Vacation Rentals By Owner In Siesta Key, FL

Summary:brbrWelcome to Endless Summer, a private Apartment “2nd Floor” right in the heart of the Siesta Village with the style, elegance, and charm of Siesta Key. Enjoy a family home that sleeps 7, a private heated pool, and quite literally in the heart of Siesta Village!brbrHidebrbrbrbrThe Space:brbrThis charming Siesta Key vacation rental home has all the amenities you could imagine at an absolutely UNBEATABLE location in the heart of Siesta Key Village! Enjoy being minutes away from world-famous Siesta Key Beach, voted the #1 beach in the USA! Combined with its sister property Sea la Vie, both units make up Oasis on the Key. Book Endless Summer for the ultimate beach escape!brbrbrbrEndless Summer can accommodate up to 8 guests with a bedding configuration as follows:brbrbrbr• Bedroom # 1: King Bed (1) - Sleeps: 2brbr• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbr• Bedroom # 3: Queen Bed (2) - Sleeps: 4brbrbrbrExclusive Amenities Include:brbrbrbr• Semi-Private Heated Pool (when combined with both units, the pool is private)brbr• Linens Providedbrbr• Kitchen Essentials Providedbrbr• Dining Areabrbr• Regular Coffee Makerbrbr• Flat Screen HDTVs (in living room + all bedrooms)brbr• Washer/Dryer (in unit)brbr• Beach Buggybrbr• Coolerbrbr• Beach Chairsbrbr• Gas Grill (Shared with Sea la Vie)brbr• Beach Towels brbr• Outdoor Lounge Areabrbr• Outdoor Showerbrbr• Parking on Propertybrbr• Free WiFibrbrbrbrGuest Access:brbrEntire second Floor /common areasbrbrbrbrThe Neighborhood:brbrSiesta Key, Florida is very proud of our sand. In fact, we have the “World’s Finest Whitest Sand”. You’ll find beautiful seashells on Siesta’s white sands, and you’ll find the finest beach-front vacation rentals and showcase homes on the Key, too. What else can you find on the sands of Siesta Key brbrbrbrYou are sure to see and hear our wild parrots and the friendly pelicans while you stroll the breathtaking 8-mile long barrier island that is Siesta Key. Siesta Village is famous for its wild parrots up in the swaying palm trees as well as many other shorebirds including terns, plovers, ibis, spoonbills, and storks. Bird watching is one of the favourite activities of residents and visitors alike. The many varieties of wading birds, like the beautiful snowy egret, and the great heron are just a few of the different types on our beaches and in our village. Keep an eye out for our 4 to 5 foot tall Florida Sand Hill Cranes with their bright red heads and distinctive calling sounds. You will often see two walking side by side since they mate for life. Our birds seem to live comfortably among the people of Siesta Key.brbrbrbrGetting Around:brbrGetting around Siesta Key is a breeze! While you're in the heart of Siesta Village, you'll find everything you need within walking distance, including the world-famous Siesta Key Beach. For those looking to explore further, the Sarasota-Bradenton International Airport (SRQ) is approximately a 20-minute drive away. Public transportation options are available, but a car is recommended for the most convenient exploration of the surrounding areas. Parking is available on the property, providing ease of access for your beach vacation.brbrbrbrOther Things to Note:brbrPlease note that this apartment is part of a duplex unit, potentially sharing outdoor spaces. Guests have access to beach essentials and free parking. Check-in is after 4:00 PM, and check-out is at 10:00 AM. The minimum age to rent is 22, and no smoking is allowed on the premises. Parties and events are strictly prohibited.brbrbrbrCancellation; Non-Refundable Transaction Fee VRBO BOOKING.COM ONLY In the event of any cancellation,or, or termination, of a booking for any reason whatsoever, the 3.9% transaction processing fee assessed at the time of payment shall be strictly non-refundable. This fee represents payment processing costs incurred and is earned immediately upon receipt of funds. Under no circumstances shall the 3.9% transaction fee be returned, credited, or otherwise reimbursed, including but not limited to cancellations made within any stated refund period, force majeure events, or cancellations initiated by the Guest. Any applicable refund shall be calculated net of the 3.9% transaction processing fee.brbrbrbrInteraction with Guests:brbrWe're here to ensure you have a fantastic stay! We're generally available throughout your visit to assist with any needs or questions you may have. The best way to reach us is via the message in the platform, where we aim to respond within a few hours. For urgent matters, please don't hesitate to send a message, and we'll do our best to assist you promptly. We're committed to making your stay as enjoyable and seamless as possible!

