Search Condos Rentals in Osprey from CA $108

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Osprey Condo Rentals

Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
The price is CA $221
CA $297 total
includes taxes & fees
Aug 7 - Aug 8
Captiva Beach Resort
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (426)
"Everything was great. Great people to work with."
Venice Beach Villas
Cozy condo in charming Sarasota Siesta key with boat dock
Terrace/patio

Cozy condo in charming Sarasota Siesta key with boat dock

10.0 out of 10, Exceptional, (2)
"Amazing getaway! The location by the water was perfect for relaxing by boat. Cozy and well-equipped, we loved every moment. Highly recommend for a peaceful, scenic retreat."
Cozy condo in charming Sarasota Siesta key with boat dock
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, (21)
"Great view and nice place for a short stay. "
The price is CA $331
CA $637 total
includes taxes & fees
Aug 10 - Aug 11
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Palm Bay Club Private Balcony Beach Side
Pool

Palm Bay Club Private Balcony Beach Side

2.0 star property
8.8 out of 10, Excellent, (13)
"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
Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
9.8 out of 10, Exceptional, (9)
"Wonderful place to stay, quiet, close to the beach and wonderful restaurants within walking distance! Highly recommend!!!"
The price is CA $108
CA $741 total
includes taxes & fees
Aug 11 - Aug 12
Chadwick Cove Resort & Marina
Spectacular Beach View! Right on Beach! Amazing views!!
On the beach, sun loungers

Spectacular Beach View! Right on Beach! Amazing views!!

9.8 out of 10, Exceptional, (143)
"I really appreciated the owner and her interest in making sure everything was perfect during our stay! She was awesome!"
Spectacular Beach View! Right on Beach! Amazing views!!
Paradise 🏝Beach heaven 🌞condo 🦩<br>
Beach nearby, sun loungers, beach towels

Paradise 🏝Beach heaven 🌞condo 🦩<br>

9.6 out of 10, Exceptional, (47)
"very convenient to shopping and touring the Englewood/ Venice/Punta Gorda area"
Paradise 🏝Beach heaven 🌞condo 🦩<br>
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, (156)
"We could not have been happier with this location and its proximity to the beach and the pools. It was also close to great restaurants by locals who proudly serve great food!! "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
Beach nearby, beach umbrellas

2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

9.2 out of 10, Wonderful, (68)
"Nice location lots of hurricane damage"
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
Amazing Condo! Restored from Hurricane!
On the beach, sun loungers

Amazing Condo! Restored from Hurricane!

9.8 out of 10, Exceptional, (159)
"Quiet area with excellent beach access! Thank you"
Amazing Condo! Restored from Hurricane!
5 Minutes from Siesta Key!
Beach nearby, sun loungers, beach towels

5 Minutes from Siesta Key!

9.6 out of 10, Exceptional, (33)
"Unit was clean, great location and comfortable. Communication was great. Would stay again. "
5 Minutes from Siesta Key!
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 CA $391
CA $638 total
includes taxes & fees
Aug 11 - Aug 12
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
PARADISE ! 2 bedroom 2 bathroom with incredible views
A heated pool

PARADISE ! 2 bedroom 2 bathroom with incredible views

9.8 out of 10, Exceptional, (155)
"Beautiful Condo as listed with beautiful views. You can watch the sunrise right from your window or walk outside to the pool area. Karin was great communicating information needed prior to check in, or anytime if needed. Would def stay here again. "
PARADISE ! 2 bedroom 2 bathroom with incredible views
Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
Fridge, microwave, oven, stovetop

Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”

10.0 out of 10, Exceptional, (56)
"Awesome! The view of the ocean was well appreciated from the balcony in the evenings. Beautiful! Thanks again for your hospitality."
Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Beach nearby, sun loungers, beach towels

Vacation delight! Cozy condo just steps from the beach and St. Armands circle.

10.0 out of 10, Exceptional, (147)
"Property was well located, clean, and very well equipped. Would definitely stay here again! "
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Breathtaking Beach Front Property Ground Floor Condo
On the beach

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (143)
"Fantastic beach and accommodations. Everyone we met were so nice and friendly. Best sunsets on the gulf!!!"
Breathtaking Beach Front Property Ground Floor Condo
#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, (63)
"Perfect for what we wanted. Spent most of our time at the beach. They haveva dock in the back. Great for your coffee in the mornings, or kids to fish. Walkable to shops dunner,dinnet"
#1 Siesta Key Beach -Super Clean -2 Level Townhouse -2Br/2.5 Bth- 5 Star- 1400sf
Prime Beachfront with Views, Views, Views!
Property grounds

Prime Beachfront with Views, Views, Views!

9.6 out of 10, Exceptional, (82)
"The condo was clean, nicely decorated, spacious and very comfortable! It was steps from the beach and pool! The beach is absolutely beautiful! The pool was very nice! We would definitely stay here again! The beds are very comfortable and having two full bathrooms was so nice! We had a great week! "
Prime Beachfront with Views, Views, Views!
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)
"A beautiful view with amazing comfort in the condo! I can’t wait to come back!❤️😎"
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
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

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Booked at the last minute. Staff was friendly, and kind. Room was spacious and clean as was the hotel. Loved the welcome gift cookies "
Mary 1-night trip
Posted 10 hours ago
DoubleTree by Hilton Sarasota Bradenton Airport