Osprey vacation rentals

4.98 out of 5 average rating, 56 reviews

The outdoor space features a heated pool surrounded by colorful lounge chairs and inflatable pool toys. A shaded seating area is visible, along with a vibrant children's playset in the background. The sky displays a striking sunset, enhancing the relaxing atmosphere.

Home in Bradenton

Sunshine Family Paradise With Heated Pool, Hot Tub

Welcome to your perfect getaway! Located in the heart of the city, our family-friendly retreat offers a perfect blend of comfort and adventure. Dive into a world of nearby activities and attractions, all within easy reach. Enjoy quality time together in our spacious living area or whip up a feast in the fully equipped kitchen. With parks and entertainment just around the corner, every day is an opportunity for fun and laughter. Come and make unforgettable memories in your new home away from home

5 out of 5 average rating, 3 reviews

Apartment in Bradenton

Five Beach Retreat * Best Value @ Shorewalk Resort

Best Value in Shorewalk Resort * Near beaches of Anna Maria Island & IMG Academy Updated. Soothing sandy neutrals and crisp sea blues. Two bedrooms with full baths. Four beds. Two large sofas provide additional sleeping options. Fully stocked with beach gear. Access to the community's resort-style amenities, including 2 relaxing hot tubs, 2 heated pools, lighted tennis and pickleball courts, outdoor BBQ grills, basketball, shuffleboard & bocce ball courts, a billiard room, and a clubhouse.

4.77 out of 5 average rating, 104 reviews

A bright studio apartment features a spacious bed dressed in light grey linens. Two bedside lamps provide soft illumination. A small kitchenette is visible, while a doorway leads to a bathroom with modern fixtures. Natural light enters through a door leading to the private patio.

Apartment in Siesta Key

Gertrude's Siesta | Patio & 1-min to Beach/Village

The Village Studio Top location on island! Apartment with full kitchen, private patio, gated courtyard, in world famous Siesta Village! Leave the car behind and walk to white-sand beaches, 20 bars and restaurants, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Experience a combination of fun ease and relaxation you can't get in other vacations! Book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

4.88 out of 5 average rating, 153 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

4.85 out of 5 average rating, 13 reviews

A spacious living area is illuminated by natural light, featuring a modern layout with an open kitchen and dining space. A large flat-screen TV is mounted on the wall, while seating positions at the island create an inviting atmosphere. Decorative plants add a touch of greenery.

Home in Venice

Sunset Breeze Retreat

Welcome to your serene getaway in South Venice, FL! This cozy and spacious home is your perfect retreat, just minutes from breathtaking beaches and charming local shops and restaurants. Inside, unwind in comfort and style, with plenty of room to relax and enjoy quality time with loved ones. Embrace fun-filled evenings with a foosball table or savor the outdoors with a grill and beach supplies at your fingertips. Your dream vacation awaits in this inviting haven of relaxation and adventure.

4.97 out of 5 average rating, 37 reviews

Condo in Sarasota

Siesta Key Village & Beach w pool & pet friendly

Location and value. No fighting traffic for hours to get to Siesta Key. Park the car and relax. The heart of Siesta Key village waits just outside the back door, and everything is within walking distance at this centrally located condo with a heated pool. The #1 voted beach in the USA and its powder soft sugar sand is an 7-minute walk. Paradise and serenity have been found. One of the few places that will allow your small dog to stay. Also one of the few you can rent for less than a week.

4.91 out of 5 average rating, 23 reviews

Home in North Fort Myers

Paradise Found

PARADISE FOUND, you can vacation right here at your own LAKE SIDE PARK! Stunning, peaceful & beautiful waterfront property with your own little island. Fish, bird watch or feed the turtles from your private dock or double arched bridge. Huge back yard for enjoyment & safety of children & pets. Your vacation home has a sunny disposition & soaring ceilings. First floor master suite with sliders to pool/lanai. Two story ceilings in livingroom & gorgeous staircase to guest suites.

4.91 out of 5 average rating, 11 reviews

Slowtide Cottage on Siesta Key

A high-end luxury cottage retreat on Siesta Key. No parties here -- the space was designed and outfitted for those who want a quiet place to relax. 2 bed 2 bath Cottage situated on the Intracoastal water of Siesta Key adjacent to the community pool, tiki bar, fishing dock, fishing pier and deeded private beach access. Meticulously remodeled former ww2 USAAF Barracks from the old SRQ Air Force Base. All new electrical, plumbing, lighting (Buster & Punch), Arhaus furniture.

An outdoor space features a modern tabletop air hockey game and a classic skee-ball machine, inviting friendly competition. The area is surrounded by a lush green garden, with wooden fencing providing privacy, while natural light streams in through screened windows.

