Holiday Rentals in Siesta Key, FL

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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

Best Value 2br  Walk To Beach, Dining & Nightlife - Siesta Key, FL
9.8 18 reviews
Siesta Key, FL
01/08 – 06/08
SG$474/nighttotal: SG$2370 (5 )

Best Value 2br Walk To Beach, Dining & Nightlife

2 5
apartment , Siesta Key
This Siesta Key beachfront apartment is less than 1.6km from Crescent Beach and Siesta Key Beach, and around 3.2km from Turtle Beach.
Sleeping up to eight guests, this two-bedroom flat boasts a private balcony, free Wi-Fi, on-site parking, and a kitchen equipped with a fridge and microwave.
97 M² House ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
10 1 review
Siesta Key, FL
06/07 – 13/07
SG$256/nighttotal: SG$1792 (7 )

97 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 3
house , Siesta Key
This Sarasota dwelling is located close to Siesta Key and Lido Key beaches, offering convenient access to coastal attractions within 5 kilometres.
This family-friendly property spans 96 square metres and accommodates up to six guests, featuring two bedrooms, two bathrooms, a well-equipped kitchen, a dedicated workspace, and an expansive backyard with Smart TVs and provided beach chairs.
112 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 1 review
Siesta Key, FL
06/07 – 13/07
SG$333/nighttotal: SG$2331 (7 )

112 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

2 4
apartment , Siesta Key
This two-bedroom flat in the Gulf & Bay Club Bayside community offers direct intercoastal waterway frontage, providing views of marine life and is a short 500-meter walk from Siesta Key Village and the beach.
This 111-square-meter apartment accommodates up to four guests and features resort-style amenities including two heated swimming pools, tennis and pickleball courts, a fitness centre, and secure garage parking.
Newly Renovated Condo Steps From Sk Private Beach - Siesta Key, FL
9.7 113 reviews
Siesta Key, FL
08/07 – 10/07
SG$807/nighttotal: SG$1614 (2 )

Newly Renovated Condo Steps From Sk Private Beach

1 4
apartment , Siesta Key
This Siesta Key townhouse, a minute's walk (less than 0.2 km) from the private beach access on Siesta Key Beach and a short trolley ride from Siesta Key Village, offers convenient access to both the beach and local amenities.
The two-storey property sleeps six guests, boasting two bedrooms (one king, one with two double beds), two bathrooms, a fully equipped eat-in kitchen, and provides beach toys, a wagon, and cooler for guest use.

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

Your Modern Beachside Getaway! - Siesta Key, FL
9.9 151 reviews
Siesta Key, FL
01/07 – 03/07
SG$456/nighttotal: SG$912 (2 )

Your Modern Beachside Getaway!

1 3
apartment , Siesta Key
This Siesta Key beachfront flat is a three-minute walk from Siesta Key Beach and directly opposite numerous restaurants and shops.
The newly remodelled one-bedroom apartment sleeps four, boasting a modern kitchen, hotel-quality bed, and access to a communal pool, patio, courtyard, and barbecue area; on-site parking is also provided.
Anchorage Resort 2 Bedroom Condo With Beach Access - Siesta Key, FL
9.0 4 reviews
Siesta Key, FL
04/07 – 09/07
SG$447/nighttotal: SG$2235 (5 )

Anchorage Resort 2 Bedroom Condo With Beach Access

1 3
apartment , Siesta Key
This Anchorage Resort condo offers private beach access to Crescent Beach on Southern Siesta Key, with the Siesta Key Trolley stopping directly outside for convenient travel to Siesta Key Village.
This two-bedroom, two-bathroom apartment accommodates up to six guests and boasts a fully equipped kitchen, a spacious balcony with canal views, and access to the resort's extensive amenities including the largest community pool on the Key and tennis courts, alongside complimentary beach supplies.
Seashell Esta  Luxe Siesta Key Escape - Siesta Key, FL
10 2 reviews
Siesta Key, FL
04/08 – 05/08
SG$4318/nightfor 1 night

Seashell Esta Luxe Siesta Key Escape

7 4
apartment , Siesta Key
This luxury Siesta Key holiday home is situated in Siesta Key Village, a 2-minute walk from Siesta Key Beach and close to local dining and shopping establishments.
Boasting 7 bedrooms and 8 bathrooms, this expansive property accommodates up to 20 guests and features a resort-style backyard with a heated lagoon-style pool, spa, waterslide, a rooftop deck with Gulf views, elevator access to all three levels, and is equipped with beach essentials.
111 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 11 reviews
Siesta Key, FL
27/06 – 04/07
SG$285/nighttotal: SG$1995 (7 )

111 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

2 2
apartment , Siesta Key
This apartment is located on Siesta Key's bay side, south of Sarasota, offering private access to Siesta Key Beach and a 5-10 minute walk to Siesta Village's shops and restaurants.
This 111 square meter condominium sleeps four guests in two bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and a terrace, with beach chairs and toys provided for your use.

Frequently asked questions about holiday rentals in Siesta Key, FL

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Best Siesta Key, FL holiday rentals with a balcony

Welcome To Your Happy Placeaka Where Real Life Takes A Vacation. - Siesta Key, FL
8.6 7 reviews
Siesta Key, FL
04/07 – 08/07
SG$506/nighttotal: SG$2024 (4 )

Welcome To Your Happy Placeaka Where Real Life Takes A Vacation.

