Holiday Rentals in Siesta Key, FL

5754 available vacation rental offers

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Siesta Key, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Siesta Key, FL

Best family friendly Siesta Key, FL holiday rentals

Among the 5754 accommodations in Siesta Key, FL, here are the 4 best family friendly rentals

16 Guest Pool House Walk To The Beach And Village - Siesta Key, FL
9.7 76 reviews
Siesta Key, FL
04/07 – 07/07
SG$4122/nighttotal: SG$12366 (3 )

16 Guest Pool House Walk To The Beach And Village

6 1
apartment , Siesta Key
This Siesta Key house is situated just under 3 kilometres from Siesta Key Beach, and within 5 kilometres of both Shell Beach and Crescent Beach. It is located in Siesta Key Village, a quiet and relaxing area, offering a peaceful retreat from the hustle and bustle of more crowded areas. Guests have rated this property excellent for location, cleanliness and overall experience.
The property is a 6-bedroom house that provides ample space for large families or groups of friends. It offers modern amenities, including free Wi-Fi, a fully equipped kitchen, a private pool, a fenced private yard, and barbecue grills.
Beautiful 2025 Renovated - 550 Sq Ft  Patio - Across Street From Beach - Siesta Key, FL
9.2 40 reviews
Siesta Key, FL
21/06 – 28/06
SG$668/nighttotal: SG$4676 (7 )

Beautiful 2025 Renovated - 550 Sq Ft Patio - Across Street From Beach

2 3
apartment , Siesta Key
This beachfront Siesta Key condo offers direct access to Siesta Key Beach, a short walk from St. Boniface Episcopal Church Labyrinth and within 3.2km of Crescent Beach and Siesta Key Beach Playground.
The 164 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a private pool, fully equipped kitchen, fitness centre, sauna, and tennis court.
Siesta Key Dream Vacation - Siesta Key, FL
9.7 189 reviews
Siesta Key, FL
01/08 – 08/08
SG$401/nighttotal: SG$2807 (7 )

Siesta Key Dream Vacation

2 2
apartment , Siesta Key
This two-bedroom apartment is located on Siesta Key, just a 5-minute walk from Crescent Beach and 2 kilometres from Siesta Key Beach. The apartment is highly rated by previous guests, with excellent scores for location, cleanliness, and overall experience.
The 130 square metre apartment comfortably accommodates up to 6 guests and features a fully equipped kitchen, a private pool, a terrace, and a garden. The apartment also has a range of amenities including air conditioning, Wi-Fi, a washing machine, and a dryer, as well as free parking.
Florida Charm, Bayside, Pool, Tiki, Steps To Beach - Siesta Key, FL
8.6 10 reviews
Siesta Key, FL
19/06 – 21/06
SG$683/nighttotal: SG$1366 (2 )

Florida Charm, Bayside, Pool, Tiki, Steps To Beach

2 4
apartment , Siesta Key
This Siesta Key beachfront apartment is located near Siesta Key Beach and Crescent Beach, within 2km of St Boniface Episcopal Church Labyrinth, Siesta Key Beach Playground, and Siesta Key Marina.
The 70 square metre property offers two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and access to a swimming pool, spa, and concierge services.

Best Siesta Key, FL holiday rentals with a pool

Among the 5754 accommodations in Siesta Key, FL, here are the 4 best rentals with a pool

Bay Oaks Ground Floor - Siesta Key, FL
9.5 112 reviews
Siesta Key, FL
23/12 – 28/12
SG$395/nighttotal: SG$1975 (5 )

Bay Oaks Ground Floor

2 2
house , Siesta Key
This holiday home is situated just a short walk from Crescent Beach and a little over a mile from Siesta Key Beach, offering a prime location for a relaxing beach getaway. The property has received excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom property is 80 square metres in size and offers comfortable accommodation for families or small groups. The home comes equipped with a fully fitted kitchen, air conditioning, a private swimming pool, a tennis court, and a garden, providing everything you need for a comfortable and enjoyable stay.
Cottage On Siesta Key
Beachside & Stunning Sunsets - Siesta Key, FL
9.8 161 reviews
Siesta Key, FL
21/07 – 24/07
SG$375/nighttotal: SG$1125 (3 )

