Fitness-friendly holiday rentals in Osprey

A heated pool is surrounded by a tiled deck, with lounge chairs available for guests. Palm trees and blue umbrellas create a tropical atmosphere, while the beach and ocean are visible beyond the pool area under a clear blue sky.

4.94 out of 5 average rating, 146 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

4.89 out of 5 average rating, 175 reviews

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

Home in Sarasota

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

Guest suite in Port Charlotte

4.96 out of 5 average rating, 160 reviews

Garage to a Tiny House Studio Near Shopping Center

Experience comfort and style in this charming, pet-friendly space, perfect for short getaways. Enjoy the privacy of your own entrance, along with a full shower, cozy living room, dining area, and bedroom, all within one convenient layout. The fully fenced backyard, shared with other tenants, features a grill and fire pit—ideal for relaxing evenings outdoors. While the space includes a kitchenette, access to the main shared house may be available if you need a full kitchen or laundry facilities.

4.92 out of 5 average rating, 108 reviews

Home in North Port

Private Heated Pool/Spa, 4bed/2bath, Fenced Yard

Welcome to Paradise! This 4 bed/ 2 bath dog friendly, heated pool & spa home features a large fenced in yard and oversized lanai area. It sleeps up to 6 guests & offers plenty of gathering space. Located within 15 minutes to Warm Mineral Springs, Atlanta Braves Spring Training and 30 minutes to Englewood/ Venice beaches. Located 5 miles off I75 & close to all the attractions of beautiful southwest FL. This home provides the perfect combination of a country home while being close to everything.

4.96 out of 5 average rating, 110 reviews

The spacious living room features a light blue color palette while natural light enters through the windows. A large flat-screen TV is mounted on the wall above a sleek black entertainment unit. Cozy seating arrangements, including a sectional sofa and a coffee table, create an inviting area.

Condo in Venice

Spacious Downtown Venice Island Condo Near Beach

Large, quaint, quiet condo in the heart of downtown Venice Island. Short walking distance to all the idyllic downtown shops, restaurants, entertainment, bars, arts & a quick bike ride to an amazing beach. Bikes included. Very spacious & well equipped rental suitable for short or long-term visits. Large fully equipped kitchen. Lots of amenities & beach gear! Comfy king bed. Free parking. Venice Beach 1.1 miles / Sharkey's Restaurant & Pier 1.7 miles / Coffee shop & downtown just 3 blocks away.

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.86 out of 5 average rating, 105 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

A light-filled living area features a comfortable white sectional sofa with decorative pillows, complemented by a wooden coffee table. Large glass doors lead to an outdoor space, while a television and two lamps enhance the room's functionality and warmth.

4.84 out of 5 average rating, 121 reviews

The Palm Bay Club on Siesta key Beach

Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

A circular heated pool is framed by palm trees and lounge chairs. The clear blue water reflects the sky, while blue umbrellas provide shade in the background. A pathway leads to the beach, enhancing the view of the ocean beyond the pool area.

4.82 out of 5 average rating, 143 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Our newly renovated condo is located on Siesta Key's award winning Crescent Beach. Our unit is has all of the amenities of home for your convenience. The primary bedroom has a king sized bed and its own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 377 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. If we are booked check out our additional units under our profile.

4.89 out of 5 average rating, 219 reviews

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

A tranquil pool area is surrounded by palm trees, reflecting the clear blue sky. Lounge chairs are positioned around the pool's edge, inviting relaxation. The sun casts a warm glow over the scene, enhancing the peaceful ambiance of the resort.

4.98 out of 5 average rating, 130 reviews

Siesta Key For Me @ The Palm Bay Club

🏖️ Newly Renovated Siesta Key Condo | Ocean + Bay Views | Sleeps 6 📍 Bayside Suite at The Palm Bay Club | Walk to Beach ✨ ALL-NEW RENOVATIONS MAY 2025! Brand new bathrooms, flooring, doors, trim, granite countertops & more—be among the first to enjoy our stylish upgrade! Welcome to Condo #310 at The Palm Bay Club—a 2BR/2BA bright and breezy bayside condo with water views, modern upgrades, and private beach access just a short walk away. Sleeps up to 6 guests comfortably.

A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.

4.97 out of 5 average rating, 120 reviews

Palm Bay Club! Resort Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Popular amenities for Osprey fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-Friendly apartment accommodation

Apartment in Downtown Sarasota

5 out of 5 average rating, 6 reviews

Pickleball, Kayak, LegacyTrail, Beaches, Downtown

Superhost

Apartment in Sarasota

4.61 out of 5 average rating, 36 reviews

[S] 2/2bedr&bath condo, pool,close to Siesta Beach

Apartment in Downtown Sarasota

A cozy bedroom features a queen-sized bed with white linens and a decorative pillow. Soft light from two bedside lamps enhances the warm wooden accents. The room includes two windows with wooden blinds, allowing for natural light, and a piece of artwork is prominently displayed on the wall.

