Vacation Condo Rentals By Owner In Siesta Key, FL

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWELCOME TO JAMAICA ROYALE BEACH VILLA brbr brbrRelaxation and fun await just steps from Siesta Key Beach! This charming one-bedroom villa combines modern comfort with unbeatable convenience. Guests enjoy three heated swimming pools, beautifully landscaped grounds, and a private walkway to Siesta Key’s famous white sand. brbr brbrPROPERTY HIGHLIGHTS brbrSleeps up to 6 guests with a king bed, queen bed, and queen sleeper sofa in the spacious living area brbrLess than a 5-minute walk to Siesta Key Beach via the complex’s private walkway brbrRecently renovated with new flooring, updated furnishings, and a modern kitchen with stainless steel appliances brbrPrivate patio with two dining tables, perfect for outdoor meals under the umbrella brbrIn-unit washer and dryer for added convenience brbrUncovered parking with one reserved space brbrBeautiful courtyard views from the villa brbr brbrSLEEPING ARRANGEMENTS brbrBedroom: King bed + Queen bed brbrLiving room: Queen sleeper sofa brbrAccommodates up to 6 guests brbr brbrINSIDE THE VILLA brbrSpacious open-plan living and dining area with updated furnishings brbrFully equipped kitchen with new cabinetry, stainless steel appliances, and cookware brbrPrivate laundry with washer and dryer brbrPatio dining area with seating for al fresco meals brbrKeyless entry for easy check-in brbr brbrRESORT AMENITIES brbrThree heated swimming pools, including one close to the Gulf brbrPrivate beach access with outdoor showers brbrTennis and shuffleboard courts brbrBBQ grilling areas brbrLandscaped walkways and gardens brbr brbrLOCATION brbrJust steps to Siesta Key Beach brbr1.5 miles to Siesta Key Village with shopping, dining, and live music brbrFree local ride services available for easy transportation around the island brbr brbrADDITIONAL DETAILS brbrNon-smoking and pet-free complex brbrBeach essentials provided, including towels, chairs, and accessories brbrPhotos reflect recent renovations; additional updates are ongoing to enhance guest stays brbrRepairs on the sliders are scheduled for May 13, 2026 between 9 - 11 am. brbr brbrEXTRA PERKS brbrComplimentary Xplorie activities for stays under 28 days, including bike rentals, dolphin cruises, kayak rentals, and admission to The Ringling Museum brbrOne complimentary round-trip airport transfer for up to 3 guests from SRQ or TPA with advance reservation (tips appreciated) brbr brbrBOOK YOUR STAY AT JAMAICA ROYALE BEACH VILLA TODAY brbr brbrEnjoy modern comfort, private beach access, and the perfect Siesta Key location for your next tropical getaway.brbrNext door complex is under construction. Unfortunately, we don't have any say in the matter.brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Hello, Sunshine! Jamaica Royale Condo: Steps to Private Beach, Pools, & Free Daily Activities!

Siesta Key, Florida, United States

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$452.0

- Kitchen includes large island with cook top stove and seating for four. br- Spacious living room with Ethan Allen furniture.br- Dining room seats four. br- Paneled den includes two couches and flat screen TV with sliding doors to balcony.br- Master Bedroom includes Ethan Allen king size bedroom set, flat screen TV, en suite bathroom with a walk in shower, walk in closet and sliding door to balcony.br- Bedroom #2 has a queen size bed, flat screen TV with a sliding door to balcony.br- Bedroom #3 has a queen size bed with sliding doors to balcony.br- Large heated pool, shuffleboard, workout room, private tennis courts which include pickle ball, boat docks with direct access to the intracoastal waterway. Private beach access just steps from Siesta Key beach. br- Coin-op washers and dryers are located on each end of every floor.br- Beach towels, toys, chairs, cooler, umbrellas and tennis rackets/balls provided.br- Reserved parking spot under building for two standard vehicles. Overflow parking available in front and back of building.

Newly renovated 2400 sq. ft (5th floor) condo w/ gulf views and 70 ft balcony

Siesta Key, Florida, United States

3

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Select Dates for Price

Gulf and Bay Club C204 by Tropical Sands AccommodationsbrCondo in Sarasota, FloridabrbrWelcome to Gulf and Bay Club C204! This beautiful two bedroom and two bath condo features a screened-in lanai with a dining table overlooking the condominiums lake, community pool, and you might just catch a glimpse of the Gulf of Mexico.brbrHighlights br• Private Beach Access br• Shared pools br• Tennis, pickleball, Racquetball, basketball, and shuffleboard courts br• Fitness Center br• Community electric vehicle chargers brbrInside is a gorgeous, fully equipped kitchen, a wicker and glass dining set, and a large sectional couch with a TV. The main bedroom is a true oasis of comfort, featuring a king-sized bed adorned with plush bedding and tropical decor. The attached bathroom is equally impressive, boasting two vanities, a walk-in shower, and a walk-in closet. The second bedroom is charmingly decorated with Florida-style furnishings and has easy access to the hall bath, which includes a shower and tub combo. To ensure your utmost convenience, each room has a television, and a washer and dryer are readily available for use.brbrGulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. This complex features three heated pools, saunas, a hot tub, activity courts for tennis, pickleball, racquetball, and shuffleboard, a fitness center, and numerous tiki-themed BBQ areas surrounding the lakes. Gulf & Bay Club C204 is a true gem and we cannot wait to have you as our guest and provide you and your loved ones with an incredible stay.

Gulf and Bay Club C204

Siesta Key, Florida, United States

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$191.65

2 bedroom updated condo at Vista Hermosa located on the quieter Southern end of Siesta Key. Just a short walk to the beach and all the Southern district community has to offer including great restaurants, clubs, bike & boat rentals, ice cream shop, drug store, market, deli, shopping and more! Hop on the free Siesta Key Breeze Trolley in front of the complex and explore the entire island including the Siesta Key Public Beach & Pavilion, Turtle Beach, and Siesta Key Village where you can wander around the shops and restaurants while listening to live music.brbrRelax in this comfortable 3rd floor condo just a short walk from Crescent Beach access #13. This unit is an upstairs corner unit, equipped with modern kitchen appliances, modern decor, spacious, and perfect for a party up to 5 people. You will find everything you need to make your stay comfortable in this unit, including all the kitchen essentials for those dinners indoors. There is a private lanai overlooking the pool that is completely screened in, giving you space to enjoy the outdoors without dealing with pesky mosquitoes! The condo features a King sized bed in the master bedroom, and a full size plus twin bed in the guest bedroom. The master bedroom has an ensuite bathroom with a walk in shower, and the guest bathroom has a tub/shower combo. brbrAll of your linens are supplied. TV's are in the living room & master bedroom, and free WiFi and cable are provided.brThe carport for this unit is located only a few feet from the elevator and parking is free. Laundry facilities are on each floor.br brEnjoy all of the on-site amenities Vista Hermosa has to offer including the heated pool, shuffleboard court, picnic tables for socializing, BBQ grills & a large clubhouse with a kitchen. Beach towels, beach chairs & coolers are all provided for your use.

Great Siesta Key Location! Short Walk to the Beach, Shopping & Dining and more! VH302B

Siesta Key, Florida, United States

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$174.35

Ideally located across the street from beach, the corner is the trolley stop, and less than1 mile walk via beach to village and Patriots Pier. newly renovated, 65 TV, Beach equipment, everything you'll want.

Idlewild South at Siesta Key, right across the st. from Siesta Beach Pavillion,

Siesta Key, Florida, United States

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$308.19

Beautifully renovated one bedroom King size super comfy mattress. Full bathroom with shower/tub. Fully remodeled kitchen with dishwasher. Living room has queen size memory foam sleeper sofa. Comfortably sleeps 4. Free parking, wi-fi, smart TVs in bed and living room. Heated pool, tiki hut on the bay, new charcoal grills, fishing pier/boat dock overlooking the bay. Cross the street to enjoy sandy white beach beaches just a 3 minute walk from condo. Beach cart, chairs and cooler provided.

Charm | Comfy | Tiki | Pool Private Beach

Siesta Key, Florida, United States

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$157.65

Spacious 2 bedroom, 2 bathroom condo at Excelsior Beach to Bay with large lanai overlooking the beautiful courtyard, pool & pond with fountain. Nicely furnished unit with plenty of room to stretch out and get comfortable. New living room furniture including pull out sofa bed. Washer & dryer are provided in the unit so you can pack light. Kitchen is well stocked and centrally located. Sleeps 6 comfortably with a king in the master, 2 twins in the guest bedroom & a sleeper sofa in the living room. Free WiFi & cable are provided, and unit has TV’s in both bedrooms. 2nd floor unit (first floor is the parking garage) and there is an elevator. About a 2 minute walk to the bay side heated pool.brbrEnjoy full access to all of the Gulf side amenities & the Bay side amenities that Excelsior has to offer. You will find 2 pristine heated pools (one on the bay side, and one on the gulf side), 2 jacuzzi, a bay side deck for fishing, tennis courts, pickle ball courts, shuffleboard, fitness room, library, BBQ grills & picnic areas PLUS a wide private area of our beautiful, world famous Siesta Key white-sand beach! Free beach loungers and umbrellas are already set up for your convenience on the beach.brbrHop on the FREE Siesta Key Breeze Trolley in front of the complex and ride to Siesta Key Village, Turtle Beach, and all points in between.brbrA minimum 2-week rental is required at Excelsior

Spacious Condo in a Great Location! Private Beach, 2 Pools, 2 Jaccuzi, Fishing Deck & More!

