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
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

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

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1082)
"Love Siesta Key"
The price is AED 756
AED 979 total
includes taxes & fees
20 Apr - 21 Apr
Captiva Beach Resort

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (405)
"Be careful when booking on expedia. I included my wife and I, and our two 4yos, and it still let me a book a studio with only a queen bed which said it only sleeps two, but i obviously overlooked it because i assumed it wouldnt let me book a room that only sleep two when we have four of us."
Venice Beach Villas

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (5)
"Chadwick Cove was recently renovated. The interior is cozy, clean and you have everything you need in the condo. Breakfast in the balcony to watch the sunrise at the bay was a plus."
The price is AED 468
AED 2,177 total
includes taxes & fees
28 Apr - 29 Apr
Chadwick Cove Resort & Marina

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

8.8 out of 10, Excellent, (5)
"Older building and units, but the location is great. Grocery store only a mile away. Right on the beach, so can just grab the room key and get on the beach. Kitchen had the basics. Balcony on the beach was the best part, we were out there a lot. "
The price is AED 882
AED 1,674 total
includes taxes & fees
23 Apr - 24 Apr
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

Bay View Condo, Walking Distance to Beach

9.4 out of 10, Exceptional, (35)
"The property was beautiful and we loved the dock. It was further to beach access than we expected, but it wasnt too bad. We'll definitely be back!"
Bay View Condo, Walking Distance to Beach

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

9.4 out of 10, Exceptional, (94)
"Overall it was good"
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

9.6 out of 10, Exceptional, (148)
"This was the perfect location in siesta key. We were right on the beach and enjoyed walking on the shore each day. The staff was super friendly and helpful and the grounds were clean. We are coming back next year and we’ve booked a 2-bedroom place so that we can bring family and friends. "
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

9.8 out of 10, Exceptional, (78)
" We had stayed in a different unit in the building the prior year and had found the location and close proximity to the beach to be ideal so we were excited to find this property last fall. But then the hurricane happened and changed it all. So many rentals were being canceled, beaches destroyed and we weren’t certain we still had a place to stay. But our host, Lisa, pulled it all together somehow and we were able to be the first to stay in her renovated condo. Decor is charming. Colors are...
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

9.6 out of 10, Exceptional, (5)
"The property was charming. Great access to the beach and many restaurants. "
The price is AED 845
AED 1,591 total
includes taxes & fees
1 May - 2 May
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway

9.6 out of 10, Exceptional, (54)
"The location was great. The rooms were clean. The management company was responsive for a small issue we had (needed tissues)"
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway

Welcome to Siesta Dreams at Casa Mar!!

9.8 out of 10, Exceptional, (47)
"Excellent! Perfect! Fun!"
Welcome to Siesta Dreams at Casa Mar!!

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

9.2 out of 10, Wonderful, (57)
"This Siesta Key condo is very cute and clean! We really enjoyed our time relaxing by the pool. The beach was quite a walk for my elderly mother, but they had a lot of other transportation options (Frog Hop was so easy!) nearby. "
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

Fun-n-Sun StepsFromWorld Famous Siesta Beach Spacious 2+2 Condo,pool,garage,wifi

9.8 out of 10, Exceptional, (142)
"This house was clean and greatly located. Close to beach and restaurants. Anything you need for the beach is provided so no need to pack all of that stuff. "
Fun-n-Sun StepsFromWorld Famous Siesta Beach Spacious 2+2 Condo,pool,garage,wifi

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

9.4 out of 10, Exceptional, (15)
"It was a magical trip and we’ve already booked for next year!!!"
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club

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

9.8 out of 10, Exceptional, (50)
"Excellent location in a quaint neighborhood allowing for easy access to attractions, dining, shopping and the beach. "
The price is AED 275
AED 551 total
includes taxes & fees
1 May - 2 May
Sapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8.0 out of 10, Very Good, (5)
"Property was exactly as described. Comfortable, on the beach with easy access to shopping, groceries and restaurants. We’ll definitely be back! "
The price is AED 882
AED 1,636 total
includes taxes & fees
30 Apr - 1 May
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

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

10.0 out of 10, Exceptional, (78)
"We absolutely loved everything about this beach property! We had a perfect stay and definitely plan on returning "
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

9.8 out of 10, Exceptional, (118)
"The location of this condo is perfect. Michelle is very responsive and easy to work with. The condo had all of the items we needed and more. "
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!

9.6 out of 10, Exceptional, (90)
"We stayed late-Dec / early-Jan and had an absolutely amazing trip. The condo is exactly as advertised and was perfectly clean upon arrival. Check-in was very easy and instructions were very clear. The master king bed is very comfortable; one of the best my wife and I have slept in staying at a VRBO. The kids room is nice and connects to the 2nd bathroom. Views from both bedrooms are fantastic. Our girls are 4.5 and 1.5 and the unit was perfect for them. Kitchen has everything you need for all...
7th-Floor Oceanfront Palm Beach Club Condo | Stunning Views | Heated Pool | Prime Location!

Beach View Condo-Quiet & Secluded Private Beach

10.0 out of 10, Exceptional, (29)
"Beautiful property that was extremely clean and comfortable. We have stayed in longboat before, it this location was the best of the best "
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

Other property types in Osprey

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

3.5 star property
9.4 out of 10, Exceptional, (4627)
"Nice place and clean! Staff was very friendly and helpful. "
The price is AED 590
AED 750 total
includes taxes & fees
20 Apr - 21 Apr
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2113)
"Location is great..Crescent Beach within a reasonable walking distance. The suite was clean and comfortable. The staff were very helpful. The pool is a nice feature. Extra amenities like beach towels, chairs , umbrellas, grills to cook on were nice. Only negative was that the street is busy so the traffic is a little loud by the pool or if you are sitting outside your room. Inside it is not a bother.This is my second time here... I would come back."
The price is AED 606
AED 684 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 275 to AED 885 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 9.4. 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.