Last‑Minute Sarasota Vacation Rentals, Beach Homes & Condos Still Available

Vacation Rental in Sarasota 5.0 Star Review

Come and enjoy a stress free vacation at this island paradise three bedroom two bath private home with heated pool. The property has recently been renovated and finished with all new furniture throughout. Pulling up to this private home via the circular drive you will be greeted by its Key West style exterior surrounded by lush tropical landscaping. Enter the home through french doors and notice the volume ceilings and open spaces. To the right you enter the spacious family room furnished with a large comfortable sofa and 55" flatscreen smart TV. This great room is also furnished with a queen-.......

3 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Come enjoy the relaxed vibe of Siesta Key! The beautiful white sand beaches that make Siesta Key the #1 beach in the US are not even a five-minute stroll away. Siesta Key Village and the famous 3 miles of the softest 99.. This two story, 4 bedroom 3 1/2 bathroom home features a huge heated pool with spa and an incredible outdoor living space for relaxing to the soothing sounds of the pools water features or livening things up and entertaining your family and guests. The property is private and secluded from neighbors and surroundings by a wall. As you enter through the front door on the main l.......

4 Bedrooms - 3 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.8 Star Review

Villa Youppie *This home has a minimum of 90 days You will love our beautifully maintained and clean Villa Youppie in Sarasota. It is located at the corner of a lake which provides lots of privacy and thanks to a southern exposure you have sun in the pool and on the patio all day long. New travertine tiles on the patio, granite counter tops in the kitchen, nice wood floor and wood ceiling in the dining room. Access to pool from Master Bedroom. The entire house is equipped with wireless high-speed internet, there are 3 flat screen TVs a DVD player, a stereo system and much more. The kitchen and.......

4 Bedrooms - 3 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 3.0 Star Review

Your Ultimate Beach Escape on Lido Key, Florida — Steps from the Sand & St. Armands Circle NEWLY RENOVATED!!! Ready for the ultimate Lido Beach getaway? This charming unit offers the perfect launchpad for your Florida adventures, delivering incredible access to all the Lido Key magic! Step inside to a comfortable haven designed for relaxed beach living. You'll find a king-size bed in the primary bedroom for peaceful nights, and a queen-size bed in the second bedroom, providing ample space for your group. The living room features a smart TV and a cozy seating area with a sleeper sofa, while t.......

2 Bedrooms - 1 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Let's be ’s better at the beach! Come play in the sand with a drink in your hand on Lido Key Beach, FL! NEWLY RENOVATED!!! Ready to swap your shoes for flip-flops? Discover Mermaid For A Day, a vibrant studio unit on Lido Key, offering the ultimate beachside escape! This is where comfort meets unparalleled convenience, putting you right in the heart of Lido's magic. Inside, you'll find everything you need for a carefree vacation: a cozy king-size bed for restful nights, a refreshing walk-in shower, and a full kitchen ready for your beach-day snacks or morning coffee. The living area is desig.......

Studio 1 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Downtown Sarasota Private Vacation Home - Minutes to Lido Key Beach, St. Armands Circle, and all that Downtown Sarasota, FL has to offer! Our 3-bedroom, 3 Bathroom private vacation home offers a fantastic property perfect for your relaxing South Florida Gulf Coast Vacation. - 3 Bedrooms / 3 Bathrooms - 5 miles to popular Gulf Coast Beaches - Fully Equipped Kitchen - Dining for 4 at the dining table - Spacious Patio and Backyard with outdoor seating area - Parking for three cars in the driveway - Beach Equipment for guest use (Beach Towels, 4 Chairs, and a Cooler) - Baby and Child Items Availab.......

3 Bedrooms - 3 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.8 Star Review

Welcome to paradise! - Beautifully updated 2-bedroom, 2-bath condo - Remodeled bathrooms and new wood laminate floors - Hurricane windows for safety and ocean views - Heated pool and grilling area for outdoor enjoyment - Freshly painted interior with modern fixtures - Indulge in the epitome of coastal living with this impeccably updated 2-bedroom, 2-bathroom condo nestled alongside the stunning shores of Crescent Beach. Here are the important policies and guidelines to note for your stay: Check-in: You can check in anytime after 4:00 PM. The property will be prepared and ready for your arrival.......

2 Bedrooms - 2 Baths - Sleeps 5
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.8 Star Review

Welcome to your exclusive coastal retreat! - 2-bedroom, 2-bathroom condo steps from Crescent Beach - Freshly painted interiors with chic fixtures - Heated pool and grilling area for year-round relaxation - Panoramic ocean views through hurricane windows - Perfect blend of privacy and convenience Your exclusive slice of paradise! Here are the important policies and guidelines to note for your stay: Check-in: We facilitate self-check-in, and guests are welcome to check in any time after 4 pm Check-out: We kindly ask that you check out on or before 10:00 AM on your departure date. This allows us .......