Siesta Key, Florida, United States

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$323.67

Welcome to your Siesta Key Turtle Beach Getaway! A highly sought-after retreat, this bright and airy condo offers the perfect blend of comfort, convenience, and resort-style relaxation. Nestled in the heart of Turtle Beach on Siesta Key, this inviting 2-bedroom, 2-bathroom retreat offers a fully equipped kitchen, a cozy living area, private balcony for relaxing as well as onsite resort-style amenities such as Pickle Ball, Shuffleboard, Fitness Center, Kayak Launch, and two heated pools for year-round enjoyment. brbrWhether you're here to relax on the white sandy beaches in the warm Florida sun with Gulf Coast breezes and gorgeous sunsets, explore the vibrant local attractions, or looking for a relaxing work-from-“anywhere” retreat - this family-friendly property promises a memorable stay! This unit offers everything you need to feel comfortable and at home while enjoying the beauty of Siesta Key. Perfect for couples, families, snowbirds, business travelers, or a beach getaway with friends. brbrThe Spacebr• Spacious, light-filled living area with coastal decor ideal for lounging and family gatherings after a day at the pool or beach and opens up to your private balconybr• A fully equipped kitchen perfect for preparing and sharing meals with your loved ones in the cozy dining room area br• Comfortable bedrooms with fresh hotel-style linens br• In-unit washer/dryer for your convenience br• Office space for remote workers br• Private balcony perfect for relaxing with a morning coffee or an evening cocktail while you enjoy Gulf Coast breezesbr• Covered parking for convenience, ease, and safetybr• Smart TV and high-speed internet accessbr• Clean plush bath towels provided and soft sand-resistant Turkish beach towels for you and your guestsbr• Starter vacation essentials provided for your stay including locally roasted coffee, soaps, shampoos, kitchen essentials, detergents and more! brbrResort-Style On-Site Amenitiesbr---------------------------brYour stay includes full access to an incredible list of amenities:brTwo heated swimming pools (one on the Bay and one on the Gulf) with loungersbrFitness CenterbrShuffleboard courtsbrTennis and Pickle Ball CourtsbrBoat Docks, Fishing Pier and Kayak LaunchbrGame Room, Library, and Billiards RoombrGrills and Outdoor Seating areas and PatiosbrBeach Access on the Gulf Coast brCar Wash AreasbrbrWhether you're visiting for world-famous beaches, boating, relaxation, or work-from-paradise life, this condo puts you in the ideal location on the quiet south end of Siesta Key.

Bay Views, Tennis, Heated Pools, Beach Access

Siesta Key, Florida, United States

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$283.19

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Siesta Bayside - Your Quiet Coastal Retreat! brbr brbrExperience the perfect island getaway in this spacious, ground-floor villa located in the prestigious gated community of Siesta Gulf & Bay Bayside. Offering the peace of no neighbors above you, this home is just a 5-minute stroll from your own private stretch of world-famous Siesta Key Beach. brbr brbrRESORT-STYLE AMENITIES brbr- Private Beach Access: Walk just 5 minutes to the gated beach entrance across the street. brbr- Active Lifestyle: Take your pick of two heated community pools or enjoy a match on the tennis courts. brbr- Waterfront Fun: Nearby Intracoastal access for fishing, boating, and sunrise views. brbr- Easy Travel: Use the free Siesta Key Trolley or local shuttle to explore the Village without worrying about parking. brbr brbrPROPERTY HIGHLIGHTS brbr- Quiet Ground-Floor Layout: No stairs and no upstairs neighbors for maximum privacy. brbr- Fresh Interiors: 1,200 sq. ft. featuring a modern kitchen with stainless appliances, breakfast bar, and a bright living area with floor-to-ceiling mirrors. brbr- Screened Lanai: The perfect spot to enjoy your morning coffee with fresh new cushions and a serene view. brbr- Modern Essentials: High-speed WiFi, cable TV in every room, and a private washer/dryer. brbr- 2026 Refresh: Newly updated with fresh paint, new lounge blinds, and high-efficiency Central AC to keep you perfectly cool. brbr brbrBEDROOMS & BATHROOMS brbr- Master Suite: King-size comfort with a large vanity and a private walk-in shower. brbr- Guest Bedroom: Perfect for families with both a Queen and a Twin bed. brbr- Extra Sleeping: The living room features a sleeper sofa, allowing the villa to accommodate up to 6 guests comfortably. brbr brbrEXTRA PERKS brbr- Beach Ready: Complimentary chairs, umbrella, and towels provided. brbr- Parking: Driveway parking included. Golf carts are welcome (must be stored in the garage or driveway). brbr brbrIMPORTANT INFO brbr- Amenity Access: Guests have full access to all Bayside amenities (2 pools, tennis, fishing) and the Private Beach Access. Please note that Gulf-side amenities (including the Gulf-side pool) are restricted to residents only. brbr- On-Site Registration: Per association rules, on-site check-in and parking passes are required for all guests. brbr- Parking & Garage: Driveway parking is provided. The garage is accessed weekly by staff for essential trash removal. brbr- Vehicle Restrictions: No boats, motorcycles, trailers, jet skis, or commercial/oversized vehicles are permitted. brbr- Golf Carts: Street-legal golf carts are allowed but must be stored in the garage or on the driveway. brbr brbrLOCAL FAVORITES brbr- The South End: Enjoy local staples like Clayton’s Grill, Miguel’s (for fine dining), Captain Curt’s (world-famous clam chowder), and the Orange Octopus for ice cream. brbr- The Village: Don't miss the Siesta Key Oyster Bar (SKOB), the Daiquiri Deck, or a classic breakfast at Another Broken Egg. brbr brbrBOOK YOUR STAY TODAY AND LET THE BEACH LIFE BEGIN!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.brbrParking passes: 1 parking pass is provided. There is a fee for extra parking passes.

