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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Condo Rentals in Osprey

Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1123)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
Captiva Beach Resort
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (429)
"Easy walk or bike ride to beach. Property has plenty of bikes to borrow with locks. Overall just super place that I’ll stay again. "
Venice Beach Villas
Take a Peek at a fabulous unit.
Property grounds

Take a Peek at a fabulous unit.

10.0 out of 10, Exceptional, (122)
"You can not get any closer to the beach than this. The view, the room and our property manager were all amazing. ZERO complaints. Can't wait to go back. "
The price is ￥32,929
￥72,689 total
includes taxes & fees
Sep 1 - Sep 2
Take a Peek at a fabulous unit.
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, (158)
"Security, beach access, nice unit!"
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
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

9.8 out of 10, Exceptional, (28)
"We stayed here to celebrate our anniversary and it was great. Highly recommended. "
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Smart TV, books

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (95)
"Lovely unit and the perfect location. Short walk to the beach and easy to get to the shopping/eating areas. "
The price is ￥25,097
￥62,393 total
includes taxes & fees
Sep 1 - Sep 2
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
On the beach, sun loungers, beach towels

DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!

9.8 out of 10, Exceptional, (59)
"Really nice property. So glad it survived the hurricane. Can’t wait to stay there again. "
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
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, (23)
"Great view and nice place for a short stay. "
The price is ￥35,266
￥68,247 total
includes taxes & fees
Aug 25 - Aug 26
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Sun loungers

*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

9.8 out of 10, Exceptional, (44)
"Will stay again! "
*Casa Bella* Waterfront View! 2BR, w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
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, (90)
"Had an awesome time, perfect place on the beach."
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,
Fridge, microwave, oven, stovetop

On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,

10.0 out of 10, Exceptional, (176)
"Beautiful condo, ocean view, nicely decorated with a beachy theme. Full of supplies, even shampo, we'll be back. "
On Siesta Key/Crescent Beach,View, pool, 2 Bed 2 Ba, plus pull out Queen,
Palm Bay Club Private Balcony Beach Side
Pool

Palm Bay Club Private Balcony Beach Side

2.0 star property
9.0 out of 10, Wonderful, (14)
"Nice location, clean place, great communication even when our family hit some bumps with our trip. Overall highly recommend and and plan to return. "
Palm Bay Club Private Balcony Beach Side
Prime Beachfront with Views, Views, Views!
Property grounds

Prime Beachfront with Views, Views, Views!

9.6 out of 10, Exceptional, (85)
"There is still some storm recovery in the garden suites area from last year's hurricanes, but the towers and beach are back to normal. Staff was super responsive."
Prime Beachfront with Views, Views, Views!
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
On the beach

Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC

6.6 out of 10, (7)
"Great location and beach access- pool is awesome! Unit doesn’t face the ocean, but it’s right there! Very low key- place is very clean. WiFi is spotty and would not be good if you are planning to work while staying- that is an island wide issue I believe- No stove, but has everything else a kitchen needs and a grill- we would come back! "
The price is ￥42,760
￥69,390 total
includes taxes & fees
Sep 3 - Sep 4
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
Paradise 🏝Beach heaven 🌞condo 🦩<br>
Beach nearby, sun loungers, beach towels

Paradise 🏝Beach heaven 🌞condo 🦩<br>

9.6 out of 10, Exceptional, (50)
"very convenient to shopping and touring the Englewood/ Venice/Punta Gorda area"
Paradise 🏝Beach heaven 🌞condo 🦩<br>
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Outdoor dining

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

9.0 out of 10, Wonderful, (17)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
The price is ￥33,796
￥61,700 total
includes taxes & fees
Aug 25 - Aug 26
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
On the beach

GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

9.8 out of 10, Exceptional, (103)
"Very good location excellent apartament "
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
On the beach, sun loungers, beach towels

Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

9.8 out of 10, Exceptional, (260)
"The facility was great"
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
Modern Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
Beach

Modern Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

9.8 out of 10, Exceptional, (179)
"Our location was perfect to IMG where our son was playing. Close to restaurants and easy to get to beach. Would stay there again!"
The price is ￥15,429
￥46,507 total
includes taxes & fees
Sep 5 - Sep 6
Modern Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
#1 Siesta Key Beach -Super Clean -2 Level Townhouse -2Br/2.5 Bth- 5 Star- 1400sf
Beach nearby

#1 Siesta Key Beach -Super Clean -2 Level Townhouse -2Br/2.5 Bth- 5 Star- 1400sf

9.6 out of 10, Exceptional, (64)
"Very nice property. The owner is very responsive to any issues. The only thing I wasn't a fan of is the ac cycling over and over through the night, but that was very minor. Would absolutely stay here again in the future. "
#1 Siesta Key Beach -Super Clean -2 Level Townhouse -2Br/2.5 Bth- 5 Star- 1400sf
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.
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Top Osprey Hotel Reviews

Ameniti Bay, BW Signature Collection

Ameniti Bay, BW Signature Collection

10/10 Excellent
"Great service and nice rooms with great showers "
alan 2-night trip
Posted 17 hours ago
Ameniti Bay, BW Signature Collection

Frequently asked questions

How much do condos in Osprey cost?
Condos in Osprey range from ￥15,429 to ￥42,760 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?
Choose from multiple condos in Osprey with a total average guest review rating of 9.3. Venice Beach Villas comes highly recommended if you're traveling with the whole crew or just want to stretch out. This 3-star condo also features therapeutic mineral springs and a barbecue grill. Walk To The Beach From Modern Condo Or Hop On A Bike To Siesta Village is another guest fave. It has a 3-star rating and amenities such as a deck and a lanai.
How many condos are there in Osprey?
Work out your vacation dates and then pick from 3739 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.