2 Bedrooms - 2 Baths - Sleeps 5
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Welcome to your Siesta Key retreat! - Beautiful 2-bedroom, 2-bath condo for 6 guests - Renovated in May 2022 with modern decor - Spacious living area with smart TV and enclosed lanai - Fully equipped kitchen with granite countertops - Shared pool and hot tub for relaxation - Beach essentials provided, including towels and snorkeling gear - Quiet neighborhood with cafes and nightlife - Once you parked you don't need to drive again. Here are the important policies and guidelines to note for your stay: Check-in: You can check in anytime after 4:00 PM. The property will be prepared and ready for y.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Experience the ultimate Siesta Key lifestyle in this luxurious 6BR retreat. - Private pool and spa - Gourmet kitchen with granite countertops - Smart home features with intercom and alarm system - Spacious game room and movie theater - Lush tropical landscaping - Deeded beach access - 800 feet from Bayfront Marina Exceptional Siesta Key Oasis with 6 Bedrooms, Deeded Beach Access, and Luxury Amenities! Here are the important policies and guidelines to note for your stay: Check-in: We facilitate self-check-in, and guests are welcome to check in any time after 4 pm Check-out: We kindly ask that y.......

6 Bedrooms - 4 Baths - Sleeps 14
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Presents: Bahama Breeze! This beautiful coastal home is nestled in the heart of Sarasota, just 15 minutes away from both Lido Key Beach and Siesta Key Beach! With a backyard oasis, this cozy home is a haven to return to after a day at the #1 beach in the US, Siesta Key Beach! - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Outdoor TV - Located Next to the Gorgeous Legacy Trail! - Grill - Adult Bikes - Outdoor Dining + Sitting Area - Private Backyard - Beach Supplies Wake up with your morning cup of coffee enjoyed from the beautiful screened-in porch overlooking the ba.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Hyde Park Villa! This charming and stylish 3-bedroom home is nestled in the heart of beautiful Sarasota, just 15 minutes away from BOTH Lido Key and Siesta Key Beach! This villa has every amenity and luxury that you need for your next dream vacation, including: • Private Heated Saltwater Pool • Indoor Fireplace • Stylish Design • Outdoor Oasis w/ Beautiful Fenced-In Backyard • Master Bath w/ Soaker Tub • Outdoor Dining Area + Propane Grill Welcome to our luxurious oasis with soaring high ceilings and exquisite stylish design! This stunning home is the epitome of elegance,.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Honey Glow Bungalow! This beautiful home in the heart of Sarasota is the ultimate destination for embracing the radiant Florida sun and nearby beaches with your loved ones! This beautifully designed home, located just 20 minutes away from both Siesta Key and Lido Beach, includes: - Backyard Guest House - 55" Smart TV - Patio w/ Fire Pit - Screened-In Porch - Board + Card Games - Highchair + Pack N Play - Private Backyard w/ BBQ Grill - Spike-Ball, Corn Hole + Kan Jam - High-Speed Wi-Fi (Perfect for Remote Work!) Step inside this charming retreat and embrace its inviting interior. A f.......

3 Bedrooms - 3 Baths - Sleeps 7
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Coastal Cottage! Vacation in a slice of paradise, just minutes away from the delightful Amish community of Pinecraft in picturesque Sarasota, Florida. This peaceful neighborhood invites you to savor leisurely strolls along its serene streets and days in the sun at nearby Siesta Key Beach (just 20 minutes away!). This incredible home includes: - Backyard Oasis w/ Fire Pit + Magical String Lights ​​​​​​​- Covered Back Porch w/ Egg Chairs! - Private Backyard - Outdoor Seating + Dining - Beautifully Designed Interior w/ High Vaulted Ceilings - Spacious Fully-Equipped Kitche.......

3 Bedrooms - 3 Baths - Sleeps 9
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Presents: Paradise Palms! Pristine home in the heart of a quiet neighborhood in Sarasota minutes from Downtown! Located just 18 minutes away from both 5 star beaches Siesta Key and Lido Beach, this incredible home includes: - Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st ​​​​​​​- Hot Tub - Cold Plunge - Lounge Chairs + Egg Chairs! - Phillips Espresso Machine + Syrups - YoutubeTV included - Foosball Table - Pet Friendly home ​​​​​​​- Spacious Fully-Equipped Kitchen - Private fenced in Backyard w/ Lawn Games + Grill When you first step into P.......

