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.

Vacation rentals in Osprey, FL and nearby

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 418 Rentals in the Osprey Area
loading...
From
$161
Per Night
1 / 17
Payment Protection
Osprey
3 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Reviews (1) Make Enquiry
From
$1,354
Per Week
1 / 14
Payment Protection
Osprey
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
From
$56
Per Night
1 / 15
Osprey
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Also consider
January 2015  Now Available at Villa Grande!
2 Bedrooms, sleeps 6
$130 - $191 / night
1 Bed Siesta Key Vacation Condo Rental
1 Bedroom, sleeps 4
$113 / night
Charming Villa, Close to beach, "West of Trail"
2 Bedrooms, sleeps 5
$73 - $164 / night
Sea Crest on Siesta Key ..Vacation Rental Condo's
1 Bedroom, sleeps 4
$141 - $237 / night

The following rentals are within 15 kilometres of Osprey, Florida.

From
$188
Per Night
1 / 40
Payment Protection
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (5) Make Enquiry
From
$113
Per Night
1 / 18
Payment Protection
Nokomis
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 March 2013
We actually did not stay in this unit ( although we did go into it), we stayed at the 2 bedroom unit next door. The decor was old Florida with a touch of Hawaii, very chic yet...
See all reviews
From
$193
Per Night
1 / 25
Payment Protection
Siesta Key
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 26 August 2014
Our stay was from Aug 16th to 23rd with our 3 teens and 2 of their friends. We were thrilled to open the front door and discover a lovely and comfortable home! Very spacious...
See all reviews
From
$79
Per Night
1 / 11
Payment Protection
Nokomis
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 21 August 2014
We really enjoyed our stay and Colleen was great. She met us when we arrived and showed us around. From there on I only had to send her a text if there was anything I needed and...
See all reviews
From
$745
Per Night
1 / 40
Payment Protection
Venice
6 Bedrooms, 4 Bathrooms, Sleeps 16
Details Reviews (31) Make Enquiry
3 of 5 stars Reviewed 3 May 2014
This home was better than the so called Villas Mansion, also in Venice. Needs deep cleaning - more than the usual turn around between guests. Found three large but dead...
See all reviews
Get the List
From
$333
Per Night
1 / 24
Payment Protection
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 3 August 2014
We really enjoyed staying at this beach house; I couldn't imagine a better location. Right on the beach, and just a couple of minutes walk to the Siesta Key village. The...
See all reviews
From
$197
Per Night
1 / 22
Payment Protection
Nokomis
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (9) Make Enquiry
4 of 5 stars Reviewed 19 April 2012
If you want to see water from every room,if you want to watch the pelicans nap or if you want to relax next to the water this is the place. This home is situated in a quiet area...
3 of 5 stars Reviewed 6 April 2012
The house was adequate for our needs as we just slept and showered there and went to the nearby public beach every day. We never got in the pool -- it seemed nice enough and...
See all reviews
From
$141
Per Night
1 / 8
Payment Protection
Nokomis
3 Bedrooms, 1 Bathroom, Sleeps 5
Booking
Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 17 August 2014
We stayed here for 3 days on our west coast Florida trip. 3 bedrooms, big yard, Very clean. Very close to several beaches. They even supplied us with beach chairs, umbrella, and...
5 of 5 stars Reviewed 30 December 2013
We stayed here in November over the Thanksgiving holiday into December. The house is very pretty and immaculately clean and in a great spot for everything. The owners were lovely...
See all reviews
From
$147
Per Night
1 / 22
Payment Protection
Venice
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 22 September 2014
My family and I had a wonderful time while at this beautiful, brand new, and completely furnished home. This was our first vacation since our daughter was born, and this place...
5 of 5 stars Reviewed 26 August 2014
We travelled here from the UK with our five year old and one year old sons, his first holiday. This property certainly has the WOW factor, it's spacious, fully equipped with...
See all reviews
From
$745
Per Night
1 / 55
Payment Protection
Venice
6 Bedrooms, 3 Bathrooms, Sleeps 16
Details Reviews (31) Make Enquiry
5 of 5 stars Reviewed 6 March 2013
Very spacious and clean. Close to everything. Plenty of towels, plenty of sheets, plenty of kitchen utensils/pots/pans/dishes. Quick trip to Publix for necessities and we were...
4 of 5 stars Reviewed 8 December 2012
Our family rented this house for Thanksgiving week. All in all, we had a great time - and we found the property manager very responsive to our needs. The house is spacious...
See all reviews
From
$192
Per Night
1 / 16
Payment Protection
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 10 September 2014
Loved it ! Clean, great location and Sandy pleasant to work with , definitely would return ! Walking distance to Village and directly across street to beach.
See all reviews
From
$306
Per Night
1 / 28
Payment Protection
