We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Osprey

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    S$146 Average
    |||
    |||
    S$0S$1,000+
    Suitability
    Suitability
    More filters
    Osprey is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    All 25 Rentals in Osprey
    Sort by:
    Default
    Osprey
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Welcome to the Paradise1 / 17
    (1)Excellent
    Osprey
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (2)Very good
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 December 2017
    We had a great stay for the month and plan to come again. Great location midway between our favorite beaches, Caspersen, Casey Key and Siesta Key. Very private lanai and pool...
    See all reviews
    About this property
    Absolutely the best value for your vacation dollar in the Sarasota-Osprey-Nokomis-Venice area ! This newly renovated pet friendly paradise is a single family 3 br - 2 bath home with heated pool that has it all. Large, extremely well equipped kitchen with granite countertops, double convection...
    View all property information
    Location Information
    Osprey, Florida 34229
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dear Renter, I am Beya, the owner and I'm offering authentic villas in the natural environment on Palmer Ranch. The villa is a spacious house with stunning garden with palm and pine trees. The location is just perfect, Mall, restaurants, and park are located just minutes drive, sparkling Siesta Key...
    View all property information
    Location Information
    Osprey, Florida 34238
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key1 / 15
    (2)Excellent
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    The location is amazing! The condo was super clean and very family friendly. I loved the community with multiple pools and the awesome clubhouse. It was just a short drive or...
    Reviewed 25 May 2018
    There was not a single unmet need the entire week. This unit is clean, comfortable, and serene. The kitchen has everything, so we cooked a lot. From the beach towels, cooler...
    See all reviews
    About this property
    Stoneybrook Golf & Country Club is a gated community on Palmer Ranch with a fully renovated clubhouse with fine and casual dining, close proximity to Siesta Key's world-famous beaches, shops, restaurants, and Sarasota's active arts communities. This unit is a ground-floor end/corner unit with extra...
    View all property information
    Location Information
    Osprey, Florida 34238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Osprey
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Idyllic beachfront home located on exclusive, unique Casey Key in Sarasota, Florida. Set in lush tropical greenery including 61 palm trees, sea grapes, and Hibiscus plants, just a few backyard steps to a white sand beach and spectacular sunsets on the Gulf of Mexico. Walk to historic Casey Key...
    View all property information
    Location Information
    Osprey, Florida 34229
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunshine awaits at this 3BR/2BA Sarasota home for six guests, featuring brand new updates and tranquil landscaping. Spend leisurely afternoons on your private patio with BBQ grill, and dine al fresco in your own backyard. Or visit downtown Sarasota and treat yourself to upscale shopping and...
    View all property information
    Location Information
    Osprey, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Osprey
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Cove Yacht & Racquet Club is the most scenic, relaxing vacation spot on Siesta Key, a barrier island separating the Gulf of Mexico from Sarasota Bay. Located at the quiet end of Siesta Key, across from Turtle Beach, every unit has a direct water view. Nearby Siesta Beach was voted The Best...
    View all property information
    Location Information
    Osprey, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Osprey
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Begin your sunkissed adventures at this 2-bedroom, 1-bathroom vacation rental condo that sleeps 4 in Siesta Key. This coastal condo boasts all the amenities of home with the luxuries of an upscale resort. Spend your days lounging around the heated community pool or take a short stroll to nearby...
    View all property information
    Location Information
    Osprey, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Osprey rentals sent straight to your email!
    Get the List
    The following rentals are within 10 kilometres of Osprey.
    Sarasota Siesta Key Beaches1 / 21
    (1)Excellent
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    Awesome house for vacation in Sarasota. House was very clean and has very nice decoration.There is beach umbrellas and beach chairs in the house,toys for kids to play in the...
    See all reviews
    About this property
    Rarely rent able Gulf Gate home with 2 bedrooms and 2 bathrooms. Completely redone inside. Incredible kitchen with designer Viking appliances, granite counters and wood cabinetry. Bamboo hardwood floors throughout. Amazing Master Bathroom with walk through shower, designer sinks, and lots of room....
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    4/3 Pool home 4 miles from Siesta Key Beach1 / 24
    (1)Excellent
    Gulf Gate Branch
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 January 2018
    This was an amazing place and we couldn't have been happier with our selection. Having a screened in pool attached to the house allowed us easy access everywhere without going...