3 Bedrooms - 2 Baths - Sleeps 7
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Waldemere House Located in a beautiful neighborhood just steps away from Arlington Park, and just 15 minutes away from Siesta Key and Lido Beach, this gorgeous and spacious Sarasota home is your DREAM vacation destination! This home has something for everyone in your group, including: - Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Large Pool Deck fully fenced in - 2 Electric Bikes - Close access to tennis courts, an aquatic center, gym, playground, and more - Beach Supplies, Toys, and Towels Provided - Screened-In Porch - Yard Games: Corn Hole + Kan Jam -.......

3 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from BOTH Lido Key and Siesta Key Beach, this incredible stay includes: - Backyard Putt-Putt Course - Private Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Expansive Covered Lanai featuring 12' High Ceilings, Magical String Lights, Cooling Fans, Plush Swivel Glider Recliners & Deep Seating Sofa - Jura Espresso Machine: we have .......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Costa Del Ray! Nestled in the radiant heart of Sarasota, just 15 minutes away from both Lido Key Beach and Siesta Key Beach, we invite you to immerse yourself in the epitome of coastal luxury and rejuvenation. This dream destination includes : - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Patio - Workout Room - Work Space w/ Lightning Fast Wi-Fi - Beach Supplies + Towels Provided - Stylish Design Indulge in this gorgeous beach oasis, with all of its luxurious amenities! Enjoy your morning cup of coffee from the comfort of the covered patio, then spend the .......

4 Bedrooms - 2 Baths - Sleeps 10
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.8 Star Review

Presents: The Airy Bungalow! Experience our newly-enhanced retreat, located in the heart of Sarasota, just 15 minutes away from the beach! This gem boasts a brand-new pool and a fabulous outdoor kitchen that's bound to elevate your stay! This incredible home includes: - Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st - Built in Hot Tub - Outdoor Kitchen ​​​​​​​- Outdoor Dining Set- Seats 8 - Ping Pong Table - Kids Toys - Grill As you step into the bungalow, you are greeted with a chic boho design and plenty of windows that flood the space with the natural .......

4 Bedrooms - 2 Baths - Sleeps 9
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Moroccan Bungalow! Step into the enchanting world of the Moroccan Bungalow. This spacious coastal stay promises to leave you spellbound. Located just 15 minutes away from BOTH Siesta Key and Lido Beach, this incredible stay includes: • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • Screened-In Porch • Museum-Like Moroccan Themed Home • South Facing Pool (More SUN!) • Fully-Equipped Kitchen • Lightning Fast Wi-Fi for Remote Working Moroccan Bungalow is a breathtaking 3-bedroom, 2-bath haven that welcomes you to a realm of luxury and cultural allu.......

3 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Sandy Feet Retreat! Experience this entertaining and inviting home in the heart of Sarasota, Florida! Just 10 minutes away from the beaches and downtown, this home has something for everyone, including: • Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st • Putting Green • Ping Pong! • Beautifully Decorated Interior • INCREDIBLE Backyard w/ Nest Chairs, Grill, Outdoor Seating + Lounge Chairs! • Fully-Equipped Kitchen + More! Get ready to sip your morning cup of coffee from the incredible backyard oasis, or from the beautiful living room. This home has.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Presents: Sea Esta! Experience this stunning, newly-renovated home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis with a heated saltwater pool and putting green, this home has everything that you and your loved ones need for your next dream vacation, including: • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • Turf in the Back Yard w/ a Putting Green • Sun Deck in Pool w/ Lounge Chairs • Pool + Beach Supplies • Resort-Like Back Yard w/ a Pergola • Fun Outdoor Swingin.......

3 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Sapphire Shores! Welcome to this breathtaking 3-story sanctuary, nestled in the heart of Sarasota, Florida! Just 15 minutes away from the beaches and downtown, this luxurious property offers a true haven of opulence and relaxation! This destination has an extensive amenity list, including: - Private 40' Lap Pool w/ Sun Decks - Ocean Views From The Home - Fireplace - A Game Room - 2 Bars - Kayaks + Bikes - Jura x8 Espresso Machine - Private Balconies off of Each Room w/ French Doors! Experience this incredible home, where the attention to detail can be felt throughout the entire home!.......

5 Bedrooms - 5 Baths - Sleeps 10
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Sea Pointe! Step into your newly furnished coastal haven in beautiful Sarasota, Florida. Nestled in the heart of a tropical paradise, just 15 minutes away from the beach, this exquisite property promises an enchanting getaway for those in search of ultimate relaxation and rejuvenation. Your extensive amenity list includes: - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Indoor Hanging Swing - 55" Outdoor TV - Outdoor Lounge Furniture - Pet Friendly!!! - Patio + Grill Experience the Sunshine State from the comforts of this beautiful coastal home! When you fir.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Presents: Sunshine Haven! This spacious property is ideal for your next family or friend's getaway to Sarasota, FL. Dive into the above-ground pool secured by a locked gate, relax under the pergola, and enjoy outdoor grilling and games. Your perfect blend of comfort and recreation awaits! • Above Ground Heated Pool - heated at NO extra cost from Nov 21 - April 1st • Shuffleboard Court! • Pergola • Fire Pit • Basketball Court • Grill • Putting Green • And so much more! Experience the ultimate getaway at our charming short-term rental property in Sarasota, FL. This spacious haven.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Bay Bliss Bungalow! When renovating this home, we crafted every detail to blow our guests away! Step into your dream getaway in paradise. Located just 20 minutes away from Siesta Key Beach, this home has everything that you and your loved ones need for the vacation of your dreams, including: - Covered Porch w/ String Lights - 2 Electric Bikes - Cozy Outdoor Furniture Set - Spacious Living Room - 65" + 55" Smart TVs! - Fully-Equipped Kitchen + Laundry Room When you first enter the home, you are greeted with a beautiful open-floor plan, high vaulted ceilings and gorgeous decor! Our new.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

Presents: Royal Palms Oasis! This incredible pet-friendly stay in Sunny Sarasota is your dream vacation in paradise! Located in the heart of Pinecraft, just 15 minutes away from Siesta Key Beach. The home is fully loaded with family friendly amenities: - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Pickleball Court (not regulation size) - Putt Putt Course - Shuffleboard Court - Basketball Court - 2 Living Rooms! - Pet-Friendly w/ Private Backyard ​​​​​​​- Pool + Beach Supplies When you first enter the home, you are greeted with not one, but TWO living r.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Presents: The Palmy Pickle Newly renovated space in Sarasota, FL with private pickleball court, fire pit, lanai, and more! Located in the heart of Pinecraft, just 15 minutes away from Siesta Key Beach, This dream stay has something for everyone including: - Pickle Ball Court (regulation size) - Fire Pit - Lanai ​​​​​​​- Infinity Game Table - Beach Supplies Experience the ultimate Florida escape at our delightful 3-bedroom, 2-bath rental! Challenge friends on the private, colorful pickleball court, relax around the cozy fire pit, or kick back on bean bags in the lanai. Inside, enj.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Steps to everything pet-friendly downtown Sarasota has to offer! Walk or bike to restaurants, shops, marina, Bayfront, Whole Foods, Coffee Shops, Opera or Symphony 7 minutes to Lido Key Beach and St. Armands Circle 6 minutes to Ed Smith Stadium Oriole's Baseball, Ringling College, Opera, Symphony 5 minutes to the 54 acre Bay Park & Marina Jacks 2 minutes to Main Street Restaurants, Shops, Spirits and Live Music 2 minutes to Starbucks and Coffee Houses 2 minutes to Publix and Whole Foods 15 minutes to Siesta Key Step across the street to the 10 acre Park with 2 Dog Parks, Playground, Tennis, Pi.......

3 Bedrooms - 3 Baths - Sleeps 10
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Key Differentiators & Amenities ∆ Central downtown Sarasota—walk to shops, restaurants, arts venues, and marina ∆ 1 spacious bedroom, 1 updated bathroom (perfect for couples, solo travelers, or business guests) ∆ Pet-friendly: beds, bowls, blankets, waste bags, and secure fenced dog run provided ∆ Free reserved on-site parking—rare downtown convenience ∆ High-Speed WiFI throughout unit ∆ WorkSpace Desk for Remote Work to be accomplished ∆ 2 Smart TVs with streaming services ∆ Fully equipped kitchen with modern appliances and generous storage ∆ Comfortable Living Area ∆ .......

1 Bedrooms - 1 Baths - Sleeps 3
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Key Differentiators & Amenities ∆ Central downtown Sarasota—walk to shops, restaurants, arts venues, and marina ∆ 1 spacious bedroom, 1 updated bathroom (perfect for couples, solo travelers, or business guests) ∆ Pet-friendly: beds, bowls, blankets, waste bags, and secure fenced dog run provided ∆ Free reserved on-site parking—rare downtown convenience ∆ High-Speed WiFI throughout unit ∆ WorkSpace Desk for Remote Work to be accomplished ∆ 2 Smart TVs with streaming services ∆ Fully equipped kitchen with modern appliances and generous storage ∆ Comfortable Living Area ∆ .......