Cottage On Siesta Key Beachside & Stunning Sunsets

1 2
cottage , Siesta Key
This Siesta Key apartment is just a short walk from Crescent Beach, a popular beach known for its soft, white sand, and is close to shops, restaurants, and cafes. It receives excellent ratings for location, cleanliness, and overall user experience.
The apartment has one bedroom and one bathroom and can accommodate up to four guests. It offers a range of amenities including a kitchen with a fridge, freezer, microwave, and dishwasher, a swimming pool, a garden, parking, and free Wi-Fi.
Siesta Villa Laughing Gull - Siesta Key, FL
9.8 58 reviews
Siesta Key, FL
22/06 – 27/06
SG$513/nighttotal: SG$2565 (5 )

Siesta Villa Laughing Gull

2 2
house , Siesta Key
This house is located in Siesta Key, within walking distance of Crescent Beach and a short drive from Siesta Key Beach. It has received excellent ratings for location, cleanliness, and overall user experience.
The house has three bedrooms and can accommodate up to five guests. You can enjoy features such as a fully equipped kitchen, air conditioning, a private terrace, a swimming pool, and free parking.
Bay View Condo, Minutes To Top Beach In The Us - Siesta Key, FL
9.2 49 reviews
Siesta Key, FL
06/07 – 13/07
SG$212/nighttotal: SG$1484 (7 )

Bay View Condo, Minutes To Top Beach In The Us

2 2
apartment , Siesta Key
This Siesta Key beachfront apartment offers stunning views and is a short walk (less than 2.4km) from both Siesta Key Beach and Crescent Beach, with Turtle Beach a 4.5km drive away.
The two-bedroom, one-bathroom flat sleeps four guests and includes air conditioning, a swimming pool, parking, and complimentary Wi-Fi; enjoy the smoke-free environment and direct waterfront access.

Frequently asked questions about holiday rentals in Siesta Key, FL

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Best Siesta Key, FL holiday rentals with a balcony

Peaceful Siesta Key Condo - Short Stroll To The Beach - Gbb 1219 - Siesta Key, FL
10 3 reviews
Siesta Key, FL
08/07 – 14/07
SG$487/nighttotal: SG$2922 (6 )

Peaceful Siesta Key Condo - Short Stroll To The Beach - Gbb 1219

2 4
apartment , Siesta Key
This beachfront apartment is situated near Siesta Key Beach, a 15-minute walk from St. Boniface Episcopal Church Labyrinth and under 3.2km from Crescent Beach.
This 119 square metre, two-bedroom, two-bathroom property sleeps four, boasting a fully equipped kitchen, private terrace, swimming pool, sauna, fitness centre, tennis court, and free Wi-Fi; BBQ facilities are also available.
Palm Bay 5th Floor On The Beach \Nsunsets From The Open Lanai, Two Queen Beds. - Siesta Key, FL
9.7 117 reviews
Siesta Key, FL
04/07 – 07/07
SG$847/nighttotal: SG$2541 (3 )

Palm Bay 5th Floor On The Beach \Nsunsets From The Open Lanai, Two Queen Beds.

1 1
apartment , Siesta Key
This Siesta Key beachfront apartment, less than 1.6km from Siesta Key Beach, Crescent Beach, and Siesta Key Marina, offers direct beach access and proximity to local attractions.
The one-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, swimming pool, Jacuzzi, fitness centre, tennis court, and spa, plus on-site parking.
Condo# 410- Beautiful - Siesta Key, FL
9.0 4 reviews
Siesta Key, FL
19/07 – 01/08
SG$346/nighttotal: SG$4498 (13 )