Siesta Bayside: Quiet Ground-Floor Villa with Private Beach Access, Heated Pools, Tennis, & Fishing!

Siesta Key, Florida, United States

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$263.56

Midnight Cove II – Unit 133 by Tropical Sands Accommodationsbr1900 Cove II Place #133, Siesta Key FL 34242brbrWelcome to Midnight Cove II – Unit 133, a freshly renovated, spacious two bedroom, two bathroom coastal condo perfectly situated in the heart of Siesta Key. Located within the sought-after Midnight Cove II bayside community, this beautifully updated retreat offers a relaxing escape with easy access to Siesta Key Beach, Crescent Beach, and nearby dining and shopping in Siesta Village. With modern upgrades, comfortable furnishings, and resort-style amenities, this condo is ideal for families, couples, or small groups looking to unwind in paradise.brbrHighlightsbr• Freshly renovated condo in Midnight Cove IIbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 1 Full, 1 Twin, 1 Queen Sleeper Sofabr• Access to community pool, tennis courts, and private beach accessbr• Screened-in lanaibr• Fully equipped kitchenbr• Washer and dryerbr• Short walk or bike ride to Siesta Beach and Crescent Beachbr• 1 designated parking spacebr• Sleeps up to 6 guestsbrbrMidnight Cove II offers an array of exceptional amenities designed to elevate your Siesta Key vacation. Guests enjoy access to a heated community pool, tennis and pickleball courts, boat docks, grill stations, and beautifully landscaped pathways perfect for morning walks along the intracoastal waterway. Private beach access across the street provides an easy way to enjoy the world-famous quartz sand of Siesta Key Beach. After a day of sun and adventure, relax on your screened lanai with views of the lush tropical grounds.brbrStep inside to a bright, newly updated living space featuring coastal-inspired decor, comfortable seating, and a large TV for cozy evenings in. The open floor plan flows seamlessly into the dining area and a well-appointed kitchen equipped with full-size appliances, cookware, and everything needed to prepare meals with ease. Sliding glass doors open to the screened-in lanai, extending the living area and providing a peaceful spot for morning coffee or evening cocktails.brbrThe primary bedroom offers a plush king bed, an attached ensuite bathroom, a TV, and ample closet space, creating a restful retreat after a fun day on the island. The ensuite features a walk-in shower and updated vanity. The second bedroom includes a full bed and twin bed, ideal for kids or additional guests, and has access to a nearby full bathroom with a tub and shower combination.brA queen sleeper sofa in the living room provides additional accommodations, bringing the total occupancy to six.brbrRoom Detailsbr• Primary Bedroom: King Bed, TV, Closet, Ensuite Bathroom with Walk-In Showerbr• Bedroom 2: Full Bed + Twin Bed, TV, Hallway Bathroom Accessbr• Living Room: Queen Sleeper Sofabr• Bathroom 2: Full Bathroom with Tub/Shower CombobrbrThis condo also includes a washer and dryer, Wi-Fi, cable/streaming capabilities, community BBQ grills, and access to all Midnight Cove II amenities. With its prime location near Siesta Key Beach, restaurants, coffee shops, and watersport rentals, guests can easily enjoy the best of Siesta Key.brbrWith its fresh renovations, comfortable layout, and unbeatable location near the beaches of Siesta Key, Midnight Cove II – Unit 133 by Tropical Sands Accommodations offers the perfect setting for your next coastal escape. Book your stay today and enjoy the relaxed island lifestyle that keeps guests returning year after year.