1 Bedrooms - 1 Baths - Sleeps 2
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Steps to everything pet-friendly downtown Sarasota has to offer! Walk or bike to restaurants, shops, marina, Bayfront, Whole Foods, Coffee Shops, Opera or Symphony 7 minutes to Lido Key Beach and St. Armands Circle 6 minutes to Ed Smith Stadium Oriole's Baseball, Ringling College, Opera, Symphony 5 minutes to the 54 acre Bay Park & Marina Jacks 2 minutes to Main Street Restaurants, Shops, Spirits and Live Music 2 minutes to Starbucks and Coffee Houses 2 minutes to Publix and Whole Foods 15 minutes to Siesta Key Step across the street to the 10 acre Park with 2 Dog Parks, Playground, Tennis, Pi.......

3 Bedrooms - 3 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

Indulge in resort-style living near Siesta Key in Sarasota! - Luxurious 4-bedroom retreat for up to 10 guests - Elegant interiors with a gourmet kitchen - Spacious patio and refreshing pool - Minutes from Siesta Key's beaches, dining, and attractions - Perfect blend of relaxation and convenience Step into your own private oasis near Siesta Key in Sarasota! Here are the important policies and guidelines to note for your stay: Check-in: You can check in anytime after 4:00 PM. The property will be prepared and ready for your arrival. Check-out: We kindly ask that you check out on or before 10:00 .......

4 Bedrooms - 2 Baths - Sleeps 10
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Casa Tranquilo! Book this beautifully renovated 3-bedroom, 2-bath modern home in an upscale Sarasota neighborhood, just 11 minutes from Siesta Key Beach. Ideally located near Siesta Key Village, Trader Joe’s, bike rentals, and local favorites like Rico’s Pizza & Pasta, it’s the perfect spot for both relaxation and convenience. LOCATION HIGHLIGHTS: - Upscale Sarasota neighborhood - Just 11 minutes to Siesta Key Beach - 3.5 miles to Siesta Key Village for dining, shopping & nightlife - Close to Trader Joe’s, bike rentals, and casual dining like Rico’s Pizza & Pasta PROPERT.......

3 Bedrooms - 2 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Welcome to Siesta Sands Beach Resort 4th Floor with Elevator! This gorgeous south-end Siesta Key condo sits on the Gulf of Mexico in a gated complex with private beach access and two heated pools. Enjoy endless beach activities—swim, build sandcastles, rent jet skis, or relax under an umbrella with a good book. Take in stunning sunsets, collect seashells, or simply lounge poolside for the ultimate coastal getaway. LOCATION HIGHLIGHTS: - South end of Siesta Key, on the Gulf of Mexico - Gated beachfront complex with private beach access & shower - Easy access via South Siesta Key Bridge - Fr.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Welcome to your Lido Key Coastal Retreat! Discover the perfect blend of relaxation and convenience in the heart of Lido Key. This bright, elevated 2-bedroom duplex offers the ultimate Florida location: just a 6-minute stroll (0.3 mi) to the sand and sunsets of Lido Beach and a 7-minute walk (0.4 mi) to the world-class dining and shopping of St. Armand’s Circle. LOCATION HIGHLIGHTS - Beach & Pool: Steps from Lido Beach and the Lido Pool Pavilion, featuring a heated public lap pool and beachside concessions. - St. Armand’s Circle: Walk to over 130 boutiques, galleries, and award-winning re.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Charming Lido Beach Retreat – Walk to Beach & St. Armand’s Circle! Escape to this beautifully updated 2-bedroom, 2-bath duplex in the heart of Lido Key, just minutes from Lido Beach (0.3 miles) and St. Armand’s Circle (0.4 miles). This modern home combines comfort, style, and convenience for the perfect beach getaway. This modern duplex offers the perfect blend of comfort, location, and style. Important to note: the property is elevated, with a flight of stairs leading to the front door. LOCATION HIGHLIGHTS: - Heart of Lido Key, Sarasota, Florida - 0.3 miles (6-minute walk) to Lido Bea.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Sunrise Cove! Accurately named, SUNRISE COVE offers incredible BAY sunrises morning after morning. This beautifully and recently updated two bedroom, 2 bath condo on the 3rd floor has gorgeous intracoastal water views and is only a 5 minute walk across the street to Turtle Beach. LOCATION HIGHLIGHTS: - Third-floor condo with stunning intracoastal water views - Just a 5-minute walk across the street to Turtle Beach - Short 10-minute drive or shuttle ride to Siesta Key Village shops, restaurants, cafes, and nightlife PROPERTY FEATURES: - Recently updated 2-bedroom, 2-bath condo (109.......

