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2026-11-03
2026-11-04
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Siesta Key Vacation Rentals

Beachpoint Cottages

125 Beach Road, Siesta Key, United States Show map

The 8-room Beachpoint Cottages Siesta Key apartment lies in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida and offers swift access to Siesta Key Beach… More

From US$ 299 Book Now

The Inn At Turtle Beach (Adults Only)

9004 Midnight Pass Road, Siesta Key, United States Show map

The 10-room The Inn At Turtle Beach Siesta Key lies in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida and offers swift access to Turtle Beach, which… More

From US$ 210 Book Now

Our House At The Beach 502E By Beachside Management

1001 Beach Road, Siesta Key, United States Show map

Situated nearly a 5-minute walk from Siesta Beach Pavillion, the spacious 2-bedroom Our House At The Beach 502E By Beachside Management Siesta Key offers guests easy access to various tourist… More

From US$ 550 Book Now

Ten35 Seaside Rentals

1035 Seaside Drive, Siesta Key, United States Show map

The spacious Ten35 Seaside Rentals Siesta Key apartment is located in Siesta Key, a 25-minute walk from Edson Keith Estate Park, and pampers guests with a Jacuzzi. This apartment features Wi-Fi in… More

From US$ 347 Book Now

Island Villa | Cozy Beach Retreat | Private Dock

368 Canal Road Island, Siesta Key, United States Show map

Situated 14 minutes' walk from Siesta Key Drum Circle, the 74 m² Island Villa | Cozy Beach Retreat | Private Dock Siesta Key can host up to 4 guests in Siesta Key. More

From US$ 314 Book Now

Gulf Holiday By Beachside Management

73 Avendia Messina, Siesta Key, United States Show map

Gulf Holiday By Beachside Management Siesta Key apartment is nestled in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida, an 8-minute walk from the… More

From US$ 171 Book Now

Beachfront Getaway In Siesta Key

1129 Seaside Drive 7, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the 1-bedroom Beachfront Getaway In Siesta Key apartment, which is approximately 25 minutes' walk from Escape Countdown and just 0.6 km from Christopher… More

From US$ 224 Book Now

Siesta Key Condo - On The Water !

5955 Midnight Pass Road 14E, Siesta Key, United States Show map

56 m² Siesta Key Condo - On The Water ! is a great place to stay in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida, a 16-minute walk from Siesta Beach… More

From US$ 310 Book Now

Living The Dream By Beachside Management

139 Beach Road, Siesta Key, United States Show map

The 74 m² Living The Dream By Beachside Management Siesta Key apartment boasts a prime setting and in only a 7-minute walk from Siesta Key Beach Access 2. The 3-room apartment features Wi-Fi, along… More

From US$ 234 Book Now

Siesta Key Escape Ground Floor Steps To Heated Pool And Free Trolley

6157 Midnight Pass Road E31, Siesta Key, United States Show map

The 2-bedroom Siesta Key Escape Ground Floor Steps To Heated Pool And Free Trolley Apartment is located 3.9 km from Gulf Gate Public Library and approximately a 15-minute walk from the shaped… More

From US$ 242 Book Now

Siesta Cooler: Only Minutes Walk To Siesta Beach!

5424 Ocean Boulevard, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 1-bedroom Siesta Cooler: Only Minutes Walk To Siesta Beach! Siesta Key apartment, which is 3.5 km from Crescent Arms and around 10 minutes'… More

From US$ 286 Book Now

Siesta Cool: Only Minutes Walk To Siesta Beach!

5242 Ocean Boulevard, Siesta Key, United States Show map

The spacious 70 m² Siesta Cool: Only Minutes Walk To Siesta Beach! Siesta Key apartment is merely an 8-minute stroll from Siesta Key Beach Access 2 and can accommodate up to 3 guests. The 1-bedroom… More

From US$ 312 Book Now

Jamaica Royale 101

5830 Midnight Pass Rd, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at Jamaica Royale 101 Apartment Siesta Key, which is 2.4 km from Siesta Key Beach Access 7 and about a 5-minute drive from Siesta Key Beach. More

From US$ 246 Book Now

Beachside Studio Located Across From Main Beach And Half Mile To Village

665 Beach Road, Siesta Key, United States Show map

Featuring a prime location approximately 5 minutes' walk from Public Beach Access 10, the 1-bedroom Beachside Studio Located Across From Main Beach And Half Mile To Village Siesta Key accommodates up… More

