Holiday Homes in Siesta Key

The 2-bedroom Siesta Bayside Bliss Villa Siesta Key accommodates up to 4 guests and offers proximity to Edson Keith Estate Park, located just 9 minutes' walk away. This holiday home features… More

Welcoming guests with a sauna, the 2-bedroom Spacious 2Br Siesta Key Condo With Private Beach Access villa is located around a 5-minute walk from the Jamaica Royale and can host up to 4 guests. This… More

Situated only a 9-minute walk from the Jamaica Royale, Coastal Comfort Steps From Crescent Beach Paradise - Aloha Kai #63 - Roelens Siesta Key villa is ideal for up to 4 guests. This property… More

Offering a sauna, the 2-bedroom Extraordinary Bay Views - Siesta Key Villa is situated only a 6-minute walk from the Siesta Key Village and can accommodate 4 people. The holiday home features… More

Featuring horse riding tours to make your visit more entertaining, Casita Sun Star - 1135 Villa Siesta Key is 25 minutes' walk from the Jamaica Royale. Guests can enjoy snorkelling, horse riding, and… More

The 3-bedroom Bali Hai House - 5041 Siesta Key villa hosts up to 8 guests and is nestled 3.1 km from natural sites such as the shaped Crescent Beach. Located about a 10-minute drive from the Siesta… More

Bayfront 2Br Siesta Key Condo With Beach Access - Gbb 1382 villa is located merely a 5-minute walk from the Jamaica Royale and offers a sauna, ensuring guests a relaxing stay. The 2-bedroom holiday… More

Luxe Siesta Key Home Pool Hot Tub Near Beach, located merely 9 minutes' walk from the Siesta Key Craft Festival, invites guests to relax in a Jacuzzi. This property can host up to 8 guests and offers… More

Casa Del Mar - Pet Friendly House On Siesta Key W/ Outdoor Patio & Private Screened-In Heated Pool! is nestled just a 5-minute walk from the Grand Canal and can accommodate up to 8 guests. More

Cinco Siesta By Beachside Management Siesta Key villa, located nearly a 5-minute walk from the Sarasota Beach, invites guests to relax in a Jacuzzi. The accommodation can host up to 14 guests and… More

The 1-bedroom Bay Oaks C Ground Floor Villa Siesta Key hosts up to 6 guests and provides proximity to the shaped Crescent Beach, situated only 350 metres away. The welcoming holiday home boasts a… More

The 4-bedroom Off The Hook By Beachside Management Siesta Key villa accommodates up to 8 guests and offers a prime location within 6 km of shopping venues such as the upscale Saint Armands Circle… More

Offering a year-round outdoor pool, the 3-bedroom Lakefront Siesta Key Condo With Beach Access villa is located only 5 minutes' walk from the Jamaica Royale and is ideal for up to 6 guests. Featuring… More

During the stay at Crescent Royale Condominiums 403 Siesta Key villa, guests can indulge in snorkelling, pool, and fishing or visit the Jamaica Royale, located a 13-minute walk away. More

The 10-room Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1 Mile And Crescent Beach 2 Miles, 1Bdr villa is located 4.8 km from the Siesta Key Beach and provides canoeing and fishing for… More

Between The Waves - Siesta Key Luxury Home is nestled just 5 minutes' walk from the Siesta Key Beach Access 2 and can accommodate up to 17 guests. More

Offering a Jacuzzi for guests to unwind, the 1-bedroom Top Gulf Siesta Key villa is located around 5 minutes' walk from the Siesta Key Beach Access 7. This accommodation features opportunities for… More

Welcoming guests with a sauna, the 3-bedroom Serene Bay Front Condo On Siesta Key - 2 Heated Pools, Pickleball And Tennis, Private Beach Access villa is located just 5 minutes' walk from the Jamaica… More

Offering an outdoor swimming pool, the 2-bedroom Crescent Royale Condominiums 306 Siesta Key villa is located only 500 m from the Siesta Key Beach and is ideal for up to 6 guests. This accommodation… More

The welcoming Harbor Towers 3Rd Fl Views Of The Bay Villa Siesta Key hosts up to 5 guests and provides proximity to the Jamaica Royale, situated merely 6 minutes' walk away. More

Offering a foot bath for a relaxing experience, Luxury Penthouse, Ocean Views, Rare Rooftop Sundeck, Private Access To Beach Siesta Key villa is located 18 minutes' walk from the Siesta Key Drum… More

Located around a 5-minute walk from Green Turtle Shell & Gift City, Casita West Villa Siesta Key offers quick access to various city attractions in the vicinity. The property features opportunities… More

Located around a 5-minute walk from the Jamaica Royale, the 2-bedroom Relaxing Siesta Key Condo With Private Beach Access villa offers a year-round outdoor swimming pool for guests to relax by. More

The 3-bedroom Seahorse Cabana - 1106 Siesta Key accommodates up to 8 guests and offers proximity to the Siesta Key Marina, located merely a 7-minute walk away. This holiday home features… More

During the stay at Island Sun Villa Siesta Key, guests can indulge in fishing or visit the Siesta Key Village, located 16 minutes' walk away. More