Midnight Cove II – Unit 133

Siesta Key, Florida, United States

3

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Bath

Sleeps

$329.49

Jamaica Royale Unit 098 by Tropical Sands Accommodations brbrWelcome to Jamaica Royale Unit 098, a beautifully designed two-bedroom, two-bath villa in the heart of Siesta Key. Located within the sought-after Jamaica Royale community, this updated retreat is just a five-minute stroll from Siesta Beach, consistently ranked among the best beaches in the United States. Ideal for couples or small families, this home combines the comforts of modern living with the relaxed coastal charm that defines Sarasota’s Gulf Coast.brbrHighlightsbr• 5-minute walk to Siesta Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King bed, 2 Queen bedsbr• Private beach accessbr• 3 shared heated poolsbr• Community shuffleboard courtsbr• On-site laundry facilities + in-unit washer and dryerbr• 2 shared BBQ areasbr• 1 assigned parking spotbr• Convenient location near Siesta Key VillagebrbrSpend your days soaking up the sunshine at one of three sparkling community pools, including one with views of the Gulf of Mexico. Walk to the private beach access for a quiet day on the sand or enjoy a friendly game at the community shuffleboard courts. Outdoor BBQ areas are available for guest use, perfect for grilling dinner after a beach day. With pickleball and tennis courts within walking distance, you’ll have endless opportunities for recreation during your stay.brbrInside, a bright and open layout welcomes you with coastal decor and comfortable furnishings. The spacious living area features plush seating, a flat-screen TV, and large sliding doors that fill the space with natural light. The fully equipped kitchen includes modern appliances, cookware, and a regular drip coffeemaker, perfect for preparing breakfast before heading to the beach. Enjoy meals at the dining table or plan your next island adventure from this cheerful gathering space.brbrThe primary bedroom features a king-sized bed, elegant coastal accents, and a private ensuite bathroom with a shower and tub combination. The second bedroom offers two queen beds, ideal for family or friends, and shares access to a hallway bathroom with a modern walk-in shower.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with shower/tub combobr• Second Bedroom: Two Queen bedsbr• Second Bathroom: Hallway access with walk-in showerbrbrIn-unit washer and dryer, free Wi-Fi, community laundry facilities, beach chairs, and assigned parking are included for your convenience.brbrWith its unbeatable location, walkable access to Siesta Beach, and community amenities designed for relaxation, Jamaica Royale Unit 098 by Tropical Sands Accommodations is the perfect home base for your Sarasota getaway. Whether you’re here for a romantic retreat or a family vacation, your island adventure begins here, book your stay today and experience the best of Siesta Key living!

Jamaica Royale Unit 098-Newly renovated!

Siesta Key, Florida, United States

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$491.3

Welcome to Crescent arms unit CA605N Come spend a relaxing vacation in a true tropical paradise setting. You will soon see why Dr. Stephen P. Leatherman (Dr. Beach) has picked Siesta Key Beach as the #1 Beach in America more than once. With its four miles of pure white sand, it's ideal for sunbathing, walking, jogging, shelling, bicycling, or building your own sand castle. While not on the beach or perhaps enjoying other area attractions, my sixth floor gulf view condo is the perfect retreat. You will love the relaxing colors and decor. If you are looking for your vacation to be on the best beach and have the most beautiful sunsets, then you are in luck.brThe living room has a queen size sleeper sofa, double reclining love seat, and a rocker recliner. Both the master and guest bedrooms have their own full en-suite bathrooms, cable TV, ceiling fan and sliding glass door to the screened lanai. brThis unit Features :brBeach front property! Easy access on and off the Island! No loading up a car or crossing streets just walk out of the building onto the sand! 2 Bedroom 2 bathroom. Sleeps up to 6 people. Screened in lanai with patio furniture. Full kitchen, dining area, Tv in each room with free Wi-Fi. brShared resort amenities: brHeated pool. Private Beach. BBQ area with gas grills. Beach chairs provided. Beach personnel you can rent an umbrella from. Beach towels included. Bed linens and bath towels included. We do not have a linen service if you would like fresh linen you will have to wash them. Coin operated laundry in the tower buildings. Villas have washers and dryers in the garage.brNO GOLF CARTS, Trailers, motorcycles, mopeds, boats If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool, located directly on the beach side of Midnight Pass Road, we offer something for everyone: Wi-Fi, cable television, generous closet space, a lanai or glassed-in porch and a fully furnished kitchen. Crescent Arms features: Fully Furnished, Gated Condominiums Private Beach Access with Chairs No smoking and no pets, please!brThere is a seven-night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM We strongly encourage you to get rental insurance in case of any problems that may occur. Your Florida Vacation Awaits You.