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 25 August 2014
Voltamos depois de 19 anos ao Palm Bay e continua o mesmo porque não pode ser melhor. Nosso apartamento na torre era maravilhoso. Muito bem equipado, não tinha defeito...
See all reviews
From
$1,636
Per Night
1 / 14
Payment Protection
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 18 May 2014
My husband, 2 kids (7&6), and myself have stayed at this condo several times and we highly recommend it to anyone considering a beach vacation in Florida. Bottom line... This...
See all reviews
From
$160
Per Night
1 / 25
Payment Protection
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 6 August 2014
My Husband and I have stayed in this Condo several times. We come back year after year because it is a beautiful condo, clean, comfortable, and the location is perfect. It's...
5 of 5 stars Reviewed 1 August 2014
Working with the owner to arrange our week long stay was very easy! Check in a breeze! The unit was just as pictured and clean! The proximity to the Gulf unsurpassed......steps...
See all reviews
From
$113
Per Night
1 / 22
Payment Protection
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Enquiry
4 of 5 stars Reviewed 23 August 2014
Perfect for getting together with family, walks on the beach and dolphin viewing on the inland waterway. Best of both worlds. The owner was readily available for any problems and...
5 of 5 stars Reviewed 28 May 2014
We had an awesome time at this vacation rental. Elvis, the owner, was very accommodating and catered to our specific needs. The condo was very clean and a nice size, with a...
See all reviews
From
$105
Per Night
1 / 14
Payment Protection
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 5 October 2014
We stayed here for a week (family of 4, kids aged 13 & 11), following on from a fortnight in Orlando. We wanted somewhere to stay where we could walk to a beach. This condo is...
2 of 5 stars Reviewed 1 September 2014
Location, location, location! The condo is a few feet from the busiest road on Siesta Key therefore you hear loud road noise in every room. Hard to believe no one mentioned this...
See all reviews
From
$108
Per Night
1 / 16
Payment Protection
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 18 July 2014
great place, clean and excellent location. dereck was extremely helpful. will stay again. the room is a one bedroom so a little limited in space but i enjoyed it. the outdoor area...
3 of 5 stars Reviewed 13 July 2014
The room was nice, clean, had everything you needed. The beach was farther than 150 yards. Room was quiet until a couple with kids came, you could hear everything. If you don't...
See all reviews
From
$192
Per Night
1 / 17
Payment Protection
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (8) Make Enquiry
3 of 5 stars Reviewed 12 July 2013
place was fair...they charge extra for clean bath towels and charge $75 to clean after you leave!!??
5 of 5 stars Reviewed 13 June 2013
Just returned from a 2 week stay in The Lion suite at The Ringling and it was everything we hoped it would be. Clean, cute and comfortable, well equipped, close to the beach...
See all reviews
From
$245
Per Night
1 / 34
Payment Protection
Venice
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 19 October 2014
Cute, Clean and comfortable with All the conveniences of home. Close to downtown, shopping, and the beach. Would stay again and recommend
See all reviews
From
$518
Per Week
1 / 10
Payment Protection
Venice
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Enquiry
From
$137
Per Night
1 / 22
Payment Protection
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (31) Make Enquiry
5 of 5 stars Reviewed 3 November 2014
Sue was wonderful to us and Ebb Tide is clean, convenient and comfortable. One of our beach chairs was broken and Sue had a new one to us the next morning! The pool is just...
5 of 5 stars Reviewed 26 October 2014
So much more than we expected! Sue thought of everything, from beach bags & towels to kitchen necessities. The back patio is perfect for that morning cup of joe! The pool was...
See all reviews
From
$203
Per Night
1 / 14
Payment Protection
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 15 August 2014
My family and I stayed at Fishermans Cove unit 102 from August 1-13. We found the pictures and description of the condo online to be accurate. The condo included many amenities...
5 of 5 stars Reviewed 24 June 2014
My wife, grown son and I spent a week in this lovely condo directly on the beach on Siesta Key. The condo is a really nice 2 bedroom, 2 bath unit on the first floor so that you...
See all reviews
From
$197
Per Night
1 / 20
Payment Protection
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 1 September 2014
This was my first trip to siesta key and it was the most enjoyable and relaxing vacation I have ever had... My family and I decided to give my brother a going away gift and take...
5 of 5 stars Reviewed 4 August 2014
Great vacation rental. Stayed with my spouse and three kids. Plenty of space and the apartment has everything you will need for a day at the beach (cooler, umbrella, chairs etc...
See all reviews
From
$448
Per Night
1 / 24
Payment Protection
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 12 October 2014
