Home Vacation Condo Rentals By Owner In Sarasota, FL

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$348.01

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Heated Pool, FREE WiFi, Luxury Bayside Condo Across from Siesta Key Beach | Gulf & Bay Club Bayside

Sarasota, Florida, United States

Escape to paradise at Gulf and Bay Club Bayside, a beautifully updated 3-bedroom, 2-bath waterfront condo located directly across from world-famous Siesta Key Beach. This spacious townhouse-style vacation rental combines Key West-inspired charm with resort-style amenities, making it the ideal choice for families, couples, snowbirds, and beach lovers seeking the ultimate Siesta Key getaway.brbrWake up to stunning Intracoastal Waterway views and enjoy a bright coastal interior designed for ...comfort and relaxation. The open-concept living space features an updated kitchen, spacious seating area, and peaceful waterfront scenery. The primary suite includes a King bed and private en-suite bathroom, while upstairs guests will enjoy a Queen bedroom and a third bedroom with two Full beds comfortably accommodating families and groups.brbrGuests love the unbeatable location just steps from private beach access to Siesta Key's famous white quartz sand beaches and crystal-clear Gulf waters. Spend your days swimming, shelling, paddleboarding, or enjoying the vibrant atmosphere near Siesta Key Public Beach.brbrBack at the resort community, enjoy:brbrTwo heated swimming poolsbrbrLighted tennis courtsbrbrFitness center and clubhousebrbrNew fishing and sunset dock on the IntracoastalbrbrPrivate garage for beach gear and bikesbrbrWaterfront walking paths and tropical landscapingbrbrLocated minutes from Siesta Key Village, you'll have easy access to local restaurants, live music, shopping, bars, bike rentals, kayaking, and free island trolley transportation.brbrWhy Guests Love This Siesta Key Vacation RentalbrbrWaterfront condo with bay viewsbrbrAcross the street from Siesta Key BeachbrbrPrivate beach accessbrbrFamily-friendly resort communitybrbrNear Siesta Key Village dining and nightlifebrbrIdeal for monthly stays and beach vacationsbrbrSpacious multi-level layout with garagebrbrClose to Sarasota attractions and boatingbrbrBook your Siesta Key beach vacation today and discover why guests return to Gulf & Bay Club Bayside year after year.brbrPlease note: This property is not pet friendly.brbrOur Cancellation Policy: In order to protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.
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$453.63

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Crystal Sands Tower Unit 311 - Beachfront

Sarasota, Florida, United States

Enjoy a luxurious vacation in this spacious, completely renovated two bedroom, two bath high rise condo with spectacular view of the Gulf of Mexico and Crescent Beach. This unit has a new king size Tempur-Pedic pressure relieving Swedish mattress in the master bedroom. The living room has a 37 HDTV and a Human TOUCH Robotic Massage recliner. Relax on the screened lanai with a soft breeze and the sound of the gentle waves.brbrThe near by, glass enclosed elevator provides a view of beautiful Siesta Key while you come and go to your private covered parking space.brbrSiesta Key is famous for beautiful turquoise water full of sea life and white powdery crystal sand beaches. Enjoy all our unique features with the convenience of being steps from our own private beach or relax in one of our two heated swimming pools.brbrEach room has lanai access and expansive beachfront views from the living room and both bedrooms. You can enjoy waking up to a fresh cup of coffee as you listen to waves roll in from offshore or unwind at the end of each day sipping your favorite glass of wine as the sun sets in the Gulf of Mexico. You will never miss a sunset! Indulge from the comfort of your own condo!brbrOur Accommodations are just 2 miles from the popular Siesta Key Village with shops, restaurants, bars, coffee shops and more or a short walk to nearby restaurants, convenience stores, and water sports rentals!brbrIf you are looking for a family vacation or a romantic getaway Crystal Sands is the perfect place for you. Come stay with us at the most exclusive resort on Siesta Key that offers the best beachfront views on the island!br
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Exceptional(9)

$855.62

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Siesta Key Beach Penthouse Miles of Gulf and Beach Views Large 4 Bed 3 Bath

