$104/night

Curtiss Ave Condo

$104/night

Curtiss Ave Condo

Curtiss Cove is a bright and airy 2-bedroom, 2-bath condo in the peaceful Crossings community of Sarasota. Featuring coastal minimalist design, a screened lanai, and an open layout with in-unit laundry, this home provides both comfort and convenience. Guests enjoy assigned parking, a community pool just a short walk away, and quiet residential surroundings. Siesta Key Beach is a quick 10-minute drive, making this the perfect retreat for beach lovers and those seeking a relaxing getaway.

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$243/night

Harbour Town #211

$243/night

Harbour Town #211

Harbor Breeze Retreat offers a classic coastal vibe in the heart of Harbour Towne Yacht Club. Relax on the screened lanai overlooking boats, take a short 5-minute walk to the community pool, or stroll 10 minutes to the nearby beach and tennis courts. With two bedrooms, a loft with workspace, in-unit laundry, and assigned parking, this peaceful, gated community unit makes for an ideal Florida getaway. Trolley service is conveniently just outside the gates. Towels provided for your convenience.

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$104/night

Lil Oasis

$104/night

Lil Oasis

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$285/night

Peppertree 1126

$285/night

Peppertree 1126

Peppertree Breeze Villa offers a peaceful coastal retreat on Siesta Key with 2 bedrooms, 2 baths, and a screened lanai perfect for relaxing. Enjoy resort amenities like a pool, private beach access, tennis courts, and a fitness center. The master bedroom includes a workspace, ideal for those blending work and leisure. With in-unit laundry, assigned parking, and a prime location near the village and beaches, this villa is perfect for extended stays. A 15-day HOA application is required, and a one-month minimum stay applies year-round, except when checking out on the first or last day of the month.

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$259/night

Peppertree 1136

$259/night

Peppertree 1136

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$349/night

Provincial Gardens N3

$349/night

Provincial Gardens N3

Casa Mareo offers a classic coastal retreat in Siesta Key’s prestigious Provincial Gardens. This remodeled 2-bedroom, 2-bath home features timeless Pottery Barn-inspired décor that looks like a magazine spread. Just a short 5-minute walk to deeded beach access and pool, with bay access for kayaking and boating. Enjoy a shaded courtyard with outdoor dining and a dedicated workspace. The community is quiet and welcoming, with assigned parking and essential beach gear provided.

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$311/night

Provincial Gardens N4

$311/night

Provincial Gardens N4

The Terra Grove Villa is a serene, earthy retreat in Siesta Key’s Provincial Gardens. Featuring two queen bedrooms, two bathrooms, a cozy sunroom, and a den workspace, it’s ideal for relaxing or working remotely. Enjoy a gated shaded patio and easy access to deeded beach and bay areas just five minutes away. The Aloha Kai pool and shuffleboard court are across the street, and the trolley stop is a one-minute walk for Village dining and entertainment. Beach chairs and towels included. Part of the SK Collection by Siesta Stays.

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$207/night

Provincial Gardens N13

$207/night

Provincial Gardens N13

Sunrise Porch Lookout is an airy coastal classic retreat at Provincial Gardens with a screened lanai overlooking the water. Enjoy deeded Siesta Key Beach access, heated pool, and kayak launch just steps away. Inside, the 1-bed/1-bath layout features a king bedroom, full kitchen, washer/dryer, and a bright living area that opens to a breezy lanai. Five-minute walk to beach and pool, one-minute to trolley stop for easy trips to Siesta Village. Extras include beach towels and chairs, parking pass, and quiet streets. Part of the SK Collection by Siesta Stays.

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$311/night

Provincial Gardens S4

$311/night

Provincial Gardens S4

The Beachwood Hideout offers coastal chic comfort in a beautifully updated 2-bedroom, 2-bath condo at Siesta Key’s Provincial Gardens. Enjoy a modern kitchen, screened patio for outdoor dining, deeded beach access, and a heated pool just across the street at Aloha Kai. Beach chairs and towels provided. Assigned parking and in-unit washer/dryer add convenience. The trolley stop is a 1-minute walk, making exploring the Village easy. HOA quiet hours and parking pass required. Part of the SK Collection by Siesta Stays.

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$309/night

Provincial Gardens S5

$309/night

Provincial Gardens S5

Enjoy a bright tropical getaway at The Citrus Hideout in Provincial Gardens. This 2-bedroom, 2-bath condo features vibrant lime, orange, and red accents, a screened porch for outdoor dining, and a gated patio to relax. Guests have deeded beach access just a five-minute walk away, with chairs and towels provided, plus pool access across the street at Aloha Kai. Assigned parking and a trolley stop two minutes away make exploring Siesta Key easy and convenient. Part of the SK Collection by Siesta Stays.

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$243/night

SaraSea 7

$243/night

SaraSea 7

Seaside Haven at Sarasea is a bright and inviting 2-bedroom, 2-bath condo just a 2-minute walk from Siesta Key Beach. Featuring a clean, updated kitchen, private lanai, and a desk workspace, this simple and comfortable home is ideal for both relaxation and remote work. Guests enjoy assigned parking, shared laundry, and close proximity to shops, restaurants, and the trolley stop. Part of the SK Collection by Siesta Stays.

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$186/night

Sea Winds 118

$186/night

Sea Winds 118

Sea Breeze is a warm, traditional 1-bedroom condo nestled in the peaceful Sea Winds complex of Siesta Key. Designed with couples in mind, this charming retreat features a private patio, cozy interiors with inviting warm tones, and full access to a community pool and laundry facilities. Just a short 5 to 10-minute walk brings you to the pristine sands of Siesta Key Beach, while a nearby trolley stop offers easy access to the Village’s shops, restaurants, and entertainment. Assigned parking completes the convenience. Sea Breeze is the perfect blend of comfort and coastal charm for your next getaway, part of the SK Collection by Siesta Stays.

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