We totally enjoyed every min. It was move in ready all linens washer dryer ect.. Not a problem at all taking the ferry over to beach or short drive to other beaches.
See all reviews
From
$499
Per Night
1 / 34
Payment Protection
Venice
4 Bedrooms, 2 Bathrooms, Sleeps 12
Details Reviews (32) Make Enquiry
4 of 5 stars Reviewed 23 April 2014
Great location, pool was wonderful . House was a little dated but overall clean. We thought they expected a lot of cleaning last day in short time.
1 of 5 stars Reviewed 19 January 2013
This home was not at all what the pictures showed. Everything on the pictures looked new and clean. Of course we could tell it is a older home but it was very upsetting when we...
See all reviews
From
$74
Per Night
1 / 25
Payment Protection
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 18 May 2014
This was a perfect place for my sisters and myself. Total of six women. It was clean and in a quite neighborhood but close to some very good dinning and attractions. Siesta beach...
4 of 5 stars Reviewed 30 June 2013
Comfortable, convenient, affordable. Seems like a great value for the area. Enjoyed my week and would absolutely stay again. Didn’t realize how handy this location would be, it...
See all reviews
From
$137
Per Night
1 / 25
Payment Protection
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (20) Make Enquiry
5 of 5 stars Reviewed 24 June 2014
Ebb tide villa #3 has the feel of home when we come to siesta key Sue is so nice to us when we arrive and when we depart. The place is spotless we have the best time on the...
5 of 5 stars Reviewed 7 October 2012
We just came home from our trip to Siesta Key. What a beautiful place. Ebb Tide was so quiet, relaxing and private. If you are looking to get away from stress then come here and...
See all reviews
From
$853
Per Week
1 / 34
Payment Protection
Venice
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (4) Make Enquiry
From
$147
Per Night
1 / 17
Payment Protection
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (17) Make Enquiry
5 of 5 stars Reviewed 14 April 2014
Perfect condo for a family of five on Seista Key with everything you need already there. Location was peacefully secluded but the bikes provided made the village and beach easily...
5 of 5 stars Reviewed 13 January 2014
My wife and I had a very pleasant stay here. The property is very well maintained and very convenient to everything including the beaches and Siesta Key Village. We especially...
See all reviews
From
$833
Per Week
1 / 28
Payment Protection
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 12
Details Reviews (10) Make Enquiry
From
$589
Per Week
1 / 36
Payment Protection
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Enquiry
From
$834
Per Week
1 / 33
Payment Protection
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (9) Make Enquiry
From
$130
Per Night
1 / 25
Payment Protection
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 31 October 2014
Our family of 4, including an 11 and 7 year old, had a perfectly balanced vacation at this home! We were able to enjoy the gorgeous pool, which kept the kiddos entertained while...
See all reviews
From
$80
Per Night
1 / 10
Payment Protection
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 21 August 2014
If you are looking for somewhere comfortable and clean - this is it! Great view overlooking golf course - swimming pool really close & covered parking space. Everything you need...
See all reviews
From
$130
Per Night
1 / 14
Payment Protection
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 23 August 2014
We enjoyed the cleanliness and excellent location of our cute villa. We were so happy to have everything we would ever need provided to us since we did some cooking there. Had...
5 of 5 stars Reviewed 30 May 2014
Martin & Victoria, My boyfriend and I stayed at your unit for one week after having read about beautiful Siesta Key! Well, Siesta Key was definitely a pleasure, the beach was...
See all reviews
From
$124
Per Night
1 / 16
Payment Protection
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 31 October 2014
This cottage is perfect for a beach vacation...with charming mid century decor, clean, open to breezes, roomy and very efficiently designed. The kitchen supplies and and linens...
4 of 5 stars Reviewed 10 August 2014
The villa totally met our needs: beaches near by (10-minute walk from Crescent Beach and 5-minute drive to Siesta Key Beach), great pool in a relax community, clean house with...
See all reviews
From
$3,497
Per Week
1 / 22
Payment Protection
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 25 March 2014
We had a wonderful relaxing week in this beautifully renovated condo. We loved the panoramic views of the gulf, the proximity to the village and the easy access to the beach...
See all reviews
Go to map view
Book Online(204)
Use filters to find the best results!

Suitability

  • Wheelchair access (74)
  • Elder access (189)
  • Suitable for children (211)
  • Pet friendly (100)
  • Smoking allowed (1)

Amenities

  • Air Conditioning (372)
  • Internet (357)
  • Other outdoor space (308)
  • Parking (285)
  • Washer/Dryer (269)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities