Home Vacation Rentals By Owner In Siesta Key, FL

Showing 1840 Of 2077 Vacation Rentals
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$193.41

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Condo

Harbor Towers 401 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Harbor Towers 401 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers 401, a beautifully positioned one-bedroom, one-bath Siesta Key vacation rental located in the gated Harbor Towers Yacht and Racquet Club on Midnight Pass Road. Perched on an upper floor with sweeping tropical and water views, this inviting residence offers a private balcony, open living space, and resort style amenities, all just minutes from Crescent Beach. With a 13-night minimum stay requirement, this condo is ideal for extended island getaways and seasonal retreats.brbrHighlightsbr• 1 Bedroom / 1 Bathroombr• King bedbr• Sleeper sofa in living roombr• Private balcony with panoramic viewsbr• 13-night minimum stay communitybr• Gated waterfront propertybr• Two heated poolsbr• Three Har-Tru tennis courtsbr• 40-slip marina on the Intracoastal Waterwaybr• Fitness center and saunabrbrHarbor Towers is one of the most desirable waterfront communities on Siesta Key, known for its upscale atmosphere and loyal returning guests. This gated property features two heated pools surrounded by tropical landscaping, three Har-Tru tennis courts, and a 40-slip marina along the Intracoastal Waterway. Guests also enjoy access to a fitness center and sauna, creating a true resort style experience ideal for snowbirds and longer stays.brbrUnit 401’s private balcony offers the perfect place to enjoy morning coffee or evening sunsets while overlooking lush palms, sparkling waters, and the beautifully maintained grounds. The open concept living area is bright and comfortable, with plush seating and large windows that frame stunning views. Sliding glass doors lead directly to the private balcony, allowing natural light and coastal breezes to fill the space. A sleeper sofa in the living room provides additional accommodations, making this condo a great option for couples or small groups.brbrThe fully equipped kitchen features granite countertops, stainless steel appliances, and ample prep space, flowing seamlessly into the dining and living areas. Whether preparing meals at home or enjoying takeout from Siesta Key Village, the layout makes gathering easy and comfortable. brbrThe primary bedroom features a king bed, ceiling fan, and private access to the balcony, allowing you to wake up to soft coastal light and tranquil views. Designed for comfort, the bedroom offers generous storage and a peaceful atmosphere for extended stays. The full hallway bathroom includes modern finishes and a spacious shower, conveniently located near both the bedroom and main living area.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Living Room: Sleeper sofabr• Hallway Bathroom: Full bath with showerbrbrHarbor Towers 401 is located in a 13-night minimum stay community, creating a relaxed, residential environment ideal for extended vacations. The complex is conveniently located near Crescent Beach and a short drive to Siesta Key Village dining, shopping, and entertainment.brbrIf you are searching for a Siesta Key condo rental with breathtaking views, a private balcony, and access to resort style waterfront amenities, Harbor Towers 401 by Tropical Sands Accommodations is the perfect extended island escape. Enjoy the pools, tennis courts, marina, and relaxed coastal lifestyle that bring guests back to Harbor Towers year after year. Book your stay today and experience elevated Siesta Key living.
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Sleep 4

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$215.63

/ Nightly
Condo

Harbor Towers 125 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Harbor Towers 125 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers 125, a spacious two-bedroom, two-bath Siesta Key vacation rental located in the gated Harbor Towers Yacht and Racquet Club on Midnight Pass Road. Perfect for extended island getaways with a 13-night minimum stay, this inviting condo offers a bright open layout, private outdoor patio space, and access to one of the most sought-after waterfront communities near Crescent Beach.brbrHighlightsbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 2 Full bedsbr• Private patio with outdoor diningbr• In-unit washer and dryerbr• 13-night minimum stay communitybr• Gated waterfront propertybr• Two heated poolsbr• Three Har-Tru tennis courtsbr• 40-slip marina on the Intracoastal Waterwaybr• Fitness center and saunabrbrHarbor Towers is known for its upscale atmosphere and loyal seasonal guests who return year after year. This gated waterfront community offers two heated pools surrounded by tropical landscaping, three Har-Tru tennis courts, and a 40-slip marina along the Intracoastal Waterway. Guests also enjoy access to a fitness center and sauna, creating a true resort style setting ideal for snowbirds and longer Siesta Key stays.brbrUnit 125 features a private patio with outdoor seating and dining, perfect for enjoying morning coffee under bright Florida skies or relaxing after a day at Siesta Key Beach. The open concept living and dining area is bright and welcoming, with comfortable leather seating, coastal decor, and sliding glass doors that allow natural light to fill the space. The living room offers a large television and ample seating, making it easy to unwind after beach days or evenings out on the island.brbrThe fully equipped kitchen features granite countertops, stainless steel appliances, crisp white cabinetry, and everything needed to prepare meals during your stay. The dining table with wicker seating provides a charming coastal touch and a comfortable space for shared meals or game nights.brbrThe primary bedroom offers a king bed, soft coastal tones, and a private ensuite bathroom with a spacious walk-in shower. This relaxing retreat is designed for comfort and privacy during longer stays. The second bedroom features two full beds, making it an excellent option for families, visiting guests, or friends traveling together. A full hallway bathroom with updated finishes is conveniently located near the guest bedroom and main living area. Both bedrooms include ceiling fans, comfortable bedding, and ample storage to make extended stays feel effortless.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with walk-in showerbr• Second Bedroom: Two Full bedsbr• Hallway Bathroom: Full bath with showerbrbrUnit 125 includes an in unit washer and dryer for added convenience during extended stays. The 13-night minimum stay requirement creates a quieter, more residential environment throughout the complex, making Harbor Towers especially appealing for seasonal guests.brbrLocated near Crescent Beach and just a short drive to Siesta Key Village dining and shopping, Harbor Towers places you in the heart of island living while maintaining a peaceful waterfront setting.brbrIf you are searching for a comfortable and well located Siesta Key condo rental with resort style amenities and flexible sleeping arrangements, Harbor Towers 125 by Tropical Sands Accommodations is an excellent choice. Enjoy the pools, tennis courts, marina views, and relaxed coastal atmosphere that make Harbor Towers a returning guest favorite. Book your extended stay today and experience the best of Siesta Key living.
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Bath 2

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Sleep 6

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$242.47

/ Nightly
Condo

Harbor Towers 121 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Harbor Towers 121 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers 121, a beautifully updated two-bedroom, two-bath Siesta Key vacation rental located in the gated Harbor Towers Yacht and Racquet Club on Midnight Pass Road. Designed for extended stays with a 14-night minimum, this stylish residence features a sleek modern kitchen, two king bedrooms, and a spacious private terrace, all within one of Siesta Key’s most desirable waterfront communities near Crescent Beach.brbrHighlightsbr• 2 Bedrooms / 2 Bathroomsbr• 2 King bedsbr• Private terrace with outdoor seatingbr• In unit washer and dryerbr• Modern renovated kitchenbr• 13-night minimum stay communitybr• Gated waterfront propertybr• Two heated poolsbr• Three Har-Tru tennis courtsbr• 40-slip marina on the Intracoastal WaterwaybrbrHarbor Towers is known for its upscale atmosphere and loyal returning guests who come back season after season. This gated waterfront community offers two heated pools surrounded by tropical landscaping, three Har-Tru tennis courts, and a 40-slip marina along the Intracoastal Waterway. A fitness center and sauna add to the resort style experience, making this an ideal choice for snowbirds and extended island stays.brbrAfter a morning at Crescent Beach, unwind on your private terrace overlooking swaying palms and coastal sunshine, or enjoy an afternoon by the pool just steps from your building.brbrUnit 121 welcomes you with a bright, modern interior featuring clean lines, warm wood finishes, and polished tile flooring throughout. The open living area offers comfortable seating and a large television, creating the perfect place to relax after a day exploring Siesta Key. The fully renovated kitchen stands out with warm wood cabinetry, stainless steel appliances, sleek countertops, and everything needed to prepare meals during your stay. The dining area sits just off the kitchen, offering an inviting space for shared dinners, morning coffee, or planning the next beach day.brFloor to ceiling sliding doors fill the living space with natural light and provide seamless access to the private terrace, enhancing the indoor-outdoor Florida lifestyle.brbrThe primary bedroom features a king bed, modern furnishings, and a private ensuite bathroom with updated finishes and a spacious walk-in shower. This peaceful retreat offers comfort and privacy for extended stays. The second bedroom also includes a king bed, making this layout ideal for two couples or guests seeking equal sleeping accommodations. A full hallway bathroom with updated vanity and shower provides convenient access for the guest bedroom and main living area. Both bedrooms are designed for comfort with ample storage, ceiling fans, and calming coastal tones that enhance the relaxed island atmosphere.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with walk-in showerbr• Second Bedroom: King bedbr• Hallway Bathroom: Full bath with showerbrbrThis residence includes an in unit washer and dryer, ideal for longer stays. The 14-night minimum stay requirement creates a quieter, more residential feel brthroughout the community, perfect for guests seeking a peaceful Siesta Key retreat.brbrHarbor Towers is conveniently located near Crescent Beach, Siesta Key Beach, local dining, and shopping along Midnight Pass Road, offering easy access to everything the island has to offer.brbrIf you are looking for a refined Siesta Key condo rental with resort-style amenities, two king suites, and a private terrace in a gated waterfront community, Harbor Towers 121 by Tropical Sands Accommodations delivers the perfect extended island escape. Enjoy the pools, tennis courts, marina views, and relaxed coastal lifestyle that make Harbor Towers a guest favorite year after year. Secure your dates today and settle into the best of Siesta Key living.
Bed 2

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Bath 2

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Sleep 6

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Exceptional(11)

$363.17

/ Nightly
Condo

Fresh & updated 2/2 Siesta Key Condo~Fast WiFi, Pool, Private beach access!

