
Siesta Beach, Sarasota
10/14 – 10/21
$379/nighttotal: $2653 (7 )
Tropical Sarasota Condo < 1 Mile To Beach!
1 2apartment, Siesta Key
This apartment in Siesta Key's South Village is located within 1 mile of Crescent Beach and Siesta Key Beach, and a 10-minute walk from Point of Rocks and Siesta Key Marina.
Guests can enjoy a marina, outdoor pool, barbecue grills, complimentary WiFi in public areas, and free self-parking, with a fully equipped kitchen, patio, and TV for a comfortable stay.
Guests can enjoy a marina, outdoor pool, barbecue grills, complimentary WiFi in public areas, and free self-parking, with a fully equipped kitchen, patio, and TV for a comfortable stay.

Siesta Beach, Sarasota
10/14 – 10/21
$459/nighttotal: $3213 (7 )
Our House At The Beach, East Tower, 5th Fl
1 2house, Siesta Key
This Siesta Key beachfront home is a 6-minute walk from Siesta Key Beach and a 700-yard walk from Crescent Beach, offering easy access to the area's beautiful beaches. The property has received excellent ratings for location, cleanliness, and user experience.
The vacation home spans 1700 square feet and features a spacious layout with a seating area, a bathroom, and modern amenities like free Wi-Fi, a satellite TV, a washing machine, a dishwasher, an oven, and a private parking space. Guests can enjoy a private swimming pool, a tennis court, a garden, and a terrace or balcony.
The vacation home spans 1700 square feet and features a spacious layout with a seating area, a bathroom, and modern amenities like free Wi-Fi, a satellite TV, a washing machine, a dishwasher, an oven, and a private parking space. Guests can enjoy a private swimming pool, a tennis court, a garden, and a terrace or balcony.

Siesta Beach, Sarasota
10/14 – 10/21
$431/nighttotal: $3017 (7 )
Jamaica Royale Beach Happiness
1 2apartment, Siesta Key
This condo is located in Siesta Key, a 15-minute walk from Siesta Key Beach and St. Boniface Episcopal Church Labyrinth, with Crescent Beach also nearby.
This accommodation offers an outdoor pool, tennis court, onsite marina, barbecue grills, and complimentary self-parking, with wired internet available in common areas.
This accommodation offers an outdoor pool, tennis court, onsite marina, barbecue grills, and complimentary self-parking, with wired internet available in common areas.

Siesta Beach, Sarasota
10/14 – 10/21
$336/nighttotal: $2352 (7 )
Casa Mar By Beachside Management
1 2house, Siesta Key
Casa Mar apartments in Sarasota offer convenient access to Crescent Beach (an 8-minute walk) and Siesta Key Beach (1.1 miles), plus proximity to Sarasota Bradenton International Airport (11 miles).
This 7-guest rental features a fully equipped kitchen with a dishwasher, free Wi-Fi, air conditioning, private entrance, and free on-site parking.
This 7-guest rental features a fully equipped kitchen with a dishwasher, free Wi-Fi, air conditioning, private entrance, and free on-site parking.

Siesta Beach, Sarasota
10/14 – 10/21
$220/nighttotal: $1540 (7 )
The Capri At Siesta
1 2resort, Siesta Key
The Capri at Siesta is located just steps from Siesta Key Beach, a short drive from downtown Siesta Key and popular attractions like Selby Botanical Gardens and Stoneybrook Golf Club. The resort is highly rated for its location, cleanliness, and overall experience.
The resort offers a variety of spacious villas with full kitchens, perfect for families or groups. Guests can enjoy the heated outdoor pool, courtyard garden, barbecue equipment, and beach amenities.
The resort offers a variety of spacious villas with full kitchens, perfect for families or groups. Guests can enjoy the heated outdoor pool, courtyard garden, barbecue equipment, and beach amenities.

Siesta Beach, Sarasota
08/22 – 08/28
$247/nighttotal: $1482 (6 )
Jamaica Royale Villa 41
1 4apartment, Siesta Key
This Siesta Key condo, located in the Jamaica Royale complex, offers a short 2-3 minute walk to Siesta Key Beach and is less than a mile from Siesta Key Village.
The 730-square-foot, one-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen, in-unit laundry, and access to Jamaica Royale's amenities including multiple heated pools and beach access, plus beach chairs and toys are provided.
The 730-square-foot, one-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen, in-unit laundry, and access to Jamaica Royale's amenities including multiple heated pools and beach access, plus beach chairs and toys are provided.