Siesta Key Village Retreat

Siesta Key, Florida, United States

Bed

Bath

7

Sleeps

$254.75

Nestled in Siesta Key, this lovely and recently remodeling house offers a perfect retreat for guests seeking comfort and convenience. With three bedrooms featuring a king, queen, and 2 twin , there’s plenty of space for everyone to relax. Two bathrooms include refreshing showers to make mornings easy. Guests can enjoy a pleasant stay with air conditioning to keep things cool and an iron for any last-minute touch-ups. Kitchen with many cooking utensils .brEnjoy pool (not heated ) back yard .sofa ,outdoor dining table brWhether you’re unwinding indoors or exploring nearby spots, this home provides a welcoming base. Enjoy all that Siesta Key has to offer when you stay at our place.

Private Vacation Home

3-bedroom house in Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$222.15

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers Gulf Luxe Escape! brbr brbrHarbor Towers Yacht and Racquet Club is a premier complex with loads of amenities that sits directly on the bay, overlooking the intracoastal waterway, where you can watch incredible morning sunrises. Close to famous Siesta Key beach (2 min. drive/15 min. walk) with its fabulous powdery white sands is just a short bike ride or Trolley ride away. Harbor Towers offers resort style amenities including 2 heated swimming pools, 3 clay tennis courts, and clubhouse with grilling station, exercise facility and sauna. brbr brbrLOCATION HIGHLIGHTS: brbr- Directly on the bay with intracoastal waterway views brbr- 2 min drive / 15 min walk to Siesta Key Beach brbr- Close to bike paths and trolley access brbr- Quiet, resort-style setting brbr brbrPROPERTY FEATURES: brbr- 3 bedroom/ 3 bathroom corner unit on the 3rd floor (1755 sq ft) brbr- Resort-style amenities: 2 heated swimming pools, 3 clay tennis courts, clubhouse with grilling station, exercise facility, and sauna brbr- 1 assigned parking spot brbr- Private washer and dryer combo, communal laundry room on each floor brbr- Dedicated WIFI and cable brbr brbrLIVING ROOM: brbr- L-shaped couch with access to the enclosed balcony brbr- Entertainment-ready with TV and cable brbr- Den room with queen sleeper sofa and TV brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen (appliances, cookware, dishes included) brbr- Dining space connected to living area brbr- Dining table seats 6 plus 4 more at the breakfast bar brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, TV with cable, closet space brbr- Master ensuite bathroom: separate vanity area, walk-in shower brbr- Guest bedroom #1: queen bed, view of the front of the complex, closet space brbr- Guest bathroom: vanity with tub/shower combo brbr- Guest bedroom #2: two twin beds, access via sliders to enclosed balcony brbr- Guest ensuite bathroom: vanity with tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbr- Famous Siesta Key Beach brbr- Nearby bike paths and trolley stops brbr- Local restaurants and shops a short ride away brbr brbrIMPORTANT INFO: brbr- Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed brbr- No smoking, no pets brbr brbrYOUR ULTIMATE BEACH VACATION STARTS HERE. BOOK YOUR STAY AND START UNWINDING THE MOMENT YOU ARRIVE!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.