Sarasota, Florida, United States

The Penhouse at Crescent Royale Condominiums. Welcome to the Star of The Show - where paradise meets luxury! Presenting Unit 7A - a double-wide penthouse, recently spruced up to perfection, with four spacious bedrooms and three and a half bathrooms, sprawling over 2,000 square feet. From its seventh-floor location, this property offers a spectacular view of the beach, with ample living and entertainment space, perfect for hosting family and friends while enjoying panoramic views of the beach.brbrThe two master bedrooms are fit for royalty, each with a stunning beach view, private bathroom, and ample storage. One of the guest bedrooms flaunts a view of the gulf, while the other provides a stunning vista of the pool area and the northern island.brbrDesigned with entertainment in mind, this unit features top-of-the-line Viking appliances, custom cherry wood cabinets, granite countertops, a cooking island, and an entertainment island that doubles as a bar or gathering spot for family and friends. The exquisite furnishings and fixtures are impressive, but the real showstopper is the uninterrupted, stunning view of the Gulf of Mexico and Siesta Key beach, voted America's number one beach in 2025.brbrThe expansive double-wide lanai is a sight to behold, offering mesmerizing views of the beach and allowing you to see forever. The glass sliding doors and screens of the lanai provide flexibility in opening up the space to the tropical breezes or closing it off to expand the air-conditioned living area.brbrWhile enjoying the beach view from the property is an unmatched experience, walking out onto the beach is an adventure in itself. Siesta Key beach boasts of the softest and whitest sand in the world, like powdery baby dust. You can walk for miles in either direction or simply relax, soaking up the sun and the gentle sounds of the surf. The beach is easily accessible, with 100 steps away from the beach. brbrThis penthouse offers a rare combination of luxurious living, entertainment, breathtaking views, and beach access, making it the ultimate dream destination for anyone looking for the ultimate beach lifestyle.
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$678.68

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Bayfront Siesta Key condo with two pools, pickleball and tennis, and beach access - GBB 1371

Sarasota, Florida, United States

Welcome to paradise at Gulf & Bay Club Bayside in Siesta Key, Florida! Professionally managed by Gulf Coast Vacation Rentals. This exquisite first-floor condo offers the epitome of coastal living with two bedrooms, two bathrooms, and a bay front setting that will take your breath away. Immerse yourself in the tranquil ambiance as you step into the spacious living area, adorned with tasteful decor and flooded with natural light. The fully-equipped kitchen boasts modern amenities, perfect for culinary enthusiasts.brbrRelax and unwind in the comfort of two beautifully appointed bedrooms, each offering a private retreat. The primary bedroom features an en-suite bathroom, ensuring convenience and privacy. Step outside onto the private patio to witness awe-inspiring sunsets over the bay, creating the idyllic moment.brbrGulf & Bay Club Bayside provides exclusive access to a host of amenities, including pristine beaches, sparkling pools, and lush tropical landscapes. With Siesta Key's renowned white sandy beaches just moments away, this bay front condo offers a perfect blend of luxury, convenience, and stunning views—a true haven for those seeking the ultimate Florida Gulf Coast experience.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.
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$427.89

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Siesta Key! Walk to the bars and restaurants. Rent a boat! Go Fishing! You can even bring your boat!

Sarasota, Florida, United States

***AVAILABLE January through April 30th 2025. Welcome to the Beach! Prime Siesta Key location. This large, spacious 2 Bedroom/2 Bath split floor plan condo comes with a full-length balcony with views of the gulf and intracoastal waterway, as well as the beautiful sunsets.brbrAvailable as a monthly rental, the interior boasts a decorative fireplace, reclining sofa, two walk-in closets, washer and dryer in laundry room its coined operated at the end of the hall. Walk-in shower in master. Cable, Wi-Fi, internet. The building also has a fitness center, his and hers saunas, additional laundry on every floor.brbrThis condo comes with a carport with plenty of additional parking. The Anchorage offers every beach amenity you could want. Deeded beach access, heated olympic size pool, three lighted tennis courts, beautiful grounds in a park-like setting leading to the intracoastal. Prime location to watch the parade of boats going by. Grilling and picnic area.brbrFree boat docking. Wi-Fi throughout property. Best of all is the location! Easy on, easy off of Stickney Point Bridge. Boat rentals, great restaurants and bars and shops right across the street, and you can take the free Siesta Key Trolley anywhere from Turtle Beach to Siesta Key Village. No need to get in your car, just enjoy your beach vacation with everything right there!
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$370.15

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Steps away from the #1 beach! Spectacular views on the GIANT balcony!

