, 1.8 km from Crescent Beach and 16 km from John and Mable Ringling Museum of Art, Walk to the Beach or Village in...
  • Parking
  • Family rooms
  • Air conditioning
  • Washing machine
  • Private bathroom

Fabulous 1 Reviews 9.0

from $260.85 Show details »

Ideal Beach Cottage Steps to Siesta Beach and Village Shops and Restaurants in Siesta Key, USA

Ideal Beach Cottage Steps to Siesta Beac...

Holiday home in Siesta Key near Osprey, Florida , 303 Beach Road Unit #1
Located in Siesta Key in the Florida region, Ideal Beach Cottage Steps to Siesta Beach and Village Shops and Restaurants features a patio.
  • Parking

Disappointing 6 Reviews 4.5

from $197.28 Show details »

Charming Beach Cottage Steps to Siesta Beach and Village Shops and Restaurants in Sarasota, USA

Charming Beach Cottage Steps to Siesta B...

Holiday home in Sarasota near Osprey, Florida , 303 Beach Road Unit #2
Located in Sarasota in the Florida region, Charming Beach Cottage Steps to Siesta Beach and Village Shops and Restaurants has a patio.
  • Parking

Pleasant 16 Reviews 6.2

from $198.11 Show details »

Siesta Beach Cottage, Sleeps 6, Walk to Beach, Stores, & Restaurants in Siesta Key, USA

Siesta Beach Cottage, Sleeps 6, Walk to...

Holiday home in Siesta Key near Osprey, Florida , 303 Beach Road Unit #3
Situated in Siesta Key in the Florida region, Siesta Beach Cottage, Sleeps 6, Walk to Beach, Stores, & Restaurants features a patio.
  • Parking

Pleasant 26 Reviews 6.6

from $177.26 Show details »

Retreat Half-Mile to BeachandSiesta Key Village in Siesta Key, USA

Retreat Half-Mile to BeachandSiesta Key...

Holiday home in Siesta Key near Osprey, Florida
Located in Siesta Key, 1 km from Siesta Key Beach and 2.5 km from Crescent Beach, Retreat Half-Mile to Beach and Siesta Key Village provides accommoda...
  • Parking

Good 7 Reviews 7.7

from $208.67 Show details »

Sunkissed Pool Home in Siesta Key, USA

Sunkissed Pool Home

Holiday home in Siesta Key near Osprey, Florida
Set in Siesta Key, Sunkissed Pool Home offers a private pool.
  • Parking

no reviews

from $334.39 Show details »

Sarasota Architecture Home in Siesta Key, USA

Sarasota Architecture Home

Holiday home in Siesta Key near Osprey, Florida , 5153 Sandy Cove Ave
Located in Siesta Key, Sarasota Architecture Home provides a private pool.
  • Parking

no reviews

from $466.15 Show details »

Siesta Key Beach Resort and Suites in Sarasota, USA

Siesta Key Beach Resort and Suites

Villa in Sarasota near Osprey, Florida , 5311 Ocean Boulevard
Located just 1 minutes’ walk from the beach, this Siesta Key resort features a swimming pool.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Outdoor pool

Very good 1099 Reviews 8.3

from $234.90 Show details »

Avenida De Cortez 5210 in Siesta Key, USA

Avenida De Cortez 5210

Holiday home in Siesta Key near Osprey, Florida , 5210 Avenida De Cortez
Set in Siesta Key, Avenida De Cortez 5210 offers a private pool.
  • Parking
  • Fitness centre
  • Spa and wellness centre
  • Outdoor pool
  • Swimming pool

Exceptional 1 Reviews 10.0

from $381.77 Show details »

Siesta Avenida Townhome 5208 in Siesta Key, USA

Siesta Avenida Townhome 5208

Holiday home in Siesta Key near Osprey, Florida , 5208 Avenida De Cortez
Situated in Siesta Key, Siesta Avenida Townhome 5208 features accommodation with a private pool.
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 2 Reviews 10.0

from $324.00 Show details »

Canal 313 - Right in Siesta Key Village! in Siesta Key, USA

Canal 313 - Right in Siesta Key Village!

Holiday home in Siesta Key near Osprey, Florida
Located in Siesta Key, Canal 313 - Right in Siesta Key Village! provides accommodation with a private pool and free WiFi.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Very good 15 Reviews 8.6

from $240.35 Show details »

Canal 315 - Right in Siesta Key Village! in Siesta Key, USA

Canal 315 - Right in Siesta Key Village!

Holiday home in Siesta Key near Osprey, Florida , 315 Canal Road
Situated in Siesta Key, Canal 315 - Right in Siesta Key Village! features accommodation with a private pool and free WiFi.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Very good 7 Reviews 8.0

from $310.02 Show details »

Avenida Upper in Siesta Key, USA

Avenida Upper

Holiday home in Siesta Key near Osprey, Florida , 340 Avenida De Mayo, Siesta Key, FL 34242, USA
Situated in Siesta Key, 600 metres from Siesta Key Beach and 2.2 km from Crescent Beach, Avenida Upper offers free WiFi, a garden and air conditioning...
  • Swimming pool
  • Swimming Pool

Pleasant 1 Reviews 6.0

from $330.57 Show details »

Avenida Lower in Siesta Key, USA

Avenida Lower

Holiday home in Siesta Key near Osprey, Florida , 340 Avenida De Mayo Lower
Set in Siesta Key, 600 metres from Siesta Key Beach and 2.2 km from Crescent Beach, Avenida Lower offers free WiFi, a garden and air conditioning.

Good 7 Reviews 7.9

from $343.00 Show details »

Canal 309 - Right in Siesta Key Village! in Siesta Key, USA

Canal 309 - Right in Siesta Key Village!

Holiday home in Siesta Key near Osprey, Florida , 309 Canal Road
Set in Siesta Key, Canal 309 - Right in Siesta Key Village! offers a private pool and free WiFi.
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

Very good 7 Reviews 8.6

from $310.02 Show details »

Tropical Fruit Garden in Sarasota, USA

Tropical Fruit Garden

Holiday home in Sarasota near Osprey, Florida , 4001 Groveland Ave
Located in Sarasota 5 km from Siesta Key, this Florida Tropical Fruit Garden boasts a year-round, heated outdoor pool and barbecue.
  • Parking
  • Family rooms
  • Allergy-free room
  • Outdoor pool
  • Swimming pool

Superb 28 Reviews 9.1

from $169.00 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