Walk to Siesta Key Beach, 2 Heated Pools, Baby Pool, Tennis Courts, Fishing Piers, Updated Condo

Siesta Key, Florida, United States

Bed

Bath

7

Sleeps

$406.85

Stay, relax, and play—your Siesta Key escape starts here.brbrCreate lasting memories at this inviting townhouse just steps from the world-famous quartz sands of Crescent Beach. With private beach access and no roads to cross, enjoying the Gulf is safe, simple, and stress-free for the whole family.brbrUnwind in spacious, light-filled living areas, prepare meals in the fully equipped kitchen, and gather for games or movie nights after a day in the sun. This 2-bedroom retreat also features dedicated private parking and a prime beach location near local shops and dining. Hop on the free Siesta Key Breeze Trolley to explore the island with ease.brbrWhether you're here for beach days, sunsets, or laid-back island living, this is the perfect home base for your Siesta Key getaway.

Private Vacation Home

Siesta Key Beach Townhouse - Walk to Beach - 2BR - Pool & Parking

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$398.36

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrWelcome to your coastal escape at Island House Beach Resort, perfectly located on the widest part of Crescent Beach. This lovely 2-bedroom, 2-bathroom villa offers comfort, space, and privacy for a relaxing stay.brbrThe villa features a primary ensuite bedroom with a king-size bed, a guest bedroom with two double beds, and a spacious living and dining area that includes a sofa bed, making it ideal for families or groups.brbrEnjoy a beautifully updated, fully equipped kitchen with modern appliances, a screened lanai perfect for morning coffee or evening relaxation, and covered parking for your convenience. The villa also includes three large flat-screen TVs and central heating and air conditioning for year-round comfort.brbrExperience the best of Siesta Key living with the privacy of your own villa and the amenities of a beautifully maintained beachfront resort just steps from the powdery white sands and turquoise waters of the Gulf of Mexico.brbrbrJust a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Island House Beach Resort V9

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$407.76

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes a queen and full bed, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Island House Beach Resort V16

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$261.4

Your next vacation awaits in Siesta Key, Florida! This beachy 1-bath studio is the ideal Florida vacation rental for you and your significant other. Spend your days soaking up the sun on the beach nearby, hanging out by the pool area with a cold drink, or visiting Siesta Key Village where you’ll find shopping, dining, and bars. There’s also plenty to do nearby when you’ve had enough sun, including museums and botanical gardens! You’ll never be bored when you visit this Siesta Key beach rental.brbr-- THE PROPERTY --brbrSarasota VR Certification: CND6804981 | Beach Cooler & Towels | Shared Heated Pool | 1 Block to Siesta Key Village brbrStudio: Queen Bed, Twin Sleeper Sofa brbrOUTDOOR LIVING (shared w/ 2 other units): Heated pool w/ patio seating, outdoor shower, beach chairs, umbrellas, toys & 2 cartsbrSTUDIO LIVING: Smart TV, beachy interior, 2-person dining table, patio w/ outdoor seating brKITCHEN: Cooking basics, coffee maker, dishwasher, stove/oven, refrigerator, dishware & flatware, ice maker, microwave, toaster, blenderbrGENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, central heating & air conditioning, shared laundry machines, hair dryer, iron/board, trash bags & paper towelsbrFAQ: 1 exterior security camera (facing out), step-free access brPARKING: Shared parking lot (1 vehicle) brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, both with separate nightly rates: a 2-bedroom for 6 guests and a studio for 4 guests. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrLOCAL BEACHES: Sarasota Beach (0.3 miles), Crescent Beach (2 miles), Bayfront Park (6 miles)brSTATE PARKS: Oscar Scherer State Park (11 miles), Myakka River State Park (17 miles)brEXPLORE THE AREA: Siesta Key Village (0.1 miles), Marie Selby Botanical Gardens (5 miles), Sarasota Jungle Gardens (9 miles), Mote Marine Laboratory & Aquarium (10 miles), The John and Mable Ringling Museum of Art (10 miles)brAIRPORT: Sarasota Bradenton International Airport (10 miles)brbr-- 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 smokingbr- 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-inbr- NOTE: There are other bookable rentals on-site; other travelers may be present and share the driveway and some outdoor amenitiesbr- NOTE: Your safety matters. This property features 1 exterior security camera. This camera is located on the front entrance of the main house and faces the parking area. It actively records video and audio and will be turned on during your stay

Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$281.51

Plan the perfect beach vacation at this Florida vacation rental just steps away from the ocean. This 1-bathroom studio in Siesta Key, Florida, is surrounded by lush landscaping and palm trees to make you feel like you’re in paradise as soon as you arrive. Enjoy a fully equipped interior, shared pool, and provided beach gear so you can pack up and head to the beach whenever you want. Sunshine-loving families and friends can spend the day on the shore followed by an evening in Siesta Key Village!brbr-- THE PROPERTY --brbrBeach Cooler & Towels | Private Balcony | 0.3 Mi to Public BeachbrbrStudio: Queen Bed, Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play brbrOUTDOOR LIVING: (shared w/ 2 other units): Heated pool w/ patio seating, outdoor shower, beach chairs, umbrellas, toys & 2 cartsbrSTUDIO LIVING: Smart TV, beachy interior, 4-person dining tablebrKITCHEN: Cooking basics, coffee maker, dishwasher, stove/oven, refrigerator, dishware & flatware, ice maker, microwave, toaster, blenderbrGENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, central air conditioning, shared laundry machines, hair dryer, iron/board, trash bags & paper towelsbrFAQ: 1 exterior security camera (facing out), stairs required for access brPARKING: Shared parking lot (1 vehicle) brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, both with separate nightly rates: a 2-bedroom for 6 guests and a studio for 3 guests. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrLOCAL BEACHES: Sarasota Beach (0.3 miles), Crescent Beach (2 miles), Bayfront Park (6 miles)brSTATE PARKS: Oscar Scherer State Park (11 miles), Myakka River State Park (17 miles)brEXPLORE THE AREA: Siesta Key Village (0.1 miles), Marie Selby Botanical Gardens (5 miles), Sarasota Jungle Gardens (9 miles), Mote Marine Laboratory & Aquarium (10 miles), The John and Mable Ringling Museum of Art (10 miles)brAIRPORT: Sarasota Bradenton International Airport (10 miles)brbr-- 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 smokingbr- 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-inbr- NOTE: There are other bookable rentals on-site; other travelers may be present and share the driveway and some outdoor amenitiesbr- NOTE: Your safety matters. This property features 1 exterior security camera. This camera is located on the front entrance of the main house and faces the parking area. It actively records video and audio and will be turned on during your staybr- NOTE: This property is located on the second floor and requires stairs to access

Siesta Key Dream Inn Rental - Close to Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$237.03

Leona Breeze by Tropical Sands AccommodationsbrbrWelcome to Leona Breeze, the perfect home for long-term renters seeking a relaxed, comfortable stay on Siesta Key. Designed for extended stays, this two-story residence offers four bedrooms and two and a half bathrooms, providing the ideal backdrop for families, professionals, or groups looking to settle into a peaceful, Florida retreat. Located at the end of a quiet cul-de-sac, the home offers privacy and stunning canal-front views, just five minutes from Siesta Key Village’s shopping and dining, and a 13-minute walk to the renowned #1 beach in America.brbrHighlightsbr• 30-night minimum staybr• Dog friendly with approval and additional feebr• 13-minute walk to the beachbr• Canal frontbr• Large kitchenbr• Snowbird friendlybr• Water viewsbr• Two living areasbr• Laundry roombr• BBQ grillbrbrOutside, enjoy the tranquil, private backyard, perfect for unwinding or hosting friends. Sip morning coffee beside the canal or gather in the evening around the pool, your personal tropical oasis. Fish from your own backyard or simply relax in your serene surroundings.brbrInside, terrazzo floors and water views create a welcoming, serene atmosphere. The open-concept kitchen features stainless steel appliances and a large island, perfect for meal prep or casual entertaining. With two living areas, everyone has space to relax and unwind.brbrThe four bedrooms are thoughtfully furnished for comfort. The primary suite includes a queen bed and an ensuite bathroom with a walk-in shower. The other three bedrooms include three queen beds and a full bed, sharing a spacious hallway bathroom with a shower/tub combo, and a half bath rounds out the first floor.brbrRoom Detailsbr-Primary Bedroom, 2nd floor: Queen bed and ensuite bathroom with walk-in showerbr-Second Bedroom, 2nd floor: Queen bedbr-Third Bedroom, 2nd floor: Queen bedbr-Fourth Bedroom, 2nd floor: Full bedbrbrIf you’re searching for a laid-back, long-term Florida escape, Leona Breeze offers the comfort, privacy, and slice of paradise you’ve been dreaming of. Book now and settle into your ultimate Siesta Key retreat!brbr-brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company.brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Tropical Sands Accommodations Rental Policies for full details.brbrbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details.brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Private Vacation Home