    See all reviews
    About this property
    U-shaped home surrounding a private pool in the center. 4 bedrooms, living and dining area overlook pool. 40' of glass doors make this true indoor/outdoor living. House sits on a corner lot with 2 driveways. There is room for 2 cars in the rear driveway. House also has a washer/dryer. Split plan...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34233
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in comfort at Sea Winds! The unit offers a king bed and sleeper sofa, open patio space and a garden view, perfect for enjoying an outdoor meal. Take a dip in the community pool or shop the neighboring plazas. Beach accesses are 2 blocks in either direction, just a short walk.. Wireless...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Village des Pins! We offer you a lovely 2 bedroom, 2 bath, one car garage, single story villa surrounded by beautiful Florida Palms and other luscious greenery on the south side of Sarasota. This community has a clubhouse with many amenities, including a two tennis courts (lighted),...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    LUX CONDOs near beautiful, sparkling Siesta Key Beach.1 / 27
    (1)Excellent
    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2017
    The location is great. Really close to the beach. The host is very friendly and helpful. We enjoyed our vacation.
    See all reviews
    About this property
    Dear Renter, I am Beya, the owner with more a decade experience in the vacation rental field. I have been offering authentic condos in the beautiful natural area of the Vintage Grand community. I would be happy to host you in one of my condos.I have down and upstairs floor condos with lake-view or...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34238
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing 2 bedrooms, 2 bathroom, with private backyard in a quiet neighborhood. This bright and fully remodeled home is tastefully decorated and well stocked. Conveniently located close walk to Publix and Walmart. Restaurants, cafeterias, spas, beauty salons, bars are around downtown area and only...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34233
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Patio
    • Washer
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    I loved my stay at this family-friendly rental. Perfect location - a quick drive to the beach, Siesta Village, and downtown Sarasota! The home had everything we could possibly...
    Reviewed 6 days ago
    The house was very nice and was in a wonderful location. Everything was provided for a perfect stay. We would love to stay here again in the future!
    See all reviews
    About this property
    This spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St Armand's Circle with tons of shops and restaurants! The Master bedroom has a king-sized bed...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Hot Tub
    • Patio
    • Balcony
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are a 2 bedroom 2 bathroom fully furnished and equipped villa located in popular Village des Pins, Sarasota. 25 acre landscapped community. Just a short drive away from the world famous Siesta Key Beach with its unique white powdery sand. Sarasota Square Mall and the AMC 12 I-Max cinema are...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34238
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedrooms, 2 Bathrooms, Sleeps 4 1/2 mile from The Gulf Of Mexico WIFI with HDTV in the living area Pets allowed with permission and pet deposit Absolutely no pets allowed in the pool area Short walk to the beach Private condo 8 units on the complex Looking for a tropical winter get-away or...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34231
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Gulf Gate Branch
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In-law apartment private & comfy, 1 bedroom(queen bed), 1 bathroom, 2 chairs, Small fridge, Microwave, TV Cable, Internet, Parking, quiet and safe neighborhood. This is a Private small place in a residential family home, just 10 minutes driving to the beautiful beaches, Siesta key, lido key, tutle...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34233
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Hot Tub
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW seasonal rental property available in Sarasota Gulf Gate neighborhood with close proximity to Siesta Key Beach, shopping, restaurants, just about everything ! 2 bedrooms, 3 NEW queen size beds, 2 baths, large NEW screened lanai includng a pool and integrated spa/hot tub! 1 car garage with new...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only 8 min. to the #1 Beach in the USA 'Siesta Key Beach'!! Our 'SUPER CLEAN' large 3 bedroom / 2 bathroom condo in a beautiful gated complex. This spacious split plan offers a master bedroom with a walk-in closet, central living room, kitchen, dining room room and two bedrooms on seperate wings...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Gulf Gate Branch
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfy Efficiency( small studio apartment),1 bedroom, 1 bed(queen), 1 sofa, 1 bath, kitchen fully furnished, Internet WIFI, Cable TV, parking. Air conditioning window unit. Nice place centrally located, just a few minutes driving to the beaches, Siesta key, Lido key, St. Armands Circle, Marina Jack...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34233
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for families and groups of friends, this sunny home has everything (including a scenic pond!) you need to enjoy some Florida sunshine in Sarasota. From natural beauty to nearby shops, restaurants, and beaches, you have plenty of ways to make the most of your Florida getaway. Nestled in a...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Balcony
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our cottage has been recently remodeled. The cottage has a full kitchen with all the amenities of home. A large front porch where you can enjoy balmy florida weather while you are bbq your fresh catch. We are located about 3 miles to Siesta Key. Beach bike and beach chairs are included in our...
    View all property information
    Location Information
    Gulf Gate Branch, Florida 34231
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in