Condo Vacation Rentals in Sarasota, FL

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 - Perfect blend of seclusion and convenience - Indulge in the epitome of coastal living with this impeccably updated 2-bedroom, 2-bathroom condo nestled alongside the stunning shores of Crescent Beach. Welcome to paradise! This beautifully updated and tastefully furnished 2 bedroom, 2 bath condo is just steps away from Crescent Bea.......

4.6 Star Review

Welcome to your Siesta Key getaway! - Beautiful 2-bedroom, 2-bath condo for 6 guests - Renovated in May 2022 with modern finishes - Shared pool and hot tub for relaxation - Enclosed lanai with seating and Florida breeze - Fully equipped kitchen with new appliances - Essentials for families, including a pack ‘n play - Beach gear provided for your convenience - Short walk to Crescent Beach and local dining Once you parked you don't need to drive again. Perfectly located on Siesta Key, this beautiful 2-bedroom, 2-bath condo will surround you with everything Sarasota has to offer. Featuring s.......

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 -.......

4.9 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.......

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 -.......

5.0 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, - Just west of Down.......

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 .......

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 .......

4.7 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.......

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) .......

4.8 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 - Walk to St. Armandâ€.......

4.9 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 - Stunni.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 4
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. 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 billia.......

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 .......

4.9 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.......

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 .......

5.0 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 - Walk to St. Armand’s Circle for high-end sho.......

4.5 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 Siest.......

4.7 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.......

4.8 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.......

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 so.......

5.0 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 l.......

4.9 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 -Kin.......

5.0 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.......

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.......

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 .......

4.9 Star Review

. WELCOME TO DOLPHIN AT COASTAL BREEZE SIESTA Discover the charm of Siesta Key at Dolphin at Coastal Breeze, a cozy ground-level unit in the Coastal Breeze Siesta 4-plex. Just a 7-minute walk to Turtle Beach, this unit is perfect for couples or small groups looking for comfort, convenience, and easy access to all that Siesta Key has to offer. UNIT HIGHLIGHTS - Ground-level unit facing the street (quiet location, no bay view). For water view units, please inquire. - Bedroom with queen bed and Smart TV with YouTube TV (note: no bedroom door) - Living room with queen sofa sleeper and Smart TV wit.......

4.8 Star Review

. Welcome to Lulu’s Crescent Cottage #2~ Book this charming duplex on Siesta Key just a 5-minute walk from Crescent Beach. This updated retreat offers everything you need for a fabulous stay, plus a shared heated dipping pool. Whether you prefer relaxing on the soft white sands or filling your days with beach runs, jet skis, or fishing, your perfect getaway is waiting! LOCATION HIGHLIGHTS: - Located on Siesta Key, just a 5-minute walk to Crescent Beach Access #13 - Walkable to local favorites like Toasted Mango Café (8 minutes) and Big Water Fish Market (shorter walk) - Quick trolley r.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. Welcome Lulu's Crescent Cottage #1! Your perfect Siesta Key getaway awaits at LuLu’s Crescent, a charming standalone newly renovated duplex cottage just a 5-minute walk to Crescent Beach. This updated retreat features everything you need plus a shared heated dipping pool with the neighboring cottage. Relax under an umbrella, stroll the beach, or enjoy water adventures—paradise is waiting! LOCATION HIGHLIGHTS: - Located on Siesta Key, just a 5-minute walk to Crescent Beach Access #13 - Walkable to local favorites like Toasted Mango Café (8 minutes) and Big Water Fish Market (shor.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. Welcome to Kingston Arms 1st Floor Cottage! Come enjoy paradise! Newly renovated and furnished! Kingston Arms on Lido Key puts you just steps from the Gulf and St. Armand’s Circle, with its upscale shops, dining, and nightly entertainment. Enjoy the perfect balance of beach walks, nearby restaurants, and shopping, all while staying in a peaceful, convenient location just west of Downtown Sarasota. LOCATION HIGHLIGHTS: - Heated communal pool - Walk to St. Armand’s Circle for high-end shopping, upscale dining, and nightly live entertainment - Just a few minutes walk to North Lido Bea.......

4.7 Star Review

Immerse yourself in beachfront bliss at Lido Bliss: Imagine stepping off the elevator into your private sanctuary. Breathtaking panoramic views of the Gulf of Mexico greet you from your expansive balcony, setting the scene for an unforgettable stay. This meticulously kept, 4-bedroom 3.5 bath haven exudes luxury with Stunning views from Gulf to Bay showcasing the stunning scenery. Awaken your senses with the sophisticated coastal décor and unique light fixtures, creating a calming and inviting atmosphere. Indulge in gourmet meals in the well-equipped kitchen featuring a gas range, double ove.......

5.0 Star Review

Winter booking available. Ritz Carlton GOLD membership included. Enjoy convenience to Ritz managed amenities as you step off your private balcony "walk-down" onto the fire-pit and pool deck. This is the only condo in the entire building with this convenient feature. The building is premium as a Ritz Carlton-managed property! This like-new condo residence offers Travertine floors in the spacious main living areas. The Kitchen is designed for a true gourmet including a gas stove top. This beautiful home features motorized window treatments, a gas range, oven, an island, 1100 square foot terrace .......

0.0 Star Review

WELCOME TO COASTAL BREEZE SIESTA Your serene waterfront retreat on Siesta Key. This 4-unit property is perfect for large families or travel groups who want to stay close yet enjoy their own space. Set on tranquil Little Sarasota Bay and a short walk to Turtle Book the entire property and enjoy the best of both worlds—shared time together when you want it, privacy when you need it. LOCATION HIGHLIGHTS - Situated on Little Sarasota Bay with stunning water views and a peaceful setting - Just a short walk to Turtle Beach for sunbathing, swimming, and shell collecting - Shared boat dock availa.......

5.0 Star Review

This is a charming and luminous condo of 958 sq. ft. fully furnished with great taste. It will be perfect to enjoy your stay in Sarasota with an amazing water view! It features 1 bedroom, 1 den (a bedroom without a window), 1.5 bathroom, kitchen, and cozy living room with large sliding doors to the terrace. On the third floor of the brand new luxury residence (with an elevator). ★Living Area: Next you will find the very luminous living room. Large sliding windows let the light in and you can enjoy the beautiful view on the water and the bay to your left with the beautiful sunset! It featu.......

5.0 Star Review

2 Bedrooms - 1 Baths - Sleeps 4
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Timberwood Villa #183 Your Tranquil Sarasota Retreat Awaits! Welcome to Timberwood Villa, a peaceful hideaway nestled in a lush, resort-style community where nature, comfort, and convenience come together. Village Des Pins is a charming neighborhood set in a peaceful, park-like environment surrounded by lakes and pine trees. The community features an oversized heated pool, Jacuzzi, two lighted tennis courts, a basketball court, shuffleboard, a putting green, and a picnic area with grills. Whether you're planning beach days, cultural adventures, or simply relaxing in a serene setting, Timberwoo.......

0.0 Star Review

Spanish Pine Villa #210 A Serene Sarasota Escape Surrounded by Nature Welcome to Spanish Pine Villa, a peaceful retreat tucked within a lush, resort-style community in Sarasota. This charming villa offers a relaxed coastal lifestyle where comfort meets convenience, making it the perfect home base for your Florida getaway. Village Des Pins is a charming neighborhood set in a peaceful, park-like environment surrounded by lakes and pine trees. The community features an oversized heated pool, Jacuzzi, two lighted tennis courts, a basketball court, shuffleboard, a putting green, and a picnic area w.......

0.0 Star Review

Sarasota Sweets (Combined Villas) Your Tranquil Sarasota Retreat Awaits! Welcome to Sarasota Sweets, a pair of peaceful villas nestled within a lush, resort-style Sarasota community where nature, comfort, and convenience come together. Located in a pine tree forest, surrounded by tropical greenery, scenic ponds, and local wildlife, these charming single-level villas offer a serene setting perfect for slowing down and recharging. Whether you're planning beach days at the #1 Siesta Key Beach, cultural adventures, or simply relaxing in a calm, resort-like environment, Sarasota Sweets provides an .......

0.0 Star Review

. Welcome to Kingston Arms Modern 1 BR on the Lido! Welcome to your newly renovated one-bedroom condo in the heart of Lido Key! Located in the popular Kingston Arms Complex, this stylish retreat offers modern comforts, courtyard views, and an unbeatable location—just an 8-minute walk to North Lido Beach and steps from the lively St. Armands Circle, home to boutique shopping, fine dining, and entertainment. LOCATION HIGHLIGHTS: - Heated communal pool - Walk to St. Armand’s Circle for high-end shopping, upscale dining, and nightly live entertainment - Just a few minutes walk to North L.......

5.0 Star Review