Condo# 410- Beautiful

2 4
apartment , Siesta Key
This Siesta Key condo, situated within La Siesta Condominiums, offers easy walking access to Siesta Village and Siesta Key Public Beach.
The 81 square metre (870 square foot) apartment features two bedrooms, one bathroom, sleeps six, and includes access to a swimming pool, tennis court, and fitness centre, plus a screened lanai.
Lovely 2bd Condo Close To The Beach (An1145) - Siesta Key, FL
Siesta Key, FL
17/06 – 26/06
SG$574/nighttotal: SG$5166 (9 )

Lovely 2bd Condo Close To The Beach (An1145)

2 6
apartment , Siesta Key
This private eighth-floor condominium in Siesta Key's South Village offers direct access to Crescent Beach, just across the street, and is a short walk from Siesta Key Beach and Siesta Key Village, with complimentary trolley service available. This two-bedroom, two-bathroom apartment accommodates up to six guests and features a fully equipped kitchen, air conditioning, a swimming pool, a balcony with north-western views, and includes four beach chairs, towels, an umbrella, a cooler, and a beach cart for your convenience.

Best Siesta Key, FL holiday rentals with parking

Condo# 405 2 Bed/1 Bath Condo Steps To Siesta Key Beach! - Siesta Key, FL
9.6 15 reviews
Siesta Key, FL
18/07 – 25/07
SG$403/nighttotal: SG$2821 (7 )

Condo# 405 2 Bed/1 Bath Condo Steps To Siesta Key Beach!

2 2
apartment , Siesta Key
This Siesta Key apartment, located in the La Siesta Condominiums, is steps from Siesta Key Beach and a short walk from Siesta Village.
The 81-square-metre (870 sq ft) property offers two bedrooms, one bathroom, sleeps up to six guests, and includes a fully equipped kitchen, private Wi-Fi, and access to a swimming pool, fitness centre, and tennis court.
Clean, Modern And Newly Renovated Condo On Us #1 Private Siesta Key Beach - Siesta Key, FL
9.8 241 reviews
Siesta Key, FL
21/07 – 24/07
SG$453/nighttotal: SG$1359 (3 )

Clean, Modern And Newly Renovated Condo On Us #1 Private Siesta Key Beach

1 2
apartment , Siesta Key
This Siesta Key apartment is situated less than 2km from Siesta Key Beach and Crescent Beach, also within 1.6km of Siesta Key Marina and St Boniface Episcopal Church Labyrinth.
Offering a one-bedroom, one-bathroom flat with a private pool, free WiFi, fully equipped kitchen, and access to a shared garden and barbecue facilities, this pet-friendly property sleeps up to two guests and includes a patio and Smart TV.
Crescent Beach 1011 #3 - Siesta Key, FL
9.3 727 reviews
Siesta Key, FL
25/10 – 01/11
SG$255/nighttotal: SG$1785 (7 )

Crescent Beach 1011 #3

1 2
house , Siesta Key
This charming house is located directly on Crescent Beach in Siesta Key, just a short drive from Turtle Beach. It has received excellent ratings for location, cleanliness and overall experience.
The house has two bedrooms, a living room, a fully equipped kitchen and two bathrooms. It features air conditioning, a dishwasher, a TV and a private swimming pool, as well as a terrace and a garden.
The Ringling Beach House - Siesta Key, FL
8.7 908 reviews
Siesta Key, FL
19/06 – 21/06
SG$1060/nighttotal: SG$2120 (2 )

The Ringling Beach House

2 6
resort , Siesta Key
The Ringling Beach House is directly opposite the world-renowned Siesta Key Beach, with the lively Siesta Key Village just an 8-minute walk away, offering a perfect blend of beachside relaxation and easy access to shops and restaurants. This apartment complex has consistently received very good ratings for cleanliness and user experience, and an excellent rating for its location.
Each apartment is individually decorated with a choice of leather, dark wood, or patterned furnishings, creating a unique and comfortable atmosphere. Guests can enjoy a refreshing outdoor community pool, barbecue facilities, and complimentary beach chairs, making it easy to relax and enjoy the beautiful Florida weather.
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