2 4
apartment , Siesta Key
This Siesta Key condo is conveniently located within a 2.4km walk of Crescent Beach and Siesta Key Beach, and 3.4km from Turtle Beach.
This 121 square metre self-catering apartment sleeps six guests, boasting three bedrooms, two bathrooms, a terrace, swimming pool, jacuzzi, tennis court, and free Wi-Fi; nearby attractions include an on-site arcade.
Gertrude's Siesta | 8-steps To Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets - Siesta Key, FL
Siesta Key, FL
04/07 – 11/07
SG$2563/nighttotal: SG$17941 (7 )

Gertrude's Siesta | 8-steps To Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets

5 12
apartment , Siesta Key
This five-bedroom, three-bathroom holiday flat in Siesta Key offers exclusive beach access (#13) just across the street and is a mere 4-minute walk from entertainment, dining, and live music venues, with Point of Rocks reef located 60 metres away.
This spacious accommodation, ideal for up to 18 guests, provides a car-free holiday experience with provided beach gear, including towels, chairs, umbrellas, bikes, and paddleboards, alongside secluded alfresco lounging areas and hammocks for relaxation.
Mandevilla | Pet Friendly Home Located In Siesta Key Village W/ Heated Pool, Walk To Beach! - Siesta Key, FL
9.5 105 reviews
Siesta Key, FL
31/08 – 02/09
SG$768/nighttotal: SG$1536 (2 )

Mandevilla | Pet Friendly Home Located In Siesta Key Village W/ Heated Pool, Walk To Beach!

1 2
apartment , Siesta Key
This Siesta Key house is located in the village, just a short distance from popular beaches, restaurants and attractions. It has received excellent ratings for location, cleanliness and overall user experience.
The property offers a fully equipped kitchen, a comfortable living area and a laundry machine. Guests can enjoy outdoor grilling, a swimming pool, a terrace and a garden, making it a perfect place to relax and enjoy the Florida sunshine.
6415 Midnight Pass #707 - Siesta Key, FL
9.0 1 review
Siesta Key, FL
01/08 – 06/08
SG$474/nighttotal: SG$2370 (5 )

6415 Midnight Pass #707

2 5
house , Siesta Key
This Siesta Key holiday home, 6415 Midnight Pass #707, is a 7-minute walk from Crescent Beach, 2.6km from Turtle Beach, and 2.9km from Siesta Key Beach, offering convenient access to Siesta Key's famed sands.
The 116 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, Jacuzzi, sauna, fitness centre, and tennis court, alongside a fully equipped kitchen and free Wi-Fi.

Best Siesta Key, FL holiday rentals with parking

102 M² House ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 44 reviews
Siesta Key, FL
04/07 – 11/07
SG$327/nighttotal: SG$2289 (7 )

102 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 4
house , Siesta Key
This bayside apartment in the Midnight Cove 1 community on Siesta Key, Florida, offers easy walking access to Crescent Beach and is close to Siesta Key Village and Sarasota.
The 102-square-metre (1100 sq ft) property sleeps four guests in two bedrooms and two bathrooms, boasting a gourmet kitchen, a private terrace, a swimming pool, and access to tennis courts; nearby attractions include discounted water sports rentals and free Siesta Key trolleys.
Siesta Key Gulf Front Condo - Siesta Key, FL
9.9 149 reviews
Siesta Key, FL
29/12 – 31/01
SG$479/nighttotal: SG$15807 (33 )

Siesta Key Gulf Front Condo

2 2
apartment , Siesta Key
This two-bedroom apartment is located in the Crescent Royale Condominiums on Siesta Key, just a short walk from the beach, widely considered the best in the USA. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
This 119 square metre apartment comfortably accommodates up to six guests. The property offers a range of amenities, including a swimming pool, Jacuzzi, fitness centre, and a private carport with dedicated parking.
Polynesian Gardens Villa: Renovated, Near Crescent Beach, Pool, Patio & Modern Comforts! - Siesta Key, FL
9.3 19 reviews
Siesta Key, FL
04/07 – 11/07
SG$432/nighttotal: SG$3024 (7 )

Polynesian Gardens Villa: Renovated, Near Crescent Beach, Pool, Patio & Modern Comforts!

2 4
apartment , Siesta Key
This two-bedroom apartment is situated directly on the beach, just a 2.4 km walk from Siesta Key Beach and Crescent Beach, and within 1.6 km of Siesta Key Marina and St. Boniface Episcopal Church Labyrinth.
The 104 square metre apartment offers a comfortable stay for up to four guests with amenities such as a swimming pool, a terrace, a garden, and free parking.
Siesta Key Condo: Resort Amenities, Walk To Beach! - Siesta Key, FL
9.2 98 reviews
Siesta Key, FL
25/12 – 02/01
SG$551/nighttotal: SG$4408 (8 )

Siesta Key Condo: Resort Amenities, Walk To Beach!

2 5
house , Siesta Key
This Siesta Key apartment is located just 500 metres from Crescent Beach, a short drive from Siesta Key Beach and Turtle Beach, and within a 32-kilometre drive of the John and Mable Ringling Museum of Art. The apartment has been rated excellent for location, cleanliness and by previous guests.
This two-bedroom apartment spans 84 square metres and comfortably accommodates up to six guests. The apartment offers a range of amenities including a swimming pool, spa, fitness centre, tennis court, and a private balcony with outdoor dining area.
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