Crescent Arms Vacation Rentals 605 N Siesta Key Florida

Siesta Key, Florida, United States

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$476.81

Light, bright, beachy and welcoming! A slice of old Florida just steps away from private beach access. Nestled behind the dunes is this hidden gem and slice of paradise. 2nd Fl unit with all the comforts of home, and recently updated with new paint, furniture, flooring, and ceiling fans. Spend your days at the #1 beach in the US or explore all there is to do in Siesta Key Village, Sarasota, St. Armand’s Circle, Lido key and Longboat Key.brbrBeach chairs are provided for our guests at the beach - Umbrellas, beach towels, beach wagon and cooler are in the unit. The community has a pool, shuffleboard and a Laundromat (located on ground floor). High speed internet, cable TV and smart TVs in all of the rooms. There is a charcoal grill located out front of the bldg, as well as common area table/umbrella space for hanging out. Full kitchen including a dishwasher and microwave for those nights you want to stay in, Keurig, as well as drip coffee makers (byo Kcups), and sheets and bath towels will be provided to our guests. brbrThere are 2 bedrooms, the first with a king bed, and the second with a queen and single bed.brbrThere is parking in front of the unit, but you can get around the Key using the Free Trolley system that runs from from 9:00 a.m til 10:00 p.m every 15 minutes. There are other free methods of transportation too that you can contact for pick-up (tips appreciated). And of course, Uber is always an option. Our unit is about 1.5 miles from the north Village and about 1 mile from the South Village. Very central location.

Bright & Beachy - Steps to the water!

Siesta Key, Florida, United States

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$315.93

Discover the latest addition to Crescent Royale's esteemed rental collection: Condo 5D, providing a coastal ambiance paired with vibrant aesthetics. This condo features a breathtaking panoramic beach view, offering a paradise-like experience. With 1,250 square feet of living space, this 2-bedroom, 2-bathroom unit accommodates up to four guests comfortably. brbrThis condo presents a sophisticated kitchen with exquisite quartz countertops, a luxurious king-sized bed in the master suite, and two charming twin beds in the secondary bedroom, combining style and comfort. brbrThe highlight is the stunning beach view visible from the lanai, showcasing a picturesque panorama of the sandy beaches and crystalline waters. Secure your ideal getaway by reserving Condo 5D for an unparalleled beach retreat. Act promptly, as this exquisite condo is expected to be highly sought after.brbrFor your beach enjoyment, we provide all the essentials you need - chairs, umbrellas, mats, and coolers! Moreover, Siesta Key Beach is conveniently close by, ensuring quick access to the sandy shores.brbrFurthermore, the Village is easily accessible via a complimentary trolley ride, offering a plethora of shopping, dining, and people-watching opportunities. Prepare for your beach paradise by packing your bags, gathering your companions, and anticipating a delightful stay. We eagerly await your arrival!brbrCrescent Royale boasts a variety of amenities for your pleasure, including a heated pool, fitness center, BBQ area, and shuffleboard. The onsite management team is dedicated to ensuring a seamless vacation experience. Don't hesitate - secure your stay at this highly sought-after Condo, a favorite among our guests.