Leona Breeze: Long Term Perfection!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$197.88

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers 3rd Fl 2 Bedroom! brbr brbrNewly furnished, new pics to come! brbr brbrEnjoy this condo that offers stunning bay views with incredible morning sunrises! Just a short drive, walk, or bike ride from Siesta Beach, its perfect for beach lovers. Enjoy resort-style amenities with the comfort of a cozy unit. brbr brbrLOCATION HIGHLIGHTS: brbr- Direct bayfront setting on the Intracoastal brbr- Quick 2–3 minute drive or 15-minute walk to Siesta Key Beach brbr- Trolley stop just outside the building brbr- Close to Siesta Key Village dining, shopping, and live music brbr- Resort-style community with marina views and sunrise scenery brbr- 2 heated swimming pools, 3 clay tennis courts brbr- Clubhouse with grilling station, exercise facility, and sauna brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom 3rd floor condo (1152 sq ft) brbr- Dedicated WIFI and cable brbr- Central AC with ceiling fans brbr- Screened-in balcony brbr- 1 assigned parking spot brbr- No area rugs brbr brbrLIVING ROOM: brbr- Comfy couch that doubles as a sofa bed brbr- Wall-mounted TV with cable brbr- Access via sliders to screened balcony brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with stainless steel appliances and double sinks brbr- Dining table seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, TV with cable, door access to balcony brbr- Master ensuite bathroom: spacious vanity with tub/shower combo brbr- Guest bedroom: queen bed, TV with cable, single twin rollout bed available upon request brbr- Guest bathroom: tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbrSiesta Key Beach with powder-white sand and turquoise water brbrSiesta Key Village restaurants, bars, and boutique shops brbrTrolley rides to the beach and village hotspots brbr brbrIMPORTANT INFO: brbr- Quiet hours enforced by the community brbr- No parties or smoking allowed. No pets brbr- Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed brbr brbrRELAX, UNWIND, AND LET YOUR PERFECT VACATION BEGIN - SECURE YOUR STAY TODAY!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.

Walk to Beach | Water View | Heated Pool plus Heated Baby Pool | Clay Tennis Courts

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$344.26

** BEACH FRONT WITH VIEWS** We did not get any damage to condo!!! December dates available at great rates!!! Complex did a great job cleaning up!! We are ready to rent Nov. 1st. come visit, you will not be disappointed!!brbr***Located Directly on Siesta Key Crescent Beach with White Sugary Sand***brJust a few steps and you are directly on the beach with free beach and lounge chairs.brbrBeach Gulf view from all rooms!!! Enjoy your morning coffee while looking at the beach and blue water with a delightful breeze, no better way to start your day!brbr This 5th floor two bedroom, two bath condo is totally and completely renovated. New tile throughout. There are two bedroom suites with private baths. It is a split floor plan so each suite is on different sides of condo for privacy. Each bedroom has new slider doors that open to screened in lanai with beautiful Gulf Views. Both rooms also has new furniture, mattresses and flat screen t.v.'s. Each bathroom is completely renovated with brand new walk in shower, new vanity, toilet, lighting. paint, ect. brOne bedroom has a King bed and 2nd bedroom has two queen beds to sleep 6 comfortably. brKitchen is brand new with new cabinets, granite counter tops and appliances. The kitchen is also completely stocked with everything that the cook might need to make your stay comfortable. All new cookware, glasses, flatware ect.brLiving room has beautiful new slider doors that open to lanai. Living room also new furniture, 55 flat screen t.v. with cable, and free wifi. brAll rooms have new ceiling fans, paint and new molding. brCondo is only a few steps to the #1 beach. Walk out of the building and put your feet in the white sugary sand of beautiful Siesta Key beach. Beach lounge chairs are supplied free of charge right in front of condo.brbrThere is also a very reasonable service at beach entrance where you can have umbrellas and chairs set up for you and ready for whenever you go to the beach.brbrGorgeous Gulf views from both bedrooms and living room. Lay in bed and open your eyes to a beautiful beach, blue water of the Gulf of Mexico!brbr Crescent Arms offers a picturesque pool that is secluded for your privacy and heated in winter for your comfort. The clubhouse, restrooms and showers are at the pool for your convenience. It is also a gated community and has one assigned parking spot with carport and visitor parking for extra cars. brbrClose to restaurants, stores, shopping, ice cream ect. A perfect place to spend a great vacation. Close walking distance to market, ice cream, restaurants, cafe, 7-11, tiki bar, Daiquiri Deck, famous Cap't Curts seafood. ect. brbrThere are also free jitneys and Trolley that will take you the length of the Key.brbrVery close to The Point of Rocks where people love to search for shells and go snorkeling. A perfect stay on this more private peaceful part of Famous Siesta Key Beach.brbrbr