2 Bedrooms - 2 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Bay Tree Club Beach Side! Enjoy a 5-star stay at Bay Tree Club, a premier beach property on the south end of Siesta Key. This top-floor condo features two beautifully furnished bedrooms with ensuite baths, stunning Gulf views, and private beach access to both the Gulf of Mexico and Turtle Beach. Relax with sea breezes and spectacular scenery in one of Sarasota’s most desirable locations. LOCATION HIGHLIGHTS: - Located at Bay Tree Club on the south end of Siesta Key - Private beach on the Gulf of Mexico with direct access to Turtle Beach - Two communal pools and fishing pier - To.......

2 Bedrooms - 2 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Welcome to Kingston Arms 1st Floor! Simply paradise! This coveted end unit in Kingston Arms on Lido Key is just steps from St. Armand’s Circle and a few blocks from the pristine white sands of Lido Beach. Enjoy upscale shopping, dining, and nightly entertainment nearby, while still having a peaceful retreat surrounded by the clear, gentle waters of the Gulf of Mexico. LOCATION HIGHLIGHTS: - Walk to St. Armand’s Circle for high-end shopping, upscale dining, and nightly live entertainment - Just a few minutes walk to North Lido Beach & Park - Heated communal pool, BBQ grills - Just west of.......

2 Bedrooms - 2 Baths - Sleeps 5
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. WELCOME TO HOUSE OF THE SUN ON SIESTA KEY Experience the gold standard of island living at House of The Sun. Perched directly on the Gulf on the peaceful south end of Siesta Key, this second-floor retreat offers the perfect blend of modern luxury and classic beach fun. From the marble-clad rain shower to the "peek-a-boo" ocean views from your private balcony, every inch of this condo is designed for your relaxation. RESORT-STYLE AMENITIES - Beachfront Living: Step out of the complex and directly onto your private stretch of Siesta Key’s world-famous sands. - Gulf-Side Pool: Enjoy a dip in .......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.7 Star Review

. Welcome to Pelican Gardens Villa 23! Prime Lido Key location! This charming 1-bedroom, 2-bath villa is just steps from the heated community pool, a 7-minute walk to Lido Beach, and a 15-minute stroll to St. Armand’s Circle with its restaurants, shops, and nightlife. With convenient parking and a modern, cozy setup, it’s the perfect beach getaway. Unit has new furnishing: new pics to come! LOCATION HIGHLIGHTS - Across the street from the Gulf of Mexico - 7-minute walk to Lido Beach via Ritz Carlton pathway - 15-minute walk to St. Armand's Circle dining, shops, and nightlife - Steps to hea.......

1 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.8 Star Review

. Welcome to Hyland Hills at Heritage Oaks! Experience championship golf and tennis in a private gated community where you vacation like a member! Play on an 18-hole course redesigned by Ron Garl, enjoy practice facilities, weekly tournaments, and expert-led clinics, or hit the newly surfaced clay tennis courts with pro-led drills and leagues. Book today for the ultimate active getaway. See below for more info! LOCATION HIGHLIGHTS: - Private gated community just east of I-75 in Sarasota - 25 minutes to Siesta Key Beach, 20 minutes to Lido Key Beaches - Audubon-certified natural area spanning 5.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.8 Star Review

. WELCOME TO THE BEACH CLUB AT SIESTA KEY Experience the best of Siesta Key at The Beach Club, just steps from world-famous Crescent Beach with private gated access. Whether you’re here to relax by the Gulf, build sandcastles with family, or explore the vibrant local scene, this condo offers the perfect blend of comfort and convenience. LOCATION HIGHLIGHTS - Private gated access to Crescent Beach (shared with neighboring complexes) - Complimentary beach chairs and umbrellas on a first come, first served basis - Guest can set up in any unflagged area on the beach (close to the water line) - H.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Welcome to Kingston Arms 2nd Floor, Walk to Beach and St. Armand's! Simply paradise! This coveted end unit in Kingston Arms on Lido Key is just steps from St. Armand’s Circle and a short stroll from the pristine white sands of Lido Beach. Enjoy upscale shopping, dining, and nightly entertainment nearby, while still having a peaceful retreat surrounded by the clear, gentle waters of the Gulf. Just cross the Ringling Bridge and you’re in Downtown Sarasota, where dining, theater, and nightlife are at your fingertips. LOCATION HIGHLIGHTS: - Heated communal pool, BBQ grills - Walk to St. Arma.......

2 Bedrooms - 2 Baths - Sleeps 5
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Island Reef - Bayside With Private Beach! This beautiful 2-bedroom, 2-king suite unit in Island Reef on Siesta Key’s south end offers a private beach experience just across the street. Enjoy luxurious resort amenities including two heated pools, tennis/pickleball courts, docks, and a fishing pier, all with stunning Gulf and bay views. Watch incredible daily sunrises and sunsets for the ultimate relaxing getaway. Great monthly rental that allows you to bring your dog along! LOCATION HIGHLIGHTS: - South end of Siesta Key with private beach access just across the street - Stunning .......