Breathtaking Siesta Key Beach Gulf Views 2 Bed 2 Bath 100 Steps to Beach

Siesta Key, Florida, United States

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Sleeps

$224.73

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers Yacht & Racquet Club 4th Fl Pool & Bay Views End Unit! brbr brbrExperience elevated island living in this stunning 4th-floor corner retreat. As an end unit, this condo offers extra privacy, abundant natural light, and panoramic views of the resort pool and the sparkling Intracoastal waterway. Freshly renovated with sleek wood laminate flooring and a modern granite kitchen, this 3-bedroom sanctuary is perfectly designed for families, groups, or remote professionals looking for a work-from-paradise escape. Enjoy easy access to the beach via bike or Trolley and all the resort amenities Harbor Towers Yacht & Racquet Club offers. brbr brbrLOCATION HIGHLIGHTS: brbr- Direct bayfront setting in Harbor Towers on Siesta Key brbr- Less than 1 mile to famous Siesta Key Beach with powdery white sand brbr- Short bike ride or trolley ride to beach access brbr- Close to Siesta Key Village dining, shopping, and live music brbr- Resort-style gated community with sunrise bay views and marina scenery brbr- Two heated pools, three tennis courts brbr- Clubhouse with grilling stations, indoor/outdoor dining, pool table, large flat screen, and updated fitness room brbr brbrPROPERTY FEATURES: brbr- Renovated 3 bedroom/ 2 bathroom 4th floor condo (1566 sq ft) brbr- New wood laminate flooring throughout, ceramic tile in master ensuite brbr- Corner unit with views brbr- Private GE washer and dryer in unit brbr- One assigned covered parking space brbr- Cable and WiFi included brbr brbrLIVING ROOM: brbr- Comfortable seating area with updated décor brbr- Open layout connecting to kitchen and dining space brbr- Access to enclosed balcony brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with dishes, plates, bowls, Keurig and regular coffeemaker brbr- Open connection to dining and living areas for easy gatherings brbr- Dining table seats 6 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, work table, wall-mounted TV, access to enclosed balcony brbr- Master ensuite bathroom: separate vanity area, walk-in shower with glass doors brbr- Guest bedroom #1: queen bed, intracoastal views, work desk brbr- Guest bedroom #3: bunk bed (Twin over Queen), work desk, view of the water brbr- Guest bathroom: vanity, tub/shower combo, glass doors brbr brbrEXTRA PERKS: brbr- Beach gear including chairs, umbrella, and towels brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach with powder-white sand and turquoise water brbr- Siesta Key Village restaurants, bars, boutique shops, and nightlife brbr- Trolley rides to beach access points and local hotspots brbr brbrIMPORTANT INFO: brbr- No smoking inside the condo, hallways, or stairways brbr- No pets allowed brbr- Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed brbr brbrESCAPE THE EVERYDAY AND ENJOY THE VACATION YOU DESERVE. RESERVE YOUR SPOT NOW!brbrPlease note, each unit is only allowed 1 parking spot. brbr brbrStarting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). brbrCrane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding.brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Harbor Towers Yacht & Racquet Club Corner Suite: 4th Floor Bay & Pool Views & Great Workspaces

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$227.2

2 Heated Community Outdoor Pools | Large Sunroom w/ Desk & Dining Area | 7 Mi to Downtown Sarasota | 1,600 Sq FtbrbrHave fun in the Florida sun without leaving the gates at this Siesta Key vacation rental. This modern 2-bed, 2-bath condo in Peppertree Bay features great community amenities like on-site beach access, 2 heated outdoor pools, and a fitness center. Head out to shop at St. Armand’s Circle, try some local seafood at nearby restaurants, or rent jet skis at Siesta Key Watersports.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Sunroom: 1 queen Murphy bedbr- Living Room: 1 queen sleeper sofabrbrCOMMUNITY AMENITIESbr- Beach access, outdoor showerbr- 2 heated outdoor poolsbr- Grill pavilionbr- Fitness centerbr- Tennis courtsbr- Ping-pong tablebr- GatedbrbrCONDO LIVINGbr- Smart TVsbr- Sunroombr- Desk workspacebr- Dining table, breakfast barbr- En-suite bathroom, walk-in closetbr- Beach towels, snorkeling gearbrbrKITCHENbr- Stove/oven, refrigerator, dishwasher, microwavebr- Dishware/flatware, cooking basicsbr- Drip coffee maker, toasterbr- Starter trash bags & paper towelsbrbrGENERALbr- Free WiFibr- Central heating & A/C, ceiling fansbr- Washer/dryer, laundry detergent, iron/board, hangersbr- Linens/towels, hair dryerbr- Keyless entrybrbrACCESSIBILITYbr- Step-free access w/ elevatorbr- Single-story condobr- 3rd-floor unitbrbrPARKINGbr- Community garage (1 vehicle)br- Community lot (first-come, first-served)brbr-- THE LOCATION --brbr- On-site community beach accessbr- 1 mile to Siesta Beachbr- 7 miles to downtown Sarasota: Marie Selby Botanical Gardens Downtown Sarasota, Sarasota Opera House, Bayfront Park, Payne Park, McCurdy's Comedy Theatre, bars, restaurantsbr- 10 miles to St. Armands Circlebr- 1 mile to Siesta Key Watersportsbr- 12 miles to Sarasota Bradenton International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking of any kind allowed inside the home or anywhere on the propertybr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story condo on the 3rd floor offers step-free entry via the elevator

Walk to Beach: Resort-Style Siesta Key Condo!