Siesta Key, Florida, United States

Welcome to ! Kick off your shoes, grab a drink, and enjoy the palm view (our condo’s namesake!) from this beautifully updated garden view unit.brbrOur condo isn’t directly beachfront, but the - with over 400 feet of private beach front — just a quick two-minute walk from the front door. In the evenings, head to the spacious sundeck or grab a beach chair and enjoy one of Siesta Key’s unforgettable sunsets.brbrThis - , - is conveniently located on the 2nd floor near the west end of Building 1. Access is easy via stairs or elevator, and both the pool and beach are just steps away.brbr• : King bed in the primary, two twins in the second bedroom, plus a sleeper sofa in the living roombr• : Fully equipped with granite countertops, modern appliances, and all the essentialsbr ️ br • All furniture has been replaced since 2021br • Kitchen items, décor, and fresh paint (2022)br • Bathrooms fully remodeled + all-new flooring (2023)br • New lanai sliders, windows, and front door (2025)brbrWe’re constantly improving — fixing what’s broken, replacing what’s missing, and refreshing what’s dated — so your stay is comfortable and worry-free.brbr is consistently ranked among the top beaches in the U.S.! Siesta Dunes provides beach chairs on a first-come basis, and we’ve stocked the condo with — chairs, umbrella, cooler, wagon, and beach toys.brbrCome enjoy our comfortable condo and the welcoming amenities Siesta Dunes has to offer. brbr ️ br• Private Beach accessbr• Beach Side & Garden Grills (rear of the building as well as on the sundeck)br• Beach Deck & Pavilionbr• Tennis / Pickleball Courtbr• Saltwater heated pool & Hot Tub (community/resort)br• Beach Chairs and Loungesbr• Club housebr• Shared Laundry facilities (onsite) - (shared/card operated, just down the hall on same level as condo)brbr❤️ brPalm View isn’t a corporate-managed rental — it’s a privately owned condo, rented and self-managed by our family. We work closely with the on-site rental team and are constantly updating, refreshing, and upgrading based on guest feedback. Our hands-on approach ensures a clean, comfortable, and affordable experience that feels like home.brbrCompare Palm View to other condos of similar size — we think you’ll notice the difference right away.brbr br• Roof replacement for our building and the clubhouse are scheduled to begin May 4, 2026br• Security deposit, ID verification, and signed rental agreement requiredbr• Cameras are located throughout the Siesta Dunes property for security (none inside units)br• Refunds are not provided for illness, weather, or other uncontrollable events — travel insurance is strongly encouragedbr• In the event of a named storm, refunds or reschedules are considered only if the property is within an official mandatory evacuation zone per the National Hurricane Center
Bed 2

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Bath 2

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Sleep 6

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Exceptional(13)

$465.75

/ Nightly
Condo

Stunning Siesta Key Beach Views from 2 Bedroom Condo!

Siesta Key, Florida, United States

Stunning Updated Condo with Spectacular Siesta Key Beach Views! Our House At The Beach! Enjoy panoramic views of the Gulf and Siesta Key Beach, to fantastic sunsets and downtown Sarasota, all from 12 floor-to-ceiling sliding doors that open onto 2 huge balconies. Full gulf facing corner unit on the 6th floor, accessible by stairs or elevator, and just a short 1–2 minute walk to the beach! The master bedroom has a picture window looking out over the beach and ocean and the guest room looks over the pool and island. This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis courts and a covered pavilion with grilling area. Right across the street is our world-famous Siesta Beach, and just minutes away is Siesta Key Village, offering endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! brbrBedroom 1- KingbrBedroom 2- Two Full BedsbrLiving Room- Queen Sleeper SofabrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $1,000
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Bath 2

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Exceptional(1)