Spectacular Beach View! Right on Beach! Amazing views!!

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$336.62

Gulf and Bay Club Unit A704 Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit A704, a bright and inviting two bedroom, two bathroom condo located in one of Siesta Key’s most sought-after beachfront communities. Perfect for extended stays, this 28-night minimum retreat places guests just a 5-minute walk from world-famous Siesta Beach, known for its powder-soft quartz sand and turquoise waters. With spacious interiors, serene paths, and an impressive collection of resort-style amenities, this condo is ideal for snowbirds, couples, or small families seeking comfort, convenience, and an elevated Siesta Key experience.brbrHighlightsbr• 5-minute walk to Siesta Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 1 Queenbr• Washer and dryer in unitbr• One assigned parking spotbr• Access to multiple shared poolsbr• Shared fitness center and spabr• Shared tennis and pickleball courtsbr• Gulf and Bay Club gated communitybrbrGuests at Gulf and Bay Club enjoy an exceptional lineup of resort-style community amenities designed to enhance long-term stays. Spend your afternoons relaxing by one of the heated shared pools, unwind in the shared in-ground spa, or enjoy a rejuvenating session at the fitness center. Active travelers will love the tennis courts, pickleball courts, and shuffleboard, while the shared cornhole area and clubhouse offer plenty of space for socializing. Beautifully maintained grounds, walking paths, and tropical landscaping create a peaceful atmosphere throughout your stay.brbrInside Unit A704, the open living area offers comfortable seating and large windows that fill the space with natural light. The fully equipped kitchen includes a refrigerator, stove, oven, dishwasher, microwave, toaster, and drip coffeemaker, making meal preparation simple and convenient. Enjoy casual breakfasts at the kitchen bar or gather at the dining table for relaxed evenings at home.brbrThe primary bedroom features a plush king bed, ample storage, and an ensuite bathroom, creating a private retreat after days spent exploring Siesta Key. The second bedroom offers a cozy queen bed and easy access to the shared hallway bathroom, making it perfect for visiting family or friends. Both bedrooms are designed for extended comfort with soothing coastal colors and space to settle in.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroombr• Second Bedroom: Queen bed, hallway bathroombrbrEnjoy the convenience of an in-unit washer and dryer, ideal for longer stays. The condo’s central Siesta Key location places guests close to Siesta Key Village, where you can enjoy waterfront dining, boutique shopping, coffee bars, and live entertainment. Whether you prefer relaxing beach days or exploring Sarasota’s arts and cultural scene, this home serves as a perfect home base.brbrWith its unbeatable location near Siesta Beach, comfortable two bedroom layout, and access to Gulf and Bay Club’s outstanding amenities, Gulf and Bay Club Unit A704 is the ideal Siesta Key escape for extended stays. Book your stay with Tropical Sands Accommodations and enjoy the coastal Florida lifestyle at its finest.

