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

Heated Pool-short Walk To Beach, Free Trolley Around Siesta Key! - Siesta Key, FL
9.3 27 reviews
Siesta Key, FL
27/06 – 04/07
SG$350/nighttotal: SG$2450 (7 )

Heated Pool-short Walk To Beach, Free Trolley Around Siesta Key!

2 2
apartment, Siesta Key
This apartment is situated in Siesta Key, just a short walk from Crescent Beach and a little over 1.6 kilometres from Siesta Key Beach. The apartment has received very good user ratings, with excellent reviews for its location and cleanliness.
The apartment is a two-bedroom property, covering 102 square metres and accommodating up to four guests. Guests can enjoy a range of amenities, including a swimming pool, tennis court, sauna, and a garden, as well as a balcony with pool views.
[Beach Elements] Pool View + Private Beach & Bikes - Siesta Key, FL
9.6 341 reviews
Siesta Key, FL
27/06 – 30/06
SG$386/nighttotal: SG$1158 (3 )

[Beach Elements] Pool View + Private Beach & Bikes

1 2
apartment, Siesta Key
This Siesta Key apartment is just a short walk (around 0.5km) from the beautiful beach and a short drive (around 2km) from the bustling Siesta Key Village. The apartment consistently receives excellent ratings for its location, cleanliness, and overall user experience.
This studio apartment can accommodate up to three guests and features a fully equipped kitchen with granite countertops and stainless steel appliances. Enjoy the convenience of a private patio, community BBQ area, laundry facilities, and beach cruiser bike rentals (for an additional fee), as well as provided beach chairs and other amenities.
Gertrude's Siesta | Pool, Jacuzzi! 1-minute To Beach! 4-min Dining & Music! - Siesta Key, FL
10 2 reviews
Siesta Key, FL
04/07 – 11/07
SG$1674/nighttotal: SG$11718 (7 )

Gertrude's Siesta | Pool, Jacuzzi! 1-minute To Beach! 4-min Dining & Music!

4 12
apartment, Siesta Key
This Siesta Key holiday home is situated less than 1.6km from Crescent Beach and Siesta Key Beach, and approximately 3.5km from Turtle Beach, offering easy access to these renowned stretches of sand.
This five-bedroom, four-bathroom property boasts 167 square metres of living space, comfortably accommodating up to 16 guests and including a private swimming pool, terrace, and fully equipped kitchen with gas grills.
Modern Bright Escape Mins Beach, Pool, Hot Tub - Siesta Key, FL
9.0 2 reviews
Siesta Key, FL
14/07 – 16/07
SG$431/nighttotal: SG$862 (2 )

Modern Bright Escape Mins Beach, Pool, Hot Tub

1 2
apartment, Siesta Key
This Siesta Key apartment, an eight-minute walk from Crescent Beach, is 11.6km from Marina Jack and 17.7km from the Ringling Museum.
The 70-square-metre self-catering flat offers one bedroom, one bathroom, sleeps ten guests, and includes a private pool, hot tub, free Wi-Fi, and parking.
186 M² House ∙ 4 Bedrooms ∙ 12 Guests - Siesta Key, FL
9.8 34 reviews
Siesta Key, FL
05/07 – 11/07
SG$1194/nighttotal: SG$7164 (6 )

186 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 12
house, Siesta Key
Casa Mahalo, a spacious duplex in Siesta Key Village, is located a 0.32-kilometre walk from the world-renowned Siesta Key Beach.
This four-bedroom, three-bathroom property boasts 185 square metres of living space, a private heated pool (heated Nov 15th - Apr 15th), private cabana, two-car garage, and accommodates up to 12 guests, offering beach essentials and enhanced cleaning protocols.
Walk To Everything! Beach, Nightlife & Heated Pool - Siesta Key, FL
10 3 reviews
Siesta Key, FL
14/07 – 11/08
SG$197/nighttotal: SG$5516 (28 )

Walk To Everything! Beach, Nightlife & Heated Pool

2 3
apartment, Siesta Key
This two-bedroom, two-bathroom apartment is situated on the southern end of Siesta Key, Florida, a short 0.8-1.1km walk from Crescent Beach accesses #12 & #13 and approximately 1.6km from Siesta Key Village.
Sleeping six guests, the self-catering flat offers a king and two queen beds, a full kitchen, private carport parking, and access to a heated pool, clubhouse, and Xplorie's complimentary daily attraction passes (bike, kayak rental, dolphin cruise, or Ringling Museum).
Spacious 2br 2nd Floor Siesta Key Condo - Gbb 1274 - Siesta Key, FL
9.6 5 reviews
Siesta Key, FL
27/06 – 03/07
SG$403/nighttotal: SG$2418 (6 )