$795.46

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Private Vacation Home

Pineapple Palms: Pool+Hot Tub, 5 min to Beach

Siesta Key, Florida, United States

Welcome to Pineapple Palms, your tropical getaway in beautiful Siesta Key. With space for up to 10 guests, this 4-bedroom home features an open layout made for gathering, a private heated pool, hot tub, and inviting indoor spaces where everyone can unwind after a day in the sun.brbrJust minutes from the powdery white sands of Siesta Beach, this cozy, updated space is perfect for a laid-back getaway. Comfort, island vibes, and the perfect location—everything you need for a memorable stay.brbrThe Spacebr• Sleeps up to 10 guestsbr• 4 bedrooms, 2 bathroomsbr• Spacious one-level layoutbr• Private heated poolbr• Hot tubbr• Cozy movie roombr• Large family dining roombr• Open kitchen perfect for entertainingbr• Propane grillbr• Smart TVsbr• High-speed Wi-FibrbrWhere You'll Sleepbr• 2 King bedsbr• 2 Queen bedsbr• Additional sofa bed in the movie roombrThe primary king suite is a peaceful retreat featuring a large walk-in shower and soaking bathtub, perfect for unwinding after a day at the beach.brbrFully Equipped KitchenbrWhether you’re preparing breakfast before the beach or dinner for the group, the kitchen is stocked with essentials and ready for your stay.brbrIncluded for guest use:brPots and pans, cooking utensils, plates, cups, and dining essentials, cooking range with oven, microwave, dishwasher, toaster, blender, coffee maker, and Keurig machine with coffee pods providedbrbrPrime LocationbrLocated just 5 minutes from Siesta Beach and Siesta Village, you’ll be close to world-famous white sand beaches, restaurants, shops, nightlife, and island activities.brbrDog Friendlybr• No cats allowed due to property restrictionsbr• Must be disclosed at the time of bookingbr• $100 pet fee per dog, per staybr• Maximum of 2 dogs unless approved in advancebrbrGood to Knowbr• Quiet hours begin at 10 PMbr• This is a residential neighborhood, so we ask guests to be respectful of neighborsbr• Routine pool or lawn maintenance may occasionally occur during your staybrbrYour Siesta Key Escape AwaitsbrSpend your days at the beach, your evenings by the pool, and your nights relaxing with family and friends. Whether you’re here for adventure or downtime, Pineapple Palms is the perfect home base for your Siesta Key vacation.brbrBook your stay today and start making memories.
Bed 5

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Bath 2

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Sleep 10

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Exceptional(1)

$385.66

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Condo

Upscale Penthouse Condo in the heart of Siesta Key - Penthouse Paradise

Siesta Key, Florida, United States

Penthouse Paradise by Siesta Key Luxury Rental Properties brbrPenthouse Paradise is a spacious three-bedroom, three-and-a-half-bathroom penthouse condo perched on the 6th floor of a premier building in the heart of Siesta Key. Located just a short walk from the world-renowned white sands of Siesta Key Beach, this upscale residence offers panoramic balcony views, an open and airy layout, and all the comforts of a luxurious extended stay. Designed for relaxation and convenience, this home is ideal for families, couples traveling together, or guests seeking a month-long retreat to paradise.brbr________________________________________brHighlightsbr• VIEWS! VIEWS! VIEWS!br• Luxury 6th-Floor Penthouse Condo with Multiple Balconiesbr• Elevator Opens Directly Into Penthousebr• Walking Distance to Siesta Key Beachbr• Walk to Shops and Restaurantsbr• Pet-Friendly Propertybr• Beach Chairs and Beach Cart Includedbr• Dedicated Workspacebr• HUGE Walk-in Closetsbr• Ensuite Jacuzzi Garden Tubbr• 30-Night Minimum Stay Required January - Aprilbr• Shorter Stays Available May – DecemberbrbrThis exceptional penthouse boasts sweeping views from every angle, thanks to its elevated location and multiple private balconies – one attached to each bedroom, creating seamless indoor-outdoor living. Soak in stunning sunrises and sunsets, enjoy morning coffee in the sea breeze, or dine alfresco with island views. With a beach cart and chairs provided, your days in the sun are easy and carefree. With an in-unit washer and dryer, keeping up with sandy swimsuits or extended stays is effortless. Whether you’re here for work, play, or rest, you’ll find everything you need for a laid-back island lifestyle.brbrStep into a bright, beautifully appointed open-concept living area with coastal-chic furnishings, oversized windows, and sliding glass doors that flood the space with natural light. Kick back on the plush sofa and stream your favorite shows on the smart TV, or gather for cocktails with sunset views from the balcony. The adjacent dining area offers seating for six, while the large kitchen island makes meal prep a breeze. The fully equipped kitchen features stainless steel appliances, ample counter space, and everything needed to prepare meals for the entire group.brbrThe spacious primary suite is a serene retreat with a king-sized bed, private balcony access, and an enormous walk-in closet. The ensuite bathroom includes a luxurious standalone soaking tub, a walk-in glass shower, and dual vanities. The second bedroom features a queen bed, shared balcony, and an ensuite bath with a shower/tub combo—perfect for guests who enjoy a long soak after the beach. The third bedroom also offers a queen bed, private balcony, and an ensuite bathroom with a sleek walk-in shower. A convenient half bathroom is located off the main living space for added guest comfort.brbrRoom Detailsbr• Primary Bedroom: King Bed, Balcony, Ensuite Bathroom, Walk-In Shower + Soaking Tubbr• Second Bedroom: Queen Bed, Balcony, Ensuite Bathroom, Shower/Tub Combobr• Third Bedroom: Queen Bed, Balcony, Ensuite Bathroom, Walk-In ShowerbrbrFrom your prime location on Old Stickney Point Road, you're just minutes from iconic Siesta Key Beach – the only lifeguard-protected stretch of sand on the island, featuring picnic tables, shaded areas, food stands, restrooms, and large public parking. Explore nearby shops, local seafood restaurants, beach bars, and watersports rentals within walking distance. With its unbeatable combination of comfort, convenience, and coastal beauty, Penthouse Paradise is your perfect home away from home on Florida’s Gulf Coast.brbrWhether you’re planning a seasonal getaway or a month-long beach retreat, Penthouse Paradise by Siesta Key Luxury Rental Properties offers a one-of-a-kind coastal living experience with the space, privacy, and amenities today’s travelers crave. Secure your spot in paradise and make unforgettable memories—reserve your stay today!brbr-brbrThis home is managed by Siesta Key Luxury Rental Properties. 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 Siesta Key Luxury Rental Properties Rental Policies for full details. brbrTwo 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. brbrWe 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 Siesta Key Luxury Rental Properties Rental Policies for full details. 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
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Bath 3