Siesta Beach, Sarasota
08/22 – 08/28
$325/nighttotal: $1950 (6 )
Siesta Key's Premier Location With Amazing Beach View!
2 4apartment, Siesta Key
This Siesta Key apartment is located just steps from the beach, offering a peaceful escape in a less crowded section of the island, within easy walking distance of the village's restaurants, shops, and entertainment. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The 1080-square-foot apartment comfortably accommodates up to 5 guests with two bedrooms and two bathrooms. The apartment features a fully equipped kitchen, a spacious living room with a vintage wine bar, and a private outdoor seating area with a garden water fountain. This Siesta Key rental also includes a carport and guest parking, a storage closet with beach essentials, and a stunning view of the Gulf of Mexico and Siesta Key Beach from the enclosed lanai.
The 1080-square-foot apartment comfortably accommodates up to 5 guests with two bedrooms and two bathrooms. The apartment features a fully equipped kitchen, a spacious living room with a vintage wine bar, and a private outdoor seating area with a garden water fountain. This Siesta Key rental also includes a carport and guest parking, a storage closet with beach essentials, and a stunning view of the Gulf of Mexico and Siesta Key Beach from the enclosed lanai.

Siesta Beach, Sarasota
08/22 – 08/28
$282/nighttotal: $1692 (6 )
Luxury Zen Den With Heated Pool Just Off Siesta Key
2 4apartment, Siesta Key
The Zen Den is a short drive from Siesta Key, located in Sarasota, just 6 miles from the Sarasota Opera and 9.4 miles from the John and Mable Ringling Museum of Art. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The Zen Den is a comfortable and well-equipped rental with a private pool, a patio with pool views, a fully equipped kitchen, and streaming services. Guests can enjoy diving nearby, relaxing on the sun terrace, and unwinding in the peaceful garden setting.
The Zen Den is a comfortable and well-equipped rental with a private pool, a patio with pool views, a fully equipped kitchen, and streaming services. Guests can enjoy diving nearby, relaxing on the sun terrace, and unwinding in the peaceful garden setting.

Siesta Beach, Sarasota
08/22 – 08/28
$292/nighttotal: $1752 (6 )
Siesta Beach Condo Rental With Direct Beach And Pool Access
2 4apartment, Siesta Key
This Siesta Key condo provides direct private beach access within steps and is located a quarter-mile from Siesta Key Public Beach and Siesta Key Village.
This 780 sq ft apartment sleeps up to 5 guests and features 2 bedrooms, 1 bathroom, a full kitchen, air conditioning, a swimming pool, spa, and parking, with complimentary access to heated community pool and on-site laundry facilities.
This 780 sq ft apartment sleeps up to 5 guests and features 2 bedrooms, 1 bathroom, a full kitchen, air conditioning, a swimming pool, spa, and parking, with complimentary access to heated community pool and on-site laundry facilities.

Siesta Beach, Sarasota
10/14 – 10/21
$458/nighttotal: $3206 (7 )
Anchorage Resort 2 Bedroom Condo 6th Flr, Beach Access, Pool 2 Condo
1 2resort, Siesta Key
The Anchorage Resort 2 Bedroom Condo 6th Flr, Beach Access, Pool 2 Condo offers a prime location in Siesta Key's South Village, within a 15-minute walk to Crescent Beach and Siesta Key Beach, and less than 1 mile from Siesta Key Marina and Point of Rocks.
This 2-bedroom condo features complimentary WiFi, a Smart TV, an in-unit washing machine, and access to an on-site outdoor tennis court and barbecue grills.
This 2-bedroom condo features complimentary WiFi, a Smart TV, an in-unit washing machine, and access to an on-site outdoor tennis court and barbecue grills.

Siesta Beach, Sarasota
08/22 – 08/28
$335/nighttotal: $2010 (6 )
Luxury 5 Star Apartment On The Anchorage, Siesta Key Apartment 1018
2 4apartment, Siesta Key
This Siesta Key apartment is just a 10-minute walk from both Crescent Beach and Siesta Key Marina, putting you right in the heart of the action. The apartment boasts excellent ratings for location, cleanliness, and overall user experience.
The two-bedroom, two-bathroom unit comfortably sleeps six guests. You'll enjoy amenities like a swimming pool, fitness center, and tennis court, as well as a balcony, garden, and sauna.
The two-bedroom, two-bathroom unit comfortably sleeps six guests. You'll enjoy amenities like a swimming pool, fitness center, and tennis court, as well as a balcony, garden, and sauna.

Siesta Beach, Sarasota
08/22 – 08/28
$283/nighttotal: $1698 (6 )
Private Balcony, Community Amenities, Beach Access! Our House At The Beach W-203
2 4apartment, Siesta Key
This beachfront Siesta Key condo offers direct access to Siesta Key Beach, a 10-minute walk from Siesta Key Beach Playground, and under a mile from the Siesta Key Farmers Market and St. Boniface Episcopal Church Labyrinth.
The 1190-square-foot rental boasts three bedrooms plus a sofa bed, accommodating multiple guests, and features a private balcony, fully equipped kitchen, swimming pool, spa, tennis court, and parking.
The 1190-square-foot rental boasts three bedrooms plus a sofa bed, accommodating multiple guests, and features a private balcony, fully equipped kitchen, swimming pool, spa, tennis court, and parking.