Spacious 2br 2nd Floor Siesta Key Condo - Gbb 1274

2 3
apartment, Siesta Key
This second-floor condominium in the Gulf and Bay Club Bayside offers a tranquil Key West-style setting, just a 300-metre walk from Siesta Key/Crescent Beach, and is conveniently located near popular attractions such as St. Armands Circle and the Mall at University Town Centre.
This 119 square metre apartment, accommodating up to four guests, features two bedrooms and two bathrooms, complete with a fully equipped kitchen, air conditioning, a swimming pool, sauna, spa, fitness centre, tennis court, and private parking, whilst also providing beach gear and community gas grills for guest use.
Bayside Paradise On Siesta Key Awaits You! Ready To Relax? - Siesta Key, FL
9.0 70 reviews
Siesta Key, FL
01/11 – 10/11
SG$204/nighttotal: SG$1836 (9 )

Bayside Paradise On Siesta Key Awaits You! Ready To Relax?

2 2
apartment, Siesta Key
This Siesta Key apartment, a short 1.2km stroll from Siesta Key Beach and Crescent Beach, offers convenient proximity to Siesta Key Marina and St. Boniface Episcopal Church Labyrinth.
The 64 square metre self-catering property sleeps four guests in two bedrooms and one bathroom, boasting a private patio, swimming pool, jacuzzi, tennis court, and fully equipped kitchen including a dishwasher and washing machine.
Siesta Key Village-suite #1: A Block To The Beach! - Siesta Key, FL
9.8 125 reviews
Siesta Key, FL
02/07 – 04/07
SG$485/nighttotal: SG$970 (2 )

Siesta Key Village-suite #1: A Block To The Beach!

1 3
apartment, Siesta Key
This Siesta Key apartment is just 0.6 kilometres from the famous Siesta Key Beach and 1.3 kilometres from Crescent Beach, making it a perfect base for exploring the area. The apartment has consistently received excellent reviews for its location, cleanliness, and overall experience.
The apartment is a one-bedroom flat with a floor area of 84 square metres. It features a fully equipped kitchen, private parking, outdoor seating, a swimming pool, a tennis court, and laundry service, perfect for families or groups of friends.
Lj's Cottages 1 - Pool Beach Sunset - Siesta Key, FL
9.8 7 reviews
Siesta Key, FL
14/08 – 21/08
SG$548/nighttotal: SG$3836 (7 )

Lj's Cottages 1 - Pool Beach Sunset

2 8
apartment, Siesta Key
This Siesta Key apartment is situated less than 1.6km from Crescent Beach and Siesta Key Beach, and around 3.2km from Turtle Beach, offering easy access to Siesta Key's renowned sands.
The three-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and parking; nearby barbecue grills are available for outdoor use.
Couples Getaway On Siesta Key! - Siesta Key, FL
9.8 64 reviews
Siesta Key, FL
27/06 – 01/07
SG$254/nighttotal: SG$1016 (4 )

Couples Getaway On Siesta Key!

1 2
apartment, Siesta Key
This Siesta Key apartment offers direct beach access to Crescent Beach, located 1.6km north of Stickney Point and 3.2km from Siesta Key Village.
The second-floor flat features a king-sized bed, two 32-inch HDTVs, a private pool, and can comfortably accommodate two guests, with access to on-site amenities including a Tiki Hut and bocci ball court.
Siesta Soul - 334 - Siesta Key, FL
10 2 reviews
Siesta Key, FL
02/07 – 04/07
SG$5483/nighttotal: SG$10966 (2 )

Siesta Soul - 334

3 3
house, Siesta Key
Siesta Soul - 334 is a four-bedroom property on Siesta Key, less than 1.3km from Siesta Key Beach and 2km from Crescent Beach.
This 245 square metre house sleeps 15 guests and boasts a private pool, spa, and free parking, alongside a fully equipped kitchen, three bathrooms, and free Wi-Fi.

Best family friendly Siesta Key, FL holiday rentals

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

6415 Midnight Pass #304 - Siesta Key, FL
Siesta Key, FL
25/12 – 02/01
SG$627/nighttotal: SG$5016 (8 )

6415 Midnight Pass #304

2 5
house, Siesta Key
6415 Midnight Pass #304, a Siesta Key holiday home, is conveniently located a short walk from Crescent Beach and within 3.2km of Siesta Key Beach and Turtle Beach, also close to the John and Mable Ringling Museum of Art (17.7km).
This 116 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private balcony, swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and fully equipped kitchen.
Siesta Heron Suites & Villas - Siesta Key, FL
9.0 737 reviews
Siesta Key, FL
25/06 – 01/07
SG$351/nighttotal: SG$2106 (6 )

Siesta Heron Suites & Villas

1 4
house, Vamo
The Siesta Heron Suites & Villas are located in Siesta Key, just 2.4 kilometres from Crescent Beach and 19.3 kilometres from The John and Mable Ringling Museum of Art. The apartment has received very good user and location ratings, and an excellent rating for cleanliness.
This self-catering property features a well-equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. The apartment also has a balcony or patio with views of the lake and pool, air conditioning, cable TV, a garden, a swimming pool, a spa, parking, and internet access.
Gertrude's Siesta | Ocean-views, Pool, 1-2 Min Walk To Beach, Covered Patio, Private Elevator! - Siesta Key, FL
9.8 86 reviews
Siesta Key, FL
04/07 – 08/07
SG$1735/nighttotal: SG$6940 (4 )

Gertrude's Siesta | Ocean-views, Pool, 1-2 Min Walk To Beach, Covered Patio, Private Elevator!