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Sleep 6

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$425.52

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Condo

Village West Unit 101- Close to Beach and Siesta Village

Siesta Key, Florida, United States

Village West Unit 101 by Tropical Sands Accommodations br brWelcome to Village West Unit 101! This ideal Siesta Key escape offers a charming one-bedroom, one-bathroom retreat perfectly situated within walking distance of Siesta Key Beach. This well appointed condo offers a relaxed coastal vibe, making it an excellent romantic getaway or a cozy family retreat. Located just minutes from Siesta Key Village, enjoy easy access to local shops, dining, and vibrant nightlife, all from your private and comfortable oasis! brbrHighlights br• 3-minute walk to Siesta Key Beach br• 1 Bedroom / 1 Bathroom br• Sleeps 4 with 1 King, 1 sleeper sofa br• Screened-in patio   br• Walkable distance to Siesta Key Village shops, restaurants, and nightlife   br• Private parking br• Easy access to local parks, entertainment, and attractions  br• Quiet, family-friendly neighborhood br• Private parking br brEnjoy the privacy and comfort of your screened-in patio, perfect for dining outdoors or relaxing in the fresh ocean breeze. The home’s well designed interior features a cozy living space with modern decor, a fully equipped kitchen for preparing meals, and comfortable furnishings suited for a romantic escape or family getaway. The exterior parking makes coming and going effortless, while neighboring attractions include Siesta Key Village, Crescent Beach, and Siesta Key Beach. br brThe interior of Village West Unit 101 offers a cheerful coastal decor that creates a relaxing ambiance. The living area is perfect for unwinding after a day at the beach, supported by a full kitchen with essential appliances, and a cozy dining space for meals with loved ones. Large windows and screened doors enhance the breezy, island-inspired atmosphere. br brThe bedroom provides a restful space featuring a comfortable king bed with quality linens for a good night's sleep. The bathroom is updated with modern fixtures and a shower, ensuring convenience and style. The living room sleeper sofa provides additional sleeping arrangements for extra guests. Whether you are here for a romantic retreat or a family vacation, the cozy interior guarantees relaxation. brbrRoom Details br• Primary Bedroom: King bed br• Living Room: Sleeper sofa br brGuests enjoy dedicated parking right outside the front door, a screened-in patio for outdoor living, and close proximity to Siesta Key Village. Easy access to local restaurants, shops, and parks makes Village West Unit 101 a fantastic base for exploring Siesta Key. br brBook your stay at Village West Unit 101 today and enjoy a relaxed, island inspired escape just steps from Siesta Key Village and the beautiful beaches. Reserve now and start creating lifelong memories in paradise! br brbr- brThis home is managed by Tropical Sands Accommodations. brbrWith host approval before check-in, this property accepts pets. Weight restrictions apply. An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details.  brbrWe 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. 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.
Bed 2