Sarasota, Florida, United States

Jamaica Royale's private BEACH FRONT community is just steps away from the soft white quartz sand of Siesta Key Beach which has been voted #1 beach in the USA year after year! Enjoy beach, pool and sunsets from the huge balcony (like no other on the key) of this 4th floor, beautifully decorated with a coastal look, two bedroom, two bath unit. Granite counter tops in the spacious and fully equipped kitchen, washer/dryer, and three flat screen TVs. Jamaica Royale has three heated freshwater pools, one of which overlooks the beach. This unit is spotless and has absolutely everything you will need to enjoy a relaxing vacation on the beach. brbr- Beach Chairs & Beach Toys In The Unitbr- Beach Chairs Provided By Jamaica Royale At No Extra Chargebr- All Bath Towels & Bed Linensbr- 6 Beach Towels includedbr- Free Reserved Parking Spacebr- Gas Grills (2)br- Outdoor Showerbr- Three Heated Fresh Water Pools With Picnic Tables & Umbrellasbr- Elevatorbr- Bike Rackbr- Short Beach Walk To Siesta Key Public Beachbr -Siesta Key Public Beach offers: br - Tennis Courts, Playground, Concessions, Seasonal EventsbrbrThis condo is located just one mile away from Siesta Key Village where there is entertainment, restaurants, shopping, and night life. Several free transportation options are available to and from Siesta Key Village so a car is not necessary. brbrNo smoking or no pets.brbrMonthly guests welcome.brbrMust be 25 years or older to rent.brbrSpeedy WiFi.
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Exceptional(10)

$280.16

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Gorgeous Bay View, WiFi/Cable, Walk to Beach, 2 Heated Pools, Tennis/Pickleball | Updated Baths!

Sarasota, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Sunrise Cove! brbr brbrAccurately 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. brbr brbrLOCATION HIGHLIGHTS: brbr- Third-floor condo with stunning intracoastal water views brbr- Just a 5-minute walk across the street to Turtle Beach brbr- Short 10-minute drive or shuttle ride to Siesta Key Village shops, restaurants, cafes, and nightlife brbr brbrPROPERTY FEATURES: brbr- Recently updated 2-bedroom, 2-bath condo (1093 sq ft) brbr- Basic cable and WiFi included brbr- Balcony with sliding doors and A/C brbr- Carport parking available brbr- Heated swimming pool, lighted tennis/pickleball courts brbr- BBQ grills, clubhouse with fitness room, billiards, ping pong, and game/reading room brbr- Free communal laundry on each floor brbr brbrLIVING ROOM: brbr- Open layout connecting to balcony brbr- Comfortable seating for relaxing brbr- Access to A/C and natural light from sliding doors brbr brbrKITCHEN AND DINING: brbr- Fully stocked with basic cookware and utensils brbr- Space for casual dining and meal prep brbr- Adjacent to living area for easy entertaining brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Bedroom: Queen bed, TV, basic cable brbr- Second Bedroom: Two twin beds brbr- Two full bathrooms: master has shower/rub combo, guest has walk-in shower brbr brbrEXTRA PERKS: brbr- Beach accessories included for guest use: couple of chairs, an umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- Short drive or shuttle to Siesta Key Village restaurants, cafes, shops, and nightlife brbr- Easy access to Turtle Beach for sun, sand, and water activities brbr brbrIMPORTANT INFO brbr- Monthly rental property; HOA application and approval required brbr- No smoking brbr- No pets allowed on property or in unit brbr- Vehicle restrictions may apply; check before booking (boats, motorcycles, trailers, jet skis, golf carts, oversized/commercial vehicles) brbr brbrMAKE THE BEACH YOUR ESCAPE—SECURE YOUR STAY NOWbrbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.
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Exceptional(4)

$417.03

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2 Bedroom Condo at Crescent Arms Steps from the Beach!

Sarasota, Florida, United States

This lovely 2 bedroom - 2 bath, Crescent Arms condo, sleeps up to 6. Positioned on the north side, on the third floor in the south tower, it has a partial view of the powder white sands and the azure waters of the Gulf. Fully furnished and decorated, this condo features a large living room, dining area and two large bedrooms. The beautiful screened in Lanai can be accessed from sliders in the living room as well as both bedrooms. Located directly on world famous Crescent Beach, this condo is perfect for relaxing on the beach, or taking the short walk to the South Village. Crescent Arms offers a picturesque serpentine pool that is secluded for your privacy and heated in winter for your comfort. The clubhouse, restrooms and showers are near the pool for your convenience. Just bring your sunscreen, bathing suit, flip-flops, and enjoy your island get-away vacation!brbrBedroom 1: KingbrBedroom 2: 2 QueensbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbrPlease Note: Golf Cart, Motorcycles, Mopeds, RVS, trailers, boats or anything besides a car/ truck are NOT allowed on property grounds.br*Security authorization Hold taken upon check-in. Amount: $1,000
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$358.64

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Horizons West #111 on Siesta Key is a 1 Bedroom Unit with a View of the Gulf of Mexico