Located only 0.7 km from the Siesta Key Marina, Midnight Cove II 820F Villa Siesta Key offers opportunities for lawn tennis and fishing in the area. More

Sea Foam - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach! villa hosts up to 4 guests and provides proximity to the Siesta Key Beach Access 2, situated only 5 minutes' walk… More

Overlooking the sea, Ocean Overlook Siesta Key villa enjoys a convenient setting a 5-minute stroll from the Sarasota Beach. Located 4.6 km from Sarasota Square, this holiday home provides Wi-Fi and a… More

Coastal Condo, Water Views, Fishing Dock & 0.6 Miles To Siesta Beach Siesta Key villa is located 8 minutes' walk from the Crescent Arms and offers guests to enjoy windsurfing, snorkelling, and mini… More

The 2-bedroom Keylime Retreat Villa Siesta Key accommodates up to 6 guests and offers proximity to Siesta Key Beach Access 7, located merely 5 minutes' walk away. This property features opportunities… More

Offering a Jacuzzi, New Listing - Dates Available Now! Beach & Village, Pool, Dock, Game Room! Siesta Key villa is located 13 minutes' walk from the Siesta Beach Pavillion. Guests can enjoy… More

Offering an outdoor swimming pool, the 2-bedroom Crescent Royale Condominiums 4A Siesta Key villa is located just 6 minutes' walk from the Siesta Key Beach and is ideal for up to 6 guests. This… More

Situated about a 5-minute walk from the Siesta Key Beach Access 7, Ocean-Views, Pool, Covered Patio, 150 Steps To Beach! Siesta Key villa is ideal for up to 10 guests. The holiday home features… More

The 3-bedroom Island Home In Paradise Siesta Key is nestled a mere 450 metres from the Seaside Vacation Villas and provides a Jacuzzi. More

Situated approximately a 5-minute walk from the Jamaica Royale, 3-bedroom Bayfront Condo In The Heart Of Siesta Key villa is ideal for up to 6 guests. Featuring a sauna, the property is 4.4 km from… More

The 4-bedroom Casa Stolida - 1030L Villa Siesta Key entices guests to enjoy snorkelling, horse riding, and ping-pong and offers proximity to the Siesta Key Marina, located only 500 metres away. The… More

Situated just 5 minutes on foot from the Siesta Key Beach Access 2, Sea Coast - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach! villa ensures a great leisure experience by… More

Situated just 5 minutes' stroll from Green Turtle Shell & Gift City, Sunrise Villa Siesta Key offers opportunities for fishing in the area. Featuring a hot tub, the accommodation is nestled 2.6 km… More

Excelsior 401 Villa Siesta Key, located just 5 minutes' walk from Siesta Harbour Condominium, can host up to 6 guests. More

The 3-bedroom Sea Esta Villa Siesta Key is located around 25 minutes on foot from the Jamaica Royale and allows guests to enjoy canoeing. The Siesta Key holiday home can host up to 10 guests and… More

Overlooking the sea, Crescent Royale Condominiums108 Siesta Key villa enjoys a prime setting a 6-minute walk from the Public Beach Access 10. Located 3.9 km from the Nora Patterson Bay Island Park… More

Featuring an outdoor swimming pool as well as views of the sea, Crescent Royale Condominiums 3E Siesta Key villa offers a prime location merely a 5-minute walk from the Siesta Beach Pavillion. More

Staying at the 3-bedroom Beautiful Siesta Key Condo - Two Heated Pools, Tennis, Pickleball, Private Beach Access villa, guests can visit the Siesta Key Beach, which is nearly a 20-minute walk away. More

Located about 5 minutes on foot from the Jamaica Royale, the 2-bedroom Watch Dolphins From Your Lanai In This Bayfront Siesta Key Condo villa can accommodate up to 4 guests, providing them with a… More

Jamaica Royale Beach Villa Siesta Key enjoys a beachfront location 0.6 km from the Jamaica Royale, and invites guests to spend time on a sun deck. Located a 25-minute stroll from the Crescent Arms… More

Casa Mar #9-Studio Siesta Key is nestled a 9-minute walk from the Crescent Arms and can accommodate up to 3 guests. More

The 4-bedroom Island Escape - 638 Villa Siesta Key accommodates up to 12 guests and offers proximity to the Siesta Key Beach Access 7, located merely 350 metres away. This Siesta Key holiday home… More

Located 25 minutes' walk from the Crescent Arms, Crescent Royale Condominiums 4E Siesta Key villa offers a games room for guests' leisure. The 2-bedroom holiday home features opportunities for… More

Situated approximately a 5-minute stroll from the Crescent Arms, the 1-bedroom Crystal Sands & Seahorses Beach Villa Siesta Key is suitable for 6 guests and provides a heated swimming pool to relax… More

During the stay at Luxury Condo, Ocean Views, Rare Rooftop Sundeck Siesta Key villa, guests can indulge in a foot bath or visit the Shell Beach, located 3 km away. The 3-bedroom holiday home hosts up… More