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Bath 1

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Sleep 4

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$437.31

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Private Vacation Home

Quaint 3-bed 3bath Ocean side retreat with pool and hot tub house in Siesta Key

Siesta Key, Florida, United States

Oceanside Retreat is a recently refreshed three-bedroom, three-bath ground floor vacation rental on Siesta Key, ideal for families and small groups who want a comfortable home base close to the island’s famous beaches, dining, and laid back coastal vibe. After a day on the sand, come home to bright, beachy interiors, plenty of space to spread out, and fun extras that make nights in just as enjoyable as days out exploring Siesta Key.brbrHighlightsbr• 3 Bedrooms / 3 Bathroomsbr• 1 King, 1 Queen, Twin over Full bunk bed with Twin trundlebr• Recently refreshed home on Siesta Keybr• Pool table for indoor funbr• Beach chairs and beach cart providedbr• Washer and dryer in homebr• Pet friendly with host approvalbr• 3 parking spotsbr• Convenient access to Siesta Key beaches, restaurants, and shoppingbrbrThis home is built for easy vacation living. Start your mornings with coffee and sunshine, then load up the beach cart with the provided beach chairs and head out for a classic Siesta Key beach day. When you are ready to wind down, the pool table sets the tone for relaxed evenings and friendly competition. With thoughtful touches throughout and a layout that works well for groups, Oceanside Retreat keeps everyone comfortable while still feeling like a true getaway.brbrThe main living area is open, bright, and inviting, with comfortable seating and a large television that makes it easy to gather for movie nights or a break from the sun. The kitchen is fully equipped with modern appliances, generous counter space, and the essentials you need for everything from quick breakfasts to family style dinners. Nearby dining space gives your group a dedicated spot for meals, games, or planning tomorrow’s Siesta Key adventures.brbrThe primary bedroom is a relaxing retreat with a king bed and a private ensuite bathroom featuring a walk-in shower and a standalone soaking tub, perfect for resetting after a day at the beach. The second bedroom offers a queen bed and its own ensuite bathroom with a walk-in shower, giving another couple or set of guests extra privacy. The third bedroom is a great setup for kids or additional guests, featuring a twin over full bunk bed with a twin trundle. A hallway bathroom with a shower and tub combination is conveniently located for this room and the main living spaces.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk-in shower and standalone tubbr• Second Bedroom: Queen bed, ensuite bathroom with walk-in showerbr• Third Bedroom: Twin over Full bunk bed with Twin trundlebr• Hall Bathroom: Shower and tub combinationbrbrTo keep your stay simple and stress free, Oceanside Retreat includes an in-home washer and dryer so beach towels and vacation outfits stay fresh throughout the week. Beach gear is also provided, so you can spend less time packing and more time enjoying Siesta Key.brbrIf you are looking for a refreshed Siesta Key vacation rental with a comfortable layout, family friendly sleeping options, and beach gear plus at home entertainment, Oceanside Retreat is ready for you. Book your stay with Tropical Sands Accommodations and start counting down to your Siesta Key escape.brbr-brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company.brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.brbrThis home has a security camera located by the entrance.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.brbrWe 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.brbr3 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.
Bed 3

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Bath 3

Bath

Sleep 7

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Exceptional(5)

$235.45

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Private Vacation Home

Private Beach Access w/shared Pool -Casita East

Siesta Key, Florida, United States

Casita East by Siesta Key Luxury Rental Properties brbrWelcome to Casita East! This beach bungalow offers two bedrooms and one bathroom, along with fantastic amenities like private beach access and access to the community pool. If you need more space, Casita West, the neighboring property, is also available for rent. With two bedrooms and one bath, renting both Casita East and Casita West would give you a total of four bedrooms and two baths. So, pack your beach bags and get ready for an amazing vacation on Siesta Key's beautiful beaches! brbrHighlights br• Private Beach Access - One Block Awaybr• Access to Calini Beach Club Resort Community Poolbr• Single Story Residencebr• Shared Patio with Grill and Outdoor Dining Tablebr• Shared Washer & Dryerbr• Catch the FREE Trolley to visit Iconic Siesta Villagebr• Walk to Daquiri Deck, Captain Curt's and other Famous Restaurantsbr• Dog friendly with approval and additional fee brbrUpon entering, you’re welcomed into the cozy living area with two sofas and a tv, perfect for unwinding after a day at the beach. The kitchen has been updated with modern touches and stainless-steel appliances, it’s also equipped with cookware essentials, and has a nautical-theme dining area and table for up to four guests. Outside is a lovely, shared patio with bright landscaping, and an outdoor dining area with a grill. brbrExperience ultimate comfort and relaxation in the primary bedroom, complete with a cozy Queen bed, two nightstands, and a spacious closet to safely store your belongings. The guest bedroom has two twin beds with nautical bedding and a TV. The main bathroom has a large vanity, perfect for storing all your vacation essentials, and a refreshing shower and bath combination. As an added convenience, guests have access to a shared washer and dryer. brbrRoom Details br-Primary Bedroom: Queen bed br-Second Bedroom: Two twin beds brbrThe association's pool and hot tub are available; lounge chairs surround the deck area. The association also has private beach access for guests to enjoy one of the world's best beaches. brbrGet out and venture out to the restaurants, ice cream parlors, boutiques, and the stunning Gulf of Mexico beaches just seconds away from this apartment. Rent a bike, kayak, or paddleboard and explore everything that beautiful Siesta Key offers! brbr-brThis property allows ONE dog with a Max weight of 35lbs with host approval prior to arrival. Please note there will be an additional pet fee associated.brbrThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. brbrThis home is managed by Siesta Key Luxury Rental Properties. We 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. 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.
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Exceptional(4)

$354.4

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Condo

Siesta Beach House #312 – Beach Access and Pool!