From US$ 177 Book Now

Studio Retreat Across The Street From Beautiful Siesta Key Beach

665 Beach Road, Siesta Key, United States Show map

33 m² Studio Retreat Across The Street From Beautiful Siesta Key Beach is nestled in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida, 8 minutes' walk… More

From US$ 169 Book Now

Jamaica Royale Beachfront Tower By Beachside Management

5830 Midnight Pass Road, Siesta Key, United States Show map

Located approximately 20 minutes' walk from Siesta Beach, the 2-room Jamaica Royale Beachfront Tower By Beachside Management Siesta Key apartment offers modern comforts like Wi-Fi and essentials like… More

From US$ 420 Book Now

Siesta Key Beach - 2 Bedroom - 3 Beds - 3 Bathroom Duplex With Heated Swimming Pool

6157 Midnight Pass Road, Siesta Key, United States Show map

The 111 m² Siesta Key Beach - 2 Bedroom - 3 Beds - 3 Bathroom Duplex With Heated Swimming Pool, located in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota… More

From US$ 428 Book Now

Midnight Cove #532, Bayside In Siesta Key, Fl

6304 Midnight Cove Road, Siesta Key, United States Show map

Featuring views of the garden, the 80 m² Midnight Cove #532, Bayside In Siesta Key, Fl Apartment is situated in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota,… More

From US$ 372 Book Now

Parrot Beach Cottages Suite #2

60 Avenida Vennecia #2, Siesta Key, United States Show map

The 23 m² Parrot Beach Cottages Suite #2 Siesta Key is located 400 metres from Siesta Key Craft Festival Museum and about a 25-minute walk from Siesta Key Drum Circle. Offering access to a swimming… More

From US$ 236 Book Now

Gertrude'S Siesta | 1 Min Walk To Beach Path | 4 Min To Dining, Music & Sunsets!

6905 Point Of Rocks Road, Unit #B, Siesta Key, Florida 34242, United States, Siesta Key, United States Show map

The spacious 1-bedroom Gertrude'S Siesta | 1 Min Walk To Beach Path | 4 Min To Dining, Music & Sunsets! Siesta Key apartment boasts a prime location approximately 500 metres from Siesta Key Marina. More

From US$ 1193 Book Now

Newly Remodeled 8-Steps To Sand Path Of Beach! Unit A

6905 Point Of Rocks Road, Unit #A N/A, Siesta Key, Florida 34242, United States, Siesta Key, United States Show map

The spacious Newly Remodeled 8-Steps To Sand Path Of Beach! Unit A Siesta Key apartment is within a 500-metre distance of Siesta Key Marina and can accommodate up to 8 guests. Wi-Fi and parking are… More

From US$ 676 Book Now

Our House At The Beach 501W By Beachside Management

1001 Beach Road, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 112 m² Our House At The Beach 501W By Beachside Management Siesta Key, which is 3.9 km from Nora Patterson Bay Island Park and within 5… More

From US$ 330 Book Now

Newly Remodeled 8-Steps To Sand Path Of Beach! Unit D

6905 Point Of Rocks Road, Unit #D, Siesta Key, Florida 34242, United States, Siesta Key, United States Show map

Located only a 7-minute stroll from Siesta Key Marina, the spacious 84 m² Newly Remodeled 8-Steps To Sand Path Of Beach! Unit D Siesta Key apartment accommodates up to 8 guests. Enjoying a prime… More

From US$ 520 Book Now

Sea Club II By Beachside Management

5955 Midnight Pass Road, Siesta Key, United States Show map

Sea Club II By Beachside Management Siesta Key apartment is located 3.9 km from the friendly Edson Keith Estate Park and 16 minutes' walk from Siesta Beach Pavillion. Wi-Fi and a car park are also… More

From US$ 171 Book Now

A Somewhere Is Here By Beachside Management

640 Calle Del Otono, Siesta Key, United States Show map

Featuring a year-round outdoor swimming pool, A Somewhere Is Here By Beachside Management Siesta Key apartment is a 5-minute walk from Public Beach Access 10. Wi-Fi and parking are among the… More

From US$ 559 Book Now

Just Beachy By Beachside Management

450 Beach Road, Siesta Key, United States Show map

Situated approximately 5 minutes on foot from Siesta Key Beach Access 7, the 3-room Just Beachy By Beachside Management Siesta Key apartment looks out onto the sea. The spacious apartment enjoys a… More

From US$ 1194 Book Now

Siesta Breakers #603, Gulfside In Siesta Key, Fl

6480 Midnight Pass Road Unit #603, Siesta Key, United States Show map

The spacious 2-bedroom Siesta Breakers #603, Gulfside In Siesta Key, Fl Apartment offers setting in a beach area of Siesta Key, just 6 minutes' walk from Siesta Key Marina. Located in Siesta Key… More

From US$ 299 Book Now

Siesta Key Inn

1125 Point Of Rocks Road, Siesta Key, United States Show map

Situated nearly a 5-minute walk from Crescent Beach, the 3-room Siesta Key Inn offers views of the pool. This apartment provides guests with amenities such as an iron and ironing board, dryers to… More

From US$ 324 Book Now

Palm Bay Club By Beachside Management

5960 Midnight Pass Road, Siesta Key, United States Show map

The spacious Palm Bay Club By Beachside Management Siesta Key apartment is located in Siesta Key, around 25 minutes' walk from Siesta Key Beach Access 7, and offers a swimming pool with a hot tub. More

From US$ 462 Book Now

Midnight Cove #714, Bayside In Siesta Key, Fl

6350 Midnight Cove Road Unit #714, Siesta Key, United States Show map

Midnight Cove #714, Bayside In Siesta Key, Fl Apartment is located in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida a 5-minute walk from Crescent… More

From US$ 155 Book Now

Beachfront Condo Complex, Heated Pool, Gulfview!

6312 Midnight Pass Road 205, Siesta Key, United States Show map

Located approximately 5 minutes' walk from Crescent Arms and Siesta Harbour Condominium Apt Harbor, the 2-bedroom Beachfront Condo Complex, Heated Pool, Gulfview! Siesta Key features views of the… More

From US$ 309 Book Now

Oceanview Penthouse, In Village, 30-Steps To Best Beach, Tiki-Bar, Free Bikes And Paddle-Boards!

603 Beach Rd #Penthouse, Siesta Key, Florida, 34242, *2Nd Floor, Siesta Key, United States Show map

Situated around a 5-minute walk from Siesta Key Beach Access 7, the 111 m² Oceanview Penthouse, In Village, 30-Steps To Best Beach, Tiki-Bar, Free Bikes And Paddle-Boards! Siesta Key apartment offers… More

From US$ 1252 Book Now

Beachside Of The Village By Beachside Management

100 Columbus Boulevard, Siesta Key, United States Show map

Located merely 11 minutes' stroll from Siesta Key Beach Access 2, the spacious 182 m² Beachside Of The Village By Beachside Management Siesta Key apartment accommodates up to 4 guests. Enjoying a… More

From US$ 904 Book Now

Coastal Surfside By Beachside Management

298 Beach Road, Siesta Key, United States Show map

The spacious Coastal Surfside By Beachside Management Siesta Key apartment is located a mere 1.4 km from Siesta Key Beach and a 17-minute walk from Siesta Key Drum Circle. Wi-Fi and a car park are… More

From US$ 423 Book Now

Gertrude'S Siesta |1 Min Walk To Beach Path | Near Dining, Music, Hammocks & Sunsets!

6905 Point Of Rocks Road, Unit #C N/A, Siesta Key, Florida 34242, United States, Siesta Key, United States Show map

Located a 7-minute walk from Siesta Key Marina, Gertrude'S Siesta |1 Min Walk To Beach Path | Near Dining, Music, Hammocks & Sunsets! Siesta Key apartment accommodates up to 3 guests. Wi-Fi and… More

From US$ 480 Book Now

Stay Siesta Dunes By Beachside Management

6200 Midnight Pass Road, Siesta Key, United States Show map

Stay Siesta Dunes By Beachside Management Siesta Key apartment is located in Siesta Key, which is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida, around 300 metres from… More

From US$ 459 Book Now

Luxury Waterfront Views - Heated Pool - 1400Sf Duplex - Minutes To The Beach

6157 Midnight Pass Road B32, Siesta Key, United States Show map

Located nearly 5 minutes' walk from the shaped Crescent Beach and Siesta Harbour Condominium Apt Harbor, the spacious 2-bedroom Luxury Waterfront Views - Heated Pool - 1400Sf Duplex - Minutes To The… More

From US$ 417 Book Now

Direct Beachfront Delight By Beachside Management

524 Beach Road C, Siesta Key, United States Show map

Siesta Key Beach Access 2 is merely 1.2 km from Direct Beachfront Delight By Beachside Management Siesta Key apartment, while Public Beach Access 10 is situated nearby. More

From US$ 617 Book Now

Cozy Family Condo - Newly Renovated On Siesta Key!