2 Bedrooms - 2 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Welcome Yellow Pine Villa! Relax in a spacious, updated 2-bedroom villa just minutes from Siesta Key’s world-famous beaches. Nestled in a peaceful community surrounded by ponds, palms, and lush greenery, Yellow Pine Villa offers the perfect balance of resort-style amenities and a convenient Sarasota location. Crescent Beach Access #12 is only 3.7 miles away, and the heated community pool and spa are just steps from your door. LOCATION HIGHLIGHTS: - Heated community pool and tennis courts - Shuffleboard, practice putting green, and tanning deck - Access to community clubhouse with billiards.......

2 Bedrooms - 2 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Welcome to Siesta Sands Beach Resort Gulf View! New listing at Siesta Sands Beach Resort on the south end of Siesta Key, just steps from the Gulf of Mexico! This gated complex offers private beach access, two heated pools, and plenty of loungers for year-round relaxation. Enjoy endless beach fun—swim, fish, rent jet skis, build sandcastles, or simply soak up stunning sunsets with a good book. LOCATION HIGHLIGHTS: - South end of Siesta Key on the Gulf of Mexico - Gated beachfront complex with private beach & private access - Close to South Siesta Key Bridge for easy on/off access - Free shu.......

1 Bedrooms - 1 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Siesta Breakers on Crescent Beach! Escape to paradise on Siesta Key! This beautifully updated 2-bedroom, 2-bath condo at Siesta Breakers Beach Resort offers everything you need for a perfect Florida vacation. Nestled in a gated community with private access to Crescent Beach’s powdery white sand, this condo provides breathtaking Gulf and pool views, resort-style amenities, and a location that’s walking distance to shops, cafes, and activities. Whether you’re looking for relaxation or adventure, this condo is your gateway to an unforgettable stay. LOCATION HIGHLIGHTS: - Gated.......

2 Bedrooms - 2 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Pineapple Cove! Experience the best of Siesta Key at Pineapple Cove, a beautifully updated one-bedroom retreat on the vibrant south end of the island. Whether you’re here for a week of sun-drenched relaxation, a solo coastal getaway, or a small family beach break, this ground-floor condo puts you right where you want to be. LOCATION HIGHLIGHTS Skip the parking hassle! You are perfectly positioned for a car-free vacation: - Beach Access: A breezy 6-minute stroll to Crescent Beach (Access #12 & #13). - Nature’s Beauty: 7 minutes to the famous Point of Rocks for snorkeling and sc.......

1 Bedrooms - 1 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.5 Star Review

. Welcome to Kingston Arms on Lido Key 1 BR! This charming one-bedroom condo in the popular Kingston Arms complex offers courtyard and pool views, just 8 minutes from the famous white sands of Lido Beach and stunning Gulf sunsets. Steps from St. Armand’s Circle, enjoy cafés, shopping, fine dining, and nightly entertainment, all within walking distance. With an assigned covered parking spot and a second-floor location in an elevator building, it’s a peaceful and convenient beach getaway. LOCATION HIGHLIGHTS: - Heated communal pool, BBQ grills - Walk to St. Armand’s Circle for high-end sh.......

1 Bedrooms - 1 Baths - Sleeps 2
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.7 Star Review

. WELCOME TO THE BEACH CLUB AT SIESTA KEY Experience the best of Siesta Key at The Beach Club, just steps from world-famous Crescent Beach with private gated access. Whether you’re here to soak up the sun, enjoy powdery white sand, or take in unforgettable Gulf sunsets, this newly renovated condo offers the perfect setting for your beach getaway. LOCATION HIGHLIGHTS - Private gated access to Crescent Beach (shared with neighboring complexes) - Heated community pool with lush landscaping - Walking distance to restaurants, cafés, ice cream shops, and local boutiques - 10 minutes to Siesta Key.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.8 Star Review

. Welcome to Siesta Breakers Penthouse on the Beach! Experience Gulf views from this two-level penthouse at Siesta Breakers Beach Resort, complete with private access to world-famous Crescent Beach. Enjoy soft white sands, spectacular sunsets, and resort amenities including a heated pool, tennis courts, and BBQ area. With shops, cafés, and a free island shuttle nearby, everything Siesta Key offers is right at your fingertips. LOCATION HIGHLIGHTS: - Gated complex with private beach access - Heated Gulf-facing swimming pool - Two lighted tennis courts with BBQ grills nearby - Assigned covered p.......

3 Bedrooms - 4 Baths - Sleeps 8
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Siesta Breakers with Ocean Views, 5th Floor! Come stay in Siesta Breakers Beach Resort on Siesta Key's Crescent Beach for your next beach getaway! Siesta Breakers gated complex is on the beach, providing you with a private reserved beach area on famous Crescent Beach. RECENT UPGRADES We take guest feedback seriously! At the end of 2025, this unit has been recently updated with two major, top-of-the-line enhancements: - New Flooring: Both bedrooms now feature top-rated, easy-to-clean tile flooring (replacing all carpet mentioned in older reviews). - New Blinds: All five windows are.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Welcome to Yellow Pine Duplex Close to Pool! Book your next getaway in this newly renovated 2-bedroom villa just minutes from Siesta Key’s world-famous beaches. Located on the south side of Sarasota, this single-story duplex combines comfort, convenience, and resort-style amenities. Crescent Beach Access #12 is only 3.7 miles away, and the community’s heated pool and spa are just steps from your door. LOCATION HIGHLIGHTS: - Heated community pool and tennis courts - Shuffleboard, practice putting green, and tanning deck - Access to community clubhouse with billiards, library, and social r.......

2 Bedrooms - 2 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. Experience the best of Siesta Key at The Beach Club, just steps from world-famous Crescent Beach with private gated access. Whether you’re here to relax by the Gulf, build sandcastles with family, or explore the vibrant local scene, this condo offers the perfect blend of comfort and convenience. LOCATION HIGHLIGHTS - Private gated access to Crescent Beach (shared with neighboring complexes) - Complimentary beach chairs and umbrellas on a first come, first served basis - Guest can set up in any unflagged area on the beach (close to the water line) - Heated community pool with plenty of loun.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 5.0 Star Review

. Book your next beach vacation at Vista Hermosa in this gorgeous, updated 2-bedroom, 2-bath condo. Located on the 3rd floor with an elevator and no condo above you, this bright and comfortable unit is just a 6–7 minute walk to Public Beach Access #12 and #13 on Crescent Beach. Enjoy the ideal vacation spot on the southern side of Siesta Key, with restaurants, bars, ice cream shops, lunch spots, convenience stores, groceries, and specialty shops all nearby. Siesta Key Village is about a 10-minute drive or an easy ride on the free trolley. Vista Hermosa Condo Highlights Master Bedroom -King b.......

2 Bedrooms - 2 Baths - Sleeps 6
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. WELCOME TO PELICAN AT COASTAL BREEZE SIESTA Experience the best of bayfront living at Pelican, a charming second-floor unit in the Coastal Breeze Siesta 4-plex. With a private balcony overlooking Little Sarasota Bay, this cozy retreat offers the perfect blend of comfort, tranquility, and stunning views. Just a short walk to Turtle Beach, local restaurants, and the free Siesta Key Breeze Trolley, Pelican is your ideal Siesta Key escape. UNIT HIGHLIGHTS - Private balcony with panoramic bay views - Living room with queen sleeper sofa, Smart TV with YouTube TV, and sliding glass doors showcasing.......

1 Bedrooms - 1 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. WELCOME TO MANATEE AT COASTAL BREEZE SIESTA Discover the tranquility of Manatee at Coastal Breeze, a charming ground-floor unit in this waterfront 4-plex on Siesta Key. With direct access to the communal patio and stunning views of Little Sarasota Bay, this cozy retreat offers a peaceful bayfront escape while still being just a short walk to Turtle Beach, local dining, and the free Siesta Key Breeze Trolley. UNIT HIGHLIGHTS - Ground-floor unit with direct bay access from the living room - Living room with sliding glass doors to the bay, queen sofa sleeper, loveseat, coffee table, and Smart T.......

1 Bedrooms - 1 Baths - Sleeps 4
Vacation Rental in Sarasota

Vacation Rental in Sarasota 4.9 Star Review

. WELCOME TO TURTLE AT COASTAL BREEZE SIESTA Discover the peacefulness of Turtle at Coastal Breeze, a charming second-floor unit in the Coastal Breeze Siesta 4-plex. Just a 7-minute walk to Turtle Beach, this cozy retreat combines modern amenities with convenient access to all that Siesta Key has to offer. UNIT HIGHLIGHTS - Second-floor walk-up unit facing the street (no direct bay view). Inquire about water-view units if preferred - Bedroom with queen bed, partial bay view, and Smart TV with YouTube TV - Living room with queen sofa sleeper (currently being replaced) and Smart TV with YouTube .......

1 Bedrooms - 1 Baths - Sleeps 4
Vacation Rental in Sarasota