Siesta Key, Florida, United States

Siesta Beach House #312 by Tropical Sands Accommodations brbrWelcome to Siesta Beach House #312, a comfortable two-bedroom, two-bathroom condo located just steps from the white sands of Siesta Key Beach. Set within a quiet complex on a private lane, this inviting condo offers gated beach access, making it easy to enjoy stress free beach days. With shared amenities and a relaxed island atmosphere, this is a great option for families or couples looking for budget friendly Siesta Key vacation rentals with classic island charm. brbrHighlights br• 2-minute walk to Siesta Key Beach br• Gated beach access with no streets to cross br• 2 bedrooms / 2 bathrooms br• 1 king bed, 1 queen bed, 1 twin bed br• Shared heated pool br• Shared shuffleboard courts br• Outdoor dining table and sun loungers br• Shared BBQ area br• 1 parking space brbrGuests at Siesta Beach House #312 enjoy a variety of shared amenities designed for easy, laid back beach living. Start your mornings with a short walk to the beach using the private gated access, then cool off in the shared heated pool, perfect for enjoyment. The outdoor common areas feature sun loungers, a shared BBQ area, and an outdoor dining table, ideal for casual meals after a day at the beach. Shuffleboard courts add a touch of old Florida fun, while the peaceful complex offers a relaxed setting for families and couples. brbrInside, the condo offers a bright and welcoming living area with comfortable seating and a TV, creating a cozy place to unwind after a day in the sun. The dining area provides space for shared meals, and the kitchen is well equipped for preparing breakfasts, beach snacks, or simple dinners during your stay. The open layout and coastal decor make the space feel light, comfortable, and easy to enjoy. brbrThe primary bedroom features a comfortable king bed, coastal decor, and a calm atmosphere for restful nights. The second bedroom includes one queen bed and one twin bed, offering flexible sleeping arrangements for families or additional guests. This condo includes two full bathrooms, providing added convenience for everyone in your group. brbrRoom Details br-Primary Bedroom: King bed br-Second Bedroom: One queen bed and one twin bed brbrLocated on Midnight Pass Road, this condo offers easy access to local dining, island activities, and the quieter south end of Siesta Key. Guests enjoy a relaxed setting while remaining close to everything that makes Sarasota vacation rentals for families so popular. brbrIf you are searching for family-friendly condos on Siesta Key with quick beach access, shared amenities, and a relaxed island atmosphere, Siesta Beach House #312 by Tropical Sands Accommodations is an excellent choice. Book your stay today and enjoy an affordable, easygoing beach getaway on the beautiful Siesta Key! br br- br brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind. brbrWe 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. brbrOnly one designated parking space per unit is provided. Visitor parking is no longer permitted. If you plan to bring an additional vehicle, you must notify us in advance so the association can issue a temporary parking pass. Vehicles without proper authorization or a valid parking pass will be ticketed and towed. 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.
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Exceptional(2)

$338.53

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Siesta Beach House #304 – Steps to Beach and Pool!

Siesta Key, Florida, United States

Siesta Beach House #304 by Tropical Sands Accommodations brbrWelcome to Siesta Beach House #304, a beautifully remodeled 2-bedroom, 2-bathroom condo located just steps from the world famous white sands of Siesta Key Beach. Set within a quiet, friendly community on a private lane, this inviting retreat offers gated beach access with no roads to cross, making it easy to enjoy stress free beach days. With modern upgrades, shared amenities, and a relaxed island atmosphere, this condo is ideal for couples or small families seeking budget friendly Siesta Key vacation rentals with classic island charm. One designated parking space is included for your convenience. brbrHighlights br• 2-minute walk to Siesta Key Beach br• Private community lane leading directly to the beach br• 2 bedrooms / 2 bathrooms br• 1 king bed, 1 queen bed, 2 twin beds, 1 queen sleeper sofa br• Shared heated pool br• Shared shuffleboard courts br• Outdoor dining table and sun loungers br• Shared BBQ area br• In-unit washer and dryer br• 1 parking space brbrGuests at Siesta Beach House #304 enjoy access to shared amenities designed for easy, laid back beach living. Take advantage of the shared heated pool, enjoy friendly games on the shuffleboard courts, or gather for casual meals in the shared BBQ area. The private lane provides direct, safe access to the beach, allowing you to move effortlessly between poolside relaxation and Gulf front beach days. brbrStep inside to discover bright, open living spaces with coastal decor and modern finishes throughout. The living room features comfortable seating, a TV, and a queen sleeper sofa, creating a welcoming place to relax after a day in the sun. The updated kitchen is well equipped for preparing meals and beach snacks, while the dining area offers ample space to enjoy meals together. brbrThe primary bedroom features a comfortable king bed along with an additional twin bed, offering flexible sleeping options and a calm setting for restful nights. The second bedroom includes one queen bed and one twin bed, making it ideal for families or additional guests. With two full bathrooms, the condo provides added comfort and convenience for everyone in your group. brbrRoom Details br-Primary Bedroom: King bed and one twin bed br-Second Bedroom: One queen bed and one twin bed br-Living Room: Queen sleeper sofa brbrAn in-unit washer and dryer adds convenience for longer stays, while the location places you close to island dining, shopping, and local attractions. Guests enjoy a quieter south end setting while still being just minutes from everything that makes Sarasota vacation rentals for families so popular. brbrIf you are looking for a family friendly Siesta Key condo with quick beach access, modern updates, and a relaxed island setting, Siesta Beach House #304 by Tropical Sands Accommodations is an excellent choice. Book your stay today and enjoy an affordable, unforgettable Siesta Key getaway! br br- brbrThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind. brbrWe 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. brbrOnly one designated parking space per unit is provided. Visitor parking is no longer permitted. If you plan to bring an additional vehicle, you must notify us in advance so the association can issue a temporary parking pass. Vehicles without proper authorization or a valid parking pass will be ticketed and towed. 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.
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$315.0

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Modern Siesta Key Condo – Just Steps from the Beach & Community Amenities!

Siesta Key, Florida, United States

Midnight Cove II 613F by Tropical Sands Accommodations brCondo in Sarasota FL 34242 brbrEscape to paradise at Midnight Cove II 613F, a modern 2-bedroom, 1.5-bathroom Siesta Key condo. Enjoy easy access to the world-famous Siesta Key Beach, just a short stroll away, and hop on the Siesta Key Breeze Trolley for a quick ride to the vibrant Siesta Key Village, brimming with charming shops, exceptional dining, and exciting entertainment. brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Picnic/Grilling Areabr• Bike racks throughout propertybr• Cornholebr• Private Washer and Dryer br• Beach Chairs Provided brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Siesta Key Beach and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrStep inside to a bright and airy living space, featuring comfortable seating and a fully equipped kitchen with a refrigerator, stove, dishwasher, and microwave. Share memorable meals in the inviting dining area. The master bedroom boasts a king-size bed, and the second bedroom offers a queen-size bed, comfortably accommodating up to four guests. A full bathroom with shower/tub combination and a convenient half bath enhance your comfort. brbrBook your unforgettable Siesta Key getaway at Midnight Cove II 613F today and create lasting memories in this coastal paradise!
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Exceptional(19)

$375.16

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Your New Happy Place! Modern Jamaica Royale Villa: Private Beach Access, 3 Pools, VIP Perks Daily!

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWELCOME TO JAMAICA ROYALE END-UNIT VILLA brbr brbrFreshly renovated from top to bottom, this 1-bedroom end-unit villa offers modern comfort and unbeatable access to Jamaica Royale’s private beach. With new flooring, furniture, appliances, and stylish finishes, this villa provides a relaxing retreat just steps from the sand. The bonus An additional half bath and the privacy of a quiet end location near BBQ grills and shuffleboard. brbr brbrPROPERTY HIGHLIGHTS brbrDirect private walkway to Jamaica Royale’s beach brbrEnd-unit privacy with quick access to grills and shuffleboard brbrTwo bathrooms: one full bath plus a convenient half bath brbrThree heated pools, including one near the Gulf brbrPrivate patio with outdoor dining table brbrNew stainless steel kitchen with stone counters and full cookware brbrUncovered parking conveniently located at the entrance brbr brbrSLEEPING ARRANGEMENTS brbrBedroom: Two queen beds, brand new as of November 2025. brbrLiving room: Queen sleeper sofa brbrSleeps up to 6 guests brbr brbrINSIDE THE VILLA brbrOpen living and dining area with new furnishings and Smart TV brbrFully equipped kitchen with new appliances and stone countertops brbrUpdated full bathroom with modern fixtures, plus a powder room brbrIn-unit washer and dryer brbrKeyless entry for easy check-in brbrTwo Smart TVs, cable included, and fast Wi-Fi throughout brbr brbrRESORT AMENITIES brbrThree heated pools brbrTennis courts and shuffleboard brbrOutdoor BBQ grilling areas brbrBeautifully landscaped grounds with private beach access brbr brbrLOCATION brbrJust steps from pools, short 5 minute walk to private beach access brbr1.5 miles to Siesta Key Village for shopping, dining, and live music brbrPark once and use local ride services to explore the island hassle-free brbr brbrGOOD TO KNOW brbrSingle-story garden villa in a quiet end-unit setting brbrCourtyard views from the living room and lanai brbrPhotos reflect the current renovation brbr brbrBOOK YOUR STAY AT JAMAICA ROYALE VILLA TODAY brbr brbrEnjoy the perfect mix of modern comfort, end-unit privacy, two bathrooms, and a short walk to the sand on world-famous Siesta Key.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.
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