Sarasota, Florida, United States

Unit 111 is an oversized 1 bedroom hi-rise, beachfront unit in Horizon West, Siesta Key Florida. Recently updated open-floor plan unit with gorgeous views of the Gulf of Mexico and beautiful Crescent Beach.br br Just steps from your front door and you are at the beautiful beachfront salt water pool and hot tub. Another few steps to the luxurious soft quartz white sand of Crescent Beach. Walking on the sand feels like walking on powder or flour.br It is truly exquisite and is one of the top attractions of the island and draws tourists from around the world. Siesta Key's Crescent Beach has been voted #1 Beach in the United States. Complimentary cabanas, loungers and chairs are provided beachside for Horizon West owners and guests. Two deluxe grills and picnic tables are located beachside between the gulf and the pool for outdoor meals with gorgeous sunset views. Siesta Key especially likes to show off at sunset, a must see!br br After all the sun and fresh salt-air, your family can relax in a comfy unit with a King bed and Queen sleeper sofa, updated luxurious bathroom, large screen TV and high-speed internet and Wi-Fi. Washer and dryer are located right across the hall as you open the door from this unit ready for your use if necessary. br br Siesta Key fun is just getting started when the sun goes down. A quick trip on the Siesta Key Trolley or one of the many free taxi services to the charming Siesta Key Village. Both North and South Village are known for their restaurants, shopping, and entertainment. Breakfast, lunch, dinner, coffee, ice cream or cocktails, the village has everything you need. From quaint souvenir stores to luxurious boutiques, fine dining to sports bars, Siesta Key villages have something for everyone. For the early birds, grab a hot cup of coffee from the unit's Keurig, and head down to watch the peaceful sunrise and admire the local residents; birds having their morning staff meeting, dolphins playing in the gulf, and pelicans fishing. All in a day at Horizon West, Siesta Key!br br *IF MAKING AN INQUIRY AFTER 5:00 p. m. , YOU WILL BE CONTACTED THE NEXT MORNING BY AN HORIZONS WEST AGENT. IF OVER THE WEEKEND, AN HORIZONS WEST AGENT WILL RESPOND TO YOU ON MONDAY.br Amenities Include:br - Gulf Side: Yesbr - Bed Size MBR: Kingbr - # of Baths: 1br - Gulf View: Yesbr - Conf Line 1: Beautiful, updatedbr - Conf line 2: unit w/gulf view!br - Conf Line 3: Has Internet access.
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Exceptional(72)

$349.1

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Gulf Waters-Beach Club at Siesta Key 108D by RVA

Sarasota, Florida, United States

RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, whitest sand beach in the world.” This new resort features modern decor, mixed with the youthful attitude of this world-famous destination, making this chic resort one of the most desired accommodations on Siesta Key. Decorated using clean lines and bright colors, all while remaining inviting and engaging, this resort includes all that is signature to Southwest Florida. Each unit features a full-size kitchen, large flat-screen TV, modern decor, Avonite countertops, and top-of-the-line Four Seasons.brbrbrbrYour vacation in Southwest Florida doesn’t stop there; Siesta Key is the perfect spot for a young family or the young-at-heart. This barrier island is energized – with plenty of Frisbee throwing, volleyball, jogging, beachside tennis, biking and picnicking. The Siesta Village offers a spirited combination of different sides of Sarasota, from candlelit dining to beach boutiques and cool daiquiris. Best of all, you can laze away the afternoon and partake in a “siesta” in the sun, either swaying on your favorite raft above the gentle waves or on the beach near the lapping shoreline. For luxurious accommodations on Siesta Key, the only choice is The Beach Club.brbrbrbrAccommodations: The Beach Club at Siesta Key offers studio, one- or two-bedroom units, just steps from the beautiful beaches. Relax by the heated community pool or stroll through nearby Siesta Key Village, where cuisine and entertainment take on an island flair.brbrbrbrUnit #108D Features: 2-bedroom, 2-bathroom unit in building D which faces the community poolbrbrbrbrBedding: 2 Queens, Sleeper SofabrbrbrbrBeach Access: The Beach Club at Siesta Key offers convenient beach access to the world-famous Siesta Key sand just across the street from our property. Access is steps away thru a shared community gate; the code to the gate is provided upon arrival. For those looking to experience more - the Siesta Key public beach is a short 2 mile drive from the resort and includes a snack bar, tennis courts, a playground, picnic and grilling areas, a weekly drum circle and more.brbrbrbrResort Features: Beach Access Footsteps Away, Heated Swimming Pool, Hot Tub, On-site Office, Private or Community Patios, Complimentary Wireless Internet Access, Full-size Kitchens, Avonite Countertops, Stainless Steel Appliances, LCD Flat-Screen TV's, Private Washer/Dryer, Ideal Siesta Key LocationbrbrbrbrHousekeeping Note: This resort is a self-service environment, however daily maid service is available upon request for an additional fee.
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