Search Condo Rentals in Osprey

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 3607 Condo Rentals in Osprey with updated reviews, rates, and availability.

Captiva Beach Resort
Florida Family Single | Private kitchen | Fridge, microwave, coffee/tea maker, toaster

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1087)
"Close to beach and pool ."
The price is AED 700
AED 915 total
includes taxes & fees
1 May - 2 May
Captiva Beach Resort
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (406)
"Loved it. The owner is so friendly and he keeps the place clean and respectful. He offers a lot of amenities. "
Venice Beach Villas
Chadwick Cove Resort & Marina
Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (5)
"This was an excellent property to stay in. I will definitely rebook when I travel to Englewood, Fl. "
The price is AED 481
AED 2,191 total
includes taxes & fees
12 May - 13 May
Chadwick Cove Resort & Marina
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
On the beach

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

8.8 out of 10, Excellent, (6)
The price is AED 882
AED 1,667 total
includes taxes & fees
3 May - 4 May
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Bay View Condo, Walking Distance to Beach
Beach nearby

Bay View Condo, Walking Distance to Beach

9.4 out of 10, Exceptional, (36)
"We enjoy the main level condo with a nice view of the water. The dock is great for fishing. "
Bay View Condo, Walking Distance to Beach
Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!
A heated pool

Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!

9.4 out of 10, Exceptional, (94)
"Excellent space"
Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
On the beach, sun loungers

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

9.6 out of 10, Exceptional, (149)
"Excellent location right on the beach! Quiet and relaxing. The property provides beach loungers and you can bring your own umbrella or rent one for the day or your stay. Our unit was on the 2nd floor and liked that there were 2 Queen Beds in the one bedroom. Furnishings were a little worn around the edges, but was comfortable and had all we needed for cooking and even a cooler for the beach, "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach
Beach nearby, sun loungers, beach towels

Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (80)
"Had a great trip! Clean, quiet & great location!"
Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
On the beach

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

9.8 out of 10, Exceptional, (7)
The price is AED 845
AED 1,573 total
includes taxes & fees
4 May - 5 May
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway
On the beach

Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway

9.6 out of 10, Exceptional, (55)
"Great!"
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway
Welcome to Siesta Dreams at Casa Mar!!
On the beach

Welcome to Siesta Dreams at Casa Mar!!

9.8 out of 10, Exceptional, (48)
"A good stay overall."
Welcome to Siesta Dreams at Casa Mar!!
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
Beach nearby, sun loungers, beach towels

Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

9.2 out of 10, Wonderful, (61)
"This was a good condo style property on the key. Good location. Great owner with great communication. I did not have the opportunity to ask about the water heater regarding showers. The shower would get luke warm, but we did get ready at the same time. I would definitely rent this property again. "
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
See July 4 Fireworks across the street on #1 Siesta Beach Spacious 2+2Condo,pool
Beach nearby, sun loungers, beach umbrellas, beach towels

See July 4 Fireworks across the street on #1 Siesta Beach Spacious 2+2Condo,pool

9.8 out of 10, Exceptional, (144)
"2nd year in a row coming down to Siesta Key for Christmas and 2nd time staying at a property managed by Gail and H. They are attentive and thoughtful hosts and their properties are immaculate and exactly as advertised. We’re already booked to return in November!!"
See July 4 Fireworks across the street on #1 Siesta Beach Spacious 2+2Condo,pool
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Outdoor pool, a heated pool

Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club

9.4 out of 10, Exceptional, (16)
"The condo was beautiful, clean and well stocked. We had everything we needed for a Christmas beach vacation. "
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Terrace/patio

Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

9.8 out of 10, Exceptional, (50)
"We loved the style of this guest home. Beautifully tucked into a luscious leafy neighborhood! Very clean and close to Sarasota sights to see."
The price is AED 275
AED 551 total
includes taxes & fees
5 May - 6 May
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Outdoor dining

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8.6 out of 10, Excellent, (8)
The price is AED 882
AED 1,629 total
includes taxes & fees
7 May - 8 May
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Beach nearby, sun loungers, beach towels

DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

10.0 out of 10, Exceptional, (82)
"Love stay at this right on the beach condo"
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now
On the beach, sun loungers, beach towels

Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now

9.8 out of 10, Exceptional, (119)
"We had a wonderful stay in Siesta Key and the condo was just perfect in every way!"
Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now
7th-Floor Oceanfront Palm Beach Club Condo | Stunning Views | Heated Pool | Prime Location!
On the beach

7th-Floor Oceanfront Palm Beach Club Condo | Stunning Views | Heated Pool | Prime Location!

9.6 out of 10, Exceptional, (91)
"Although the weather wasn't as warm as we hoped, the beach and the unit were still spectacular. Our group had an amazing time in Siesta Keys and would love to have stayed longer and will definitely plan a return trip."
7th-Floor Oceanfront Palm Beach Club Condo | Stunning Views | Heated Pool | Prime Location!
Beach View Condo-Quiet & Secluded Private Beach
Beach nearby

Beach View Condo-Quiet & Secluded Private Beach

10.0 out of 10, Exceptional, (30)
"Great access to a beautiful beach!"
Beach View Condo-Quiet & Secluded Private Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Osprey
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Osprey

Huge Pool, Close to Beaches, Restaurants, Shopping & More!
Smart TV, foosball, books

Huge Pool, Close to Beaches, Restaurants, Shopping & More!

9.6 out of 10, Exceptional, (22)
"What a wonderful place to relax! Will definitely recommend to family and friends and even come back to stay!"
Huge Pool, Close to Beaches, Restaurants, Shopping & More!
Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4642)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is AED 538
AED 691 total
includes taxes & fees
27 May - 28 May
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2120)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
The price is AED 587
AED 664 total
includes taxes & fees
1 May - 2 May
Hibiscus Suites - Gateway to Siesta Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from AED 481 to AED 882 per night. These stays provide loads of space for your whole crew at a price that’s friendly on the pocket. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Osprey?
Osprey has multiple condos with a total average guest review rating of 9.3. Venice Beach Villas is one highly recommended option. Guests of this 3-star condo will have use of a barbecue grill and an electric car charging station. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is also a winner with travelers to the area. This 3-star property has a deck and a lanai.
How many condos are there in Osprey?
Work out your vacation dates and then pick from 3607 condos in Osprey. For an official business trip, a couples’ getaway or anything in between, Expedia will help you find the perfect place in a few quick clicks.