Gulf and Bay Club - A704

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$407.76

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twins beds and a sleeper sofa making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Island House Beach Resort V2

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$489.18

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a 2 Twin Size beds, along with a guest bedroom offering two twin beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Island House Beach Resort 8N

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$475.84

UPDATED PHOTOS COMING SOON!brbrThis beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, along with a guest bedroom offering two twin beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Island House Beach Resort 2N

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$412.79

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Island House Beach Resort V34

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$386.17

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Island House Beach Resort V29

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$436.95

Welcome to Jamaica Royale #203 – Beachside Comfort with a ViewbrSiesta Key, Florida | 2 Bed · 2 Bath · Sleeps 6brbrPerched on the second floor of Tower II in the exclusive, gated Jamaica Royale community, Unit #203 offers the perfect blend of coastal comfort and resort-style amenities—just steps from the world-renowned sands of Siesta Key Beach.brbrThis bright and inviting 2-bedroom, 2-bathroom condo features a king bed in the primary suite and two full beds in the second bedroom, ideal for families or couples traveling together. Enjoy beach views from your private lanai and relax with high-quality linens, bedding, and towels that ensure a restful stay.brbrThe fully stocked kitchen has everything you need for home-cooked meals, from morning coffee to seafood dinners. Step outside to find two large community pools, shared BBQ grills, and direct beach access complete with chairs, loungers, and umbrellas—both from the community and additional beach amenities provided in the unit.brbrOther conveniences include:brbrShared coin-operated laundry facilitiesbrSecure, gated complexbrPrivate beach area and lounge spacesbrDedicated Wi-Fi and streaming-ready TVsbrbrWhether you're looking for a week of sun-soaked relaxation or a work-from-beach getaway, Jamaica Royale #203 is your perfect island escape.brbrLocation Highlights:brJust minutes to Siesta Key Village, restaurants, shops, and watersport rentals.brbrWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. brbrBook now and enjoy one of the best beachfront values on Siesta Key!

Siesta Key Beachfront - 2BR Condo w/ Pools & Views

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$447.15

Location Location!! Spectacular views of the beach and water from our 5th-floor Penthouse condo suite with 3 King beds and new mattresses. Remodeled baths. Each day, enjoy our Magical Sunsets! The open floor plan is spacious and perfect for entertaining. The Living Room has plenty of seating. Beautifully decorated with a Leather sofa, love seat, Recliners, and a 75 Smart TV.brThis spacious and bright unit has a Renovated Kitchen with granite counters, a Microwave, and Stainless Steel Appliances. Staying calm and comfortable is easy, thanks to our unit's central air conditioning and ceiling fans in every room.brThe Main Bedroom suite features a king-size bed with a new comfort-top mattress, a Flat-Screen TV, a walk-in closet, and a remodeled bathroom. Imagine relaxing in bed, enjoying a view of the white-sand beach and the clear, sparkling waters of the Gulf of America. This is not a dream. It just feels like one!brBoth Guest suites have king-sized beds with new comfort mattresses, flat-screen TVs, and a private bathroom.br Amenities include a private gated beach, lounge chairs, a New Tiki Hut with Gas grills, tables, chairs, a lounge area—a picnic area with charcoal grills—and a heated pool with restrooms.brThe elevators are located in the middle of the building. Carts for carrying luggage are on the ground level next to the elevators. Coin-operated laundry is on each level by the elevators. There is assigned parking on the bottom level, with additional parking for guests with a permit from the office. brYou can't beat the location! Across the street from restaurants, ice cream, grocery stores, drug stores, pizza, a bakery, beach gear rentals, the post office, and 7-11...brWalk out your door onto the beach- no shoes needed! Warm crystal waters, tropical breezes, and the most inspiring sunsets await you in Siesta Key. So come to Siesta Key, calm your mind, and soothe your soul in paradise!

Spacious beachfront Penthouse 3 bed/3 bath suite, Stunning Gulf views!

Siesta Key, Florida, United States

Bed