3 4
apartment, Siesta Key
This Siesta Key holiday home is situated less than 1.6km from Siesta Key Beach and playground, and a short distance from the Siesta Key Farmers Market.
The three-bedroom, three-bathroom property sleeps up to 10 guests and boasts a private swimming pool, terrace, garden, BBQ grills, free Wi-Fi, and a fully equipped kitchen; enjoy on-site water park fun.
Siesta Soul | Multilevel Home Located In Siesta Key Village W/ Private Pool, Fire Pit, Walk To Beach - Siesta Key, FL
9.8 49 reviews
Siesta Key, FL
27/06 – 30/06
SG$1596/nighttotal: SG$4788 (3 )

Siesta Soul | Multilevel Home Located In Siesta Key Village W/ Private Pool, Fire Pit, Walk To Beach

4 2
apartment, Siesta Key
This Siesta Key Village property is less than 1.6km from Siesta Key Beach and the Farmers Market, offering easy access to Siesta Key Beach Playground and Irma Beach within 3.2km.
This four-bedroom, three-bathroom house boasts 245 square metres of living space, including a private pool, Jacuzzi, and fireplace, comfortably accommodating up to eight guests and featuring a fully equipped kitchen and laundry facilities.

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

Jamaica Royale 2br Townhome - Siesta Key, FL
9.0 59 reviews
Siesta Key, FL
02/07 – 04/07
SG$1269/nighttotal: SG$2538 (2 )

Jamaica Royale 2br Townhome

2 3
house, Siesta Key
This Siesta Key townhouse enjoys a prime location, just a short walk from Crescent Beach and within 11-18km of Sarasota attractions such as the Ringling Museum and Sarasota Opera House.
The 132 square metre property offers a fully equipped kitchen, private parking, swimming pool, tennis court, and sleeps up to [Number of guests needs to be added - information not provided], perfect for adults seeking a relaxing Siesta Key getaway.
Sand Dollar Studio Pool Daily Rentals - Siesta Key, FL
Siesta Key, FL
31/08 – 02/09
SG$288/nighttotal: SG$576 (2 )

Sand Dollar Studio Pool Daily Rentals

1 2
studio, Siesta Key
This Siesta Key apartment is located in Sarasota, a 4-minute walk from Crescent Beach and approximately 11-18 kilometres from Sarasota Opera, Marina Jack, and The Ringling Museum.
This 33-square-metre studio apartment sleeps up to three guests and features air conditioning, Wi-Fi, a kitchenette with a fridge and microwave, a private entrance, and access to a garden and swimming pool, with free private parking available.
Your Modern Beachside Getaway! - Siesta Key, FL
9.9 151 reviews
Siesta Key, FL
30/07 – 05/08
SG$323/nighttotal: SG$1938 (6 )

Your Modern Beachside Getaway!

1 2
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.
Charm | Comfy | Tiki | Pool Private Beach - Siesta Key, FL
9.6 282 reviews
Siesta Key, FL
04/07 – 08/07
SG$445/nighttotal: SG$1780 (4 )

Charm | Comfy | Tiki | Pool Private Beach

1 4
apartment, Siesta Key
This Siesta Key apartment is located directly on the beach, within 1.6 kilometres of St. Boniface Episcopal Church Labyrinth and Crescent Beach, and within 3.2 kilometres of Siesta Key Marina and Point of Rocks. The property has been rated excellent for its location, cleanliness and overall experience by previous guests.
The apartment is a one-bedroom, one-bathroom property with a floor area of 53 square metres, comfortably accommodating up to four guests. It features amenities such as a fully-equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, and parking.

Frequently asked questions about holiday rentals in Siesta Key, FL

Destinations nearby

Best Siesta Key, FL holiday rentals with a balcony

Gertrude's Siesta | Private Patio, Pool, Jacuzzi | 1 Min To Beach | 4 Min To Dining & Music! - Siesta Key, FL
10 6 reviews
Siesta Key, FL
02/07 – 05/07
SG$1625/nighttotal: SG$4875 (3 )

Gertrude's Siesta | Private Patio, Pool, Jacuzzi | 1 Min To Beach | 4 Min To Dining & Music!