4.9 out of 5 average rating, 167 reviews

Adorable Historic & Charming Walkable Safe Area

Apartment in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 166 reviews

Free Prkn, Early Chkin, Elevator-4th fl airport/DT

Superhost

Apartment in Longboat Key

4.77 out of 5 average rating, 26 reviews

Private Beach, Outside Patio with Full Gulf View

Apartment in Port Charlotte

An aerial view captures a waterfront community along the Myakka River. The image highlights the blue rooftop condos nestled among lush greenery, with a serene water expanse stretching into the horizon. The area is marked by a wooden pier extending into the river.

4.89 out of 5 average rating, 19 reviews

Waterfront Condo w Scenic Views-Heated Pool

5 out of 5 average rating, 27 reviews

A spacious living area features large windows that offer views of the outside greenery. Comfortable seating includes a sofa and two chairs, complemented by a dark wood coffee table. A dining area is visible with a round table and four chairs, and a mirror reflects natural light.

Apartment in Sarasota

Beautiful Top Floor Serenata 2Bd/2Ba Apartment

4.92 out of 5 average rating, 12 reviews

Apartment in Siesta Key

Gertrude's Siesta | Palm-view Pools Private-Beach!

Fitness-friendly condo rentals

The living area features two brown leather sofas flanking a wooden coffee table, with a decorative plant beside an illuminated lamp. Natural light enters through a large window, while a light blue wall and patterned rug enhance the comfortable surroundings.

4.95 out of 5 average rating, 55 reviews

Spectacular Siesta Key Beachfront Condo

Condo in Indian Beach-Sapphire Shores

5 out of 5 average rating, 14 reviews

Modern 1/1.5 Waterfront at The Strand

A clear view of the ocean is presented, complemented by lush greenery in the foreground. Buildings line the coastline, and a blue sky with light clouds enhances the scene, creating an atmosphere of tranquility and connection to nature.

4.97 out of 5 average rating, 31 reviews

Penthouse Expansive Ocean Views

A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.

4.91 out of 5 average rating, 120 reviews

The Honeymoon Suite on Siesta Key Beach

Superhost

A private beachfront terrace offers sweeping views of the Gulf, where soft sand and palm trees are visible. Comfortable seating is arranged on the patio, complemented by a coffee table and a round dining table, all under a ceiling fan and wooden overhang.

5 out of 5 average rating, 4 reviews

Direct Gulf View - Residence 307

4.89 out of 5 average rating, 19 reviews

Beautifully Remodeled Stylish Condo in Sarasota

Condo in Indian Beach-Sapphire Shores

A circular pool is surrounded by modern white buildings, with palm trees dotting the perimeter. The clear blue water reflects the sky, and a poolside lounge chair is positioned near the edge. Paved stones create a pathway around the pool area.

5 out of 5 average rating, 43 reviews

Chill Sarasota Hideaway

5 out of 5 average rating, 9 reviews

Johnnys Island Palm | Walk to Beach & Dining

Fitness-Friendly Holiday House

A modern bedroom features a four-poster bed dressed in neutral linens, complemented by wall-mounted lamps. A decorative bench is placed at the foot of the bed. Natural light fills the room through large sliding glass doors that open to a private balcony.

4.91 out of 5 average rating, 148 reviews

4BR Golf View-Heated Pool/IMG Academy/Near Beaches

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 114 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

4.9 out of 5 average rating, 10 reviews

Home in Rotonda West

Luxury House Florida, Golf View, Privacy Pool.

4.98 out of 5 average rating, 173 reviews

Home in Bellevue Terrace

LUXE home 6mi to Siesta w/ incredible pool area!

4.92 out of 5 average rating, 60 reviews

A swim spa is illuminated by soft, colorful lighting, offering a tranquil setting for relaxation. Surrounding the spa, a landscaped area features stepping stones and decorative pebbles, with tropical plants and trees creating a serene atmosphere. Ambient lighting along the path enhances the outdoor space.

Home in Sarasota

SARASOTA PLACE NEAR SIESTA BEACH

4.92 out of 5 average rating, 133 reviews

A quaint beach house is surrounded by lush greenery and palm trees, featuring a sandy front yard. A wooden deck with two blue chairs offers an inviting spot for relaxation. The house showcases a cheerful yellow exterior, complemented by vibrant landscaping.

Home in Longboat Key

Longboat Key Beach House

A screened-in private pool area is visible, featuring clear water that reflects sunlight. The surrounding yard is spacious and fenced, providing a serene environment for relaxation.

4.96 out of 5 average rating, 25 reviews

Coastal Manor | Heated Pool · Dogs Welcome · LWR

A serene outdoor space showcases a sparkling pool framed by lush tropical landscaping. Palms and vibrant plants surround the area, with a flamingo statue in the foreground. Soft lighting from string lights enhances the tranquil atmosphere as the sky transitions to dusk.