4.95 out of 5 average rating, 19 reviews

Warm, Luxury Oasis in Central Sarasota

Choose to stay at a home which has it all. Professionally designed and hosted by a 10-year SuperHost, this property offers incredible value. Superbly comfortable beds and linens, SUPER FAST internet, thoughtful furnishings, tons of activities & games, fully equipped for babies and toddler needs, extremely central location, large, high-end TVs, a jacuzzi, 2-person hammock, in-ground fire pit…. And fur babies welcome… you name it, this home has it. Welcome to Sarasota Paradise.

A spacious living area features a light gray sofa arranged around a dark coffee table, with a neutral area rug underneath. A flat-screen television is mounted on the wall, and large windows allow natural light to illuminate the space, creating a welcoming environment.

4.98 out of 5 average rating, 390 reviews

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

5 out of 5 average rating, 11 reviews

An outdoor dock area features several wooden Adirondack chairs in a warm orange hue, positioned by calm water. Sturdy posts with lantern tops line the dock, surrounded by lush greenery and palm trees. A clear sky and distant homes create a serene waterfront setting.

Home in Punta Gorda

Stunning! Luxury waterfront home

STUNNING!! LUXURY WATERFRONT HOME - HEATED POOL- Close to Harbor/Fish Village -PREMIER HOST reviews averaging 5.0 since 2018 on other site. -Modern, newly updated home with open layout allowing for enjoyment of the cool waterfront breezes. -Boat dock with very close Harbor access within 10 minutes. -Southern exposure, full sun, heated pool, and waterfront. Oversized pool extends along large portion of rear of home.

5 out of 5 average rating, 12 reviews

An inviting outdoor space features a heated pool surrounded by a tropical landscape. A staircase leads to the upper level, while lounge seating is arranged nearby. Sunlight reflects off the water, creating a serene atmosphere for relaxation.

Condo in Sarasota

100' from the beach, Spacious 2BR Beachside Oasis

Discover the allure of Siesta Key from the comfort of this 1200 sqft vacation rental, perched on the 2nd floor of the Point of Rocks Trip-Plex the peaceful Point of Rocks neighborhood. This two-bedroom, two-bath unit is an ideal retreat for families or groups seeking a blend of luxury, comfort, and accessibility to the beach.

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Popular amenities for Osprey vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Osprey's top sights

Historic Spanish Point73 locals recommend

Casey Key Fish House66 locals recommend

Ophelia's on the Bay64 locals recommend

Stoneybrook Golf & Country Club8 locals recommend

Turtles Restaurant23 locals recommend

Turtle Beach Grill Restaurant18 locals recommend

Other great vacation rentals in Osprey

5 out of 5 average rating, 8 reviews

A wooden dock extends over calm waters, with boats moored alongside. Lush greenery borders the scene, and distant homes can be seen on the horizon. The sky is clear, contributing to the serene atmosphere of the waterfront setting.

Home in Placida

Bay view and possible two family rental!

4.93 out of 5 average rating, 27 reviews

A tranquil beach scene features clear turquoise waters with gentle waves lapping the shore. Several individuals are seen swimming and enjoying the water, while the sandy beach stretches under a blue sky dotted with soft clouds. Sparse greenery lines the beach in the background.

Home in Nokomis

Last minute May ,house 2 Mil beach .Pets welcome

4.89 out of 5 average rating, 27 reviews

A cozy bedroom is presented, featuring a spacious bed with a wooden frame. Two bedside tables with matching lamps provide soft lighting. Dark curtains frame the windows, and the wooden flooring adds warmth to the room's neutral tones.

Home in Venice

Second home vacation rental

5 out of 5 average rating, 4 reviews

A single-story house is framed by lush greenery and plants, with a well-kept lawn in the foreground. A driveway leads to a garage door, while a covered porch is visible with outdoor seating for relaxation.

Home in Bradenton

Cottage by the Sea

4.99 out of 5 average rating, 83 reviews

A canopy of sprawling oak trees extends over a paved road, creating a natural tunnel. The tree branches are adorned with Spanish moss, and a white fence lines the pathway, enhancing the serene outdoor setting.

Camper/RV in Sarasota

HOME HOME ON THE RANCH. SARASOTA FL.

5 out of 5 average rating, 6 reviews

Home in Bradenton

Luxury ~ Heated Pool ~ Games ~ near AMI, IMG, SRQ

4.76 out of 5 average rating, 135 reviews

A spacious green lawn extends towards a peaceful lake, surrounded by lush trees and plants. The calm water reflects the serene natural setting, and a wooden platform is positioned at the water's edge, adding a place for enjoyment and relaxation.

Home in Venice

Vacation home by Shasta Rd