3 2
apartment, Siesta Key
This non-smoking flat is situated in Siesta Key's South Village, a 4-minute walk from Crescent Beach and a 14-minute walk from Siesta Key Public Beach.
This 70 square metre holiday home accommodates up to five guests across three bedrooms and two bathrooms, featuring a well-equipped kitchen, on-site parking, a communal swimming pool and hot tub, and a private garden, with complimentary Wi-Fi provided.
Johnnys Island Palm | Walk To Siesta Key Beach, Marina, Dining & Pool - Siesta Key, FL
10 5 reviews
Siesta Key, FL
01/08 – 06/08
SG$479/nighttotal: SG$2395 (5 )

Johnnys Island Palm | Walk To Siesta Key Beach, Marina, Dining & Pool

2 5
apartment, Siesta Key
This South Siesta Key apartment is located less than 0.2 km from Captain Curt's and The Daiquiri Deck restaurants, 0.3 km from Siesta Key Beach, and 0.3 km from Siesta Key Marina.
This 120 square metre self-catering property boasts two bedrooms (one king, two queen beds), two bathrooms, a living room with a sofa bed sleeping up to six guests, a private balcony, and access to a shared pool and boat mooring; free Wi-Fi and kitchen essentials are provided.
Beachy Villa On Siesta Key With Heated Pool, Screened In Lanai, And Ground Level - Siesta Key, FL
9.6 88 reviews
Siesta Key, FL
25/06 – 01/07
SG$517/nighttotal: SG$3102 (6 )

Beachy Villa On Siesta Key With Heated Pool, Screened In Lanai, And Ground Level

2 4
house, Siesta Key
This Siesta Key villa is situated just a short walk from the beach and within a 1.1 kilometre radius of shops, restaurants, and grocery stores, making it a convenient base for exploring the area. The property has consistently received excellent ratings for cleanliness, location, and overall user experience.
The two-bedroom villa, spanning 97 square metres, comfortably accommodates up to eight guests. It offers a range of amenities including a private pool, a spa, a garden, a terrace, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
70 M² House ∙ 1 Bedroom ∙ 4 Guests - Siesta Key, FL
10 4 reviews
Siesta Key, FL
23/07 – 26/07
SG$312/nighttotal: SG$936 (3 )

70 M² House ∙ 1 Bedroom ∙ 4 Guests

1 4
house, Sarasota
This Sarasota condo, situated in the desirable Cherokee Park neighbourhood, is minutes from Siesta Key's beaches and a short cycle from Sarasota's city centre.
The 69 square metre, one-bedroom property features a fully equipped kitchen, private yard, screened terrace, community pool and gym access, sleeping up to four guests and including all utilities in the rental price.

Best Siesta Key, FL holiday rentals with parking

Condo# 303 Amazing View Of The Gulf!! Siesta Key At Its Best. - Siesta Key, FL
9.6 8 reviews
Siesta Key, FL
21/07 – 28/07
SG$382/nighttotal: SG$2674 (7 )

Condo# 303 Amazing View Of The Gulf!! Siesta Key At Its Best.

1 4
apartment, Siesta Key
This Siesta Key apartment is a five-minute walk from Siesta Key Beach and Playground, and less than 1.6km from the Siesta Key Farmers Market and St Boniface Episcopal Church Labyrinth.
The 76 square metre self-catering flat offers one bedroom, one bathroom, sleeps four, and includes a private pool, in-unit laundry, and access to a fitness centre, arcade, and barbecue grills.
Extraordinary 2bd Condo Near The Beach (An805) - Siesta Key, FL
9.4 46 reviews
Siesta Key, FL
01/08 – 08/08
SG$460/nighttotal: SG$3220 (7 )

Extraordinary 2bd Condo Near The Beach (An805)

2 5
apartment, Siesta Key
This Siesta Key apartment is situated near Crescent Beach, a 10-minute walk from Siesta Key Marina and less than 1.6km from Siesta Key Beach.
The 116 square metre property boasts two bedrooms, two bathrooms, accommodates six guests, and offers amenities including a swimming pool, tennis court, and free Wi-Fi.
Sunset Royale - 214- Spectacular Views Of Siesta Key Beach - Siesta Key, FL
Siesta Key, FL
04/07 – 09/07
SG$392/nighttotal: SG$1960 (5 )

Sunset Royale - 214- Spectacular Views Of Siesta Key Beach

2 3
apartment, Siesta Key
This Siesta Key condo is located near Siesta Beach, a short walk from Siesta Key Village, offering easy access to the beach and local amenities.
The 86-square-metre (926 sq ft) apartment features two bedrooms, two bathrooms, a kitchen with a fridge, and internet access; guests can also enjoy on-site parking, air conditioning, and a spa, plus nearby opportunities for golfing, watersports, and shopping at St. Armands Circle and the Mall at