6157 Midnight Pass Road A52, Siesta Key, United States Show map

The 2-bedroom Cozy Family Condo - Newly Renovated On Siesta Key! enjoys a convenient location just a 9-minute walk from Crescent Arms. Wi-Fi and a car park are also available at this apartment. More

Book Now

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

5223 Calle Menorca Starfish, Siesta Key, United States Show map

Situated around a 20-minute walk from Siesta Key Beach, the 33 m² Cozy Siesta Key Dream Inn Rental 1/2 Mi To Beach can host up to 3 guests in Siesta Key. At this 1-bedroom apartment, Wi-Fi and… More

From US$ 279 Book Now

You Can'T Get Closer To The Beach Than This Beachy 3 Bedroom Condo

564 Beach Road, Siesta Key, United States Show map

The 3-bedroom You Can'T Get Closer To The Beach Than This Beachy 3 Bedroom Condo Siesta Key offers easy access to such tourist sites as Public Beach Access 10, located around 5 minutes' walk away. Wi… More

From US$ 662 Book Now

Hawks Sea Nest

1055 Beach Road, Siesta Key, United States Show map

The spacious 112 m² Hawks Sea Nest Apartment Siesta Key is a mere 6 minutes on foot from Siesta Key Beach and can accommodate up to 4 guests. The 2-bedroom apartment is 4.2 km from Sarasota Square, 3… More

From US$ 371 Book Now

Parrot Beach Cottages Suite #4

60 Avenida Vennecia #4, Siesta Key, United States Show map

The 32 m² Parrot Beach Cottages Suite #4 Siesta Key is located 4.2 km from Public beach and only a 7-minute walk from the co-op Gallery on Siesta Key. This 1-bedroom apartment can hold up to 4 guests. More

From US$ 189 Book Now

Gertrude'S Siesta | 1 Min Walk To Beach Path | Free Bikes, Boards & Trolley!

603 Beach Road, Siesta Key, Florida 34242, United States, Siesta Key, United States Show map

Situated just 1.5 km from Siesta Key Village, the 1-bedroom Gertrude'S Siesta | 1 Min Walk To Beach Path | Free Bikes, Boards & Trolley! Siesta Key apartment can host up to 4 guests in Siesta Key. Wi… More

From US$ 385 Book Now

Siesta Key Beach Condo

5924 Midnight Pass Road, Siesta Key, United States Show map

The spacious 139 m² Siesta Key Beach Condo is located in Siesta Key, around 5 minutes by car from Siesta Key Marina, and offers guests an outdoor swimming pool and a fitness club. Providing a… More

Book Now

Stunning Ocean-View Penthouse! Spacious, New, In Village, 20 Steps To Best Beach!

711 Beach Rd. #408, Siesta Key, United States Show map

A prime location of the 84 m² Stunning Ocean-View Penthouse! Spacious, New, In Village, 20 Steps To Best Beach! Siesta Key apartment provides easy access to Jamaica Royale about 20 minutes' walk away… More

Book Now

Jamaica Royale #40 - 3 Heated Pools On The Beach!

5830 Midnight Pass Road 40, Siesta Key, United States Show map

The 71 m² Jamaica Royale #40 - 3 Heated Pools On The Beach! Siesta Key apartment enjoys a beachfront location around a 5-minute walk from Jamaica Royale. This 1-bedroom apartment offers modern… More

From US$ 387 Book Now

Coastal Surfside Swank By Beachside Management

302 Beach Road, Siesta Key, United States Show map

The spacious 169 m² Coastal Surfside Swank By Beachside Management Siesta Key apartment offers a prime location around a 5-minute stroll from Sarasota Beach. The 3-bedroom apartment features Wi-Fi… More

From US$ 1027 Book Now

Beach Walk

650 Calle Del Otono # C, Siesta Key, United States Show map

Beach Walk Siesta Key apartment offers proximity to such tourist attractions as Siesta Key Beach Access 7, situated around 5 minutes' walk away. More

From US$ 397 Book Now

Walk To The Beach And Village - Gulf Villa

368 Canal Road Gulf, Siesta Key, United States Show map

Situated only a 14-minute walk from Siesta Key Beach, the 102 m² Walk To The Beach And Village - Gulf Villa Siesta Key can host up to 6 guests in Siesta Key. More

From US$ 477 Book Now