Siesta Key, Florida, United States

Bed

Bath

8

Sleeps

$263.89

Escape to this beautifully furnished condo at Gulf and Bay Bayside, Professionally managed by Gulf Coast Vacation Rentals, where relaxation and convenience come together in the heart of Siesta Key. The expansive living area is perfect for unwinding after a day of exploration, while the lanai invites you to savor your morning coffee as you soak in the serene surroundings. Designed for comfort, the unit features a fully equipped kitchen, in-unit washer and dryer, and a private garage for added ease.brbrLocated within the Gulf and Bay Bayside community, guests are just a short stroll from beach access to Siesta Key's world-renowned white sandy beaches along the Gulf of Mexico. Spend your days lounging by the shore, combing for shells, or enjoying the vibrant turquoise waters. For a change of pace, explore the area's quaint shops, local dining, and outdoor activities, all just minutes away.brbrThis turnkey condo provides everything you need for a relaxing getaway in sunny Siesta Key. Whether you're planning a weekend retreat or an extended stay, this is the perfect home base to enjoy the beauty and charm of Florida's Gulf Coast. Start planning your Siesta Key escape today!brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Bayfront Siesta Key condo - 2 heated pools - tennis and pickleball - beach access - GBB 1351

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$243.74

Escape to the tranquil beauty of Siesta Key in this exquisite first-floor one-bedroom condominium at Gulf & Bay Bayside. Professionally managed by Gulf Coast Vacation Rentals, step into a realm of spaciousness and modern elegance, where every detail has been thoughtfully curated for your ultimate vacation retreat. From your private lanai, savor serene views of the bay and harbor, setting the perfect tone for relaxation.brbrThe recently renovated kitchen offers a fresh and inviting space, featuring contemporary cabinetry, updated lighting, stylish paint, and a practical kitchen work desk. Indulge in the spa-like bathroom, boasting a new, expansive walk-in shower with multiple shower heads, elegant new cabinetry, and sleek granite countertops. For your entertainment, the condo is equipped with three new flat-screen HDTVs and complimentary wireless internet access throughout.brbrConveniently situated within the Gulf & Bay Bayside community, this residence provides effortless access to exceptional amenities. The larger of the two heated swimming pools is just steps away, inviting you for a refreshing dip. The clubhouse offers a well-equipped exercise room and a relaxing sauna, perfect for unwinding after a day of exploring. Gather with friends and family at the conveniently located gas grills for an enjoyable outdoor meal.brbrBeyond the exceptional comforts of this condo, its prime location on Siesta Key offers unparalleled access to the island's renowned attractions. A leisurely stroll will lead you to the powdery white sands of Crescent Beach, consistently ranked among the world's finest. Immerse yourself in the crystal-clear waters of the Gulf of Mexico, perfect for swimming, sunbathing, and shelling. The vibrant Siesta Key Village, with its charming shops, diverse restaurants, and lively entertainment, is also within easy reach.brbrExperience the best of Siesta Key from this exceptional vacation rental at Gulf & Bay Bayside.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Bayfront Siesta Key condo with beach access - GBB1333

Siesta Key, Florida, United States

1

Bed

1

Bath

Sleeps

$289.06

Welcome to the epitome of waterfront luxury living in Siesta Key, Florida. Professionally managed by Gulf Coast Vacation Rentals, nestled within the prestigious Gulf and Bay Club Bayside, this first-floor condominium offers an unparalleled blend of comfort, style, and coastal charm.brbrAs you step through the front door, you're greeted by an airy and inviting open-concept living space adorned with tasteful coastal decor. The living area seamlessly flows into the dining space, creating the perfect setting for entertaining guests or enjoying quiet evenings with loved ones. Large windows allow natural light to flood the interior, while offering breathtaking views of the shimmering waters just beyond.brbrThe fully equipped kitchen boasts modern appliances, sleek cabinetry, and ample counter space, making meal preparation a delight. Whether you're whipping up a quick breakfast or preparing a gourmet dinner, this kitchen has everything you need to satisfy your culinary cravings.brbrThe primary bedroom is a sanctuary of comfort and relaxation, featuring a plush king-sized bed, ample closet space, and an en-suite bathroom complete with a luxurious walk-in shower. The second bedroom offers flexibility and convenience, with two twin beds that can easily accommodate family and loved ones. A second bathroom with a shower/tub combo ensures privacy and convenience for all occupants.brbrStep outside onto your private patio and prepare to be captivated by the stunning waterfront vistas that stretch as far as the eye can see. Whether you're enjoying al fresco dining, lounging with a good book, or simply soaking in the serene surroundings, this outdoor oasis is sure to be your favorite spot to unwind.brbrResidents of Gulf and Bay Club Bayside enjoy access to an array of resort-style amenities, including a clubhouse, fitness center, tennis courts, and multiple swimming pools. With direct access to the pristine beaches of Siesta Key just steps away, every day feels like a vacation in paradise.brbrHouse Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.

Bayfront Siesta Key condo - 2 heated pools - tennis and pickleball - beach access - GBB 1358

Siesta Key, Florida, United States

Bed