Osprey Rentals

Updating...

age 0-16
647 Results

Relevance

Price: low to high

Price: high to low

Reviews

647 Houses

Dunmore

Osprey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$218

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$161

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

Match: Washing machine

All filters match

Price per night from

$132

Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$161

Great rentals within 20 miles that match your search

Park Model with lanai, large deck, block from pool

Venice house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Washing machine

All filters match

Price per night from

$121

Venice Florida Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$127

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Washing machine

All filters match

Price per night from

$1,000

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$115

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

Match: Washing machine

All filters match

Price per night from

$430

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

Match: Washing machine

All filters match

Price per night from

$155

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Washing machine

All filters match

Price per night from

$230

Tara Golf & Country Club Condo

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

Match: Washing machine

All filters match

Price per night from

$144

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$190

Match: Washing machine

All filters match

Price per night from

$144

Match: Washing machine

All filters match

Price per night from

$285

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$128

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

Match: Washing machine

All filters match

Price per night from

$96

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

Match: Washing machine

All filters match

Price per night from

$163

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Washing machine

All filters match

Price per night from

$161

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

Match: Washing machine

All filters match

Price per night from

$201

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Washing machine

All filters match

Price per night from

$368

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$211

Match: Washing machine

All filters match

Price per night from

$149

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Washing machine

All filters match

Price per night from

$183

Ground Level 2 Bedroom Beach Themed Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$230

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Washing machine

All filters match

Price per night from

$295

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Washing machine

All filters match

Price per night from

$301

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

Match: Washing machine

All filters match

Price per night from

$602

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Washing machine

All filters match

Price per night from

$286

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

Match: Washing machine

All filters match

Price per night from

$195

Luxury Beach Cotttage

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

Match: Washing machine

All filters match

Price per night from

$532

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Washing machine

All filters match

Price per night from

$344

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

Match: Washing machine

All filters match

Price per night from

$453

Luxury Romantic Oceanfront Siesta Beach Condo #304

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!

Match: Washing machine

All filters match

Price per night from

$184

Super clean vacation Villa with Pool

North Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 1 minutes

Match: Washing machine

All filters match

Price per night from

$138

Venice Island Bellagio Home w/ 3BR & 3BA

Venice house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great Vacation” Thanks for allowing us to stay in your beautiful home in Venice Florida. It was very comfortable and had all the convenience of home. Everything we needed was close by (restaurants and grocery store). We really liked the bike trails along the canal since we brought our bikes. We would rent your house again.

Match: Washing machine

All filters match

Price per night from

$104

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

Match: Washing machine

All filters match

Price per night from

$258

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

Match: Washing machine

All filters match

Price per night from

$803

Viewing 38 of 647
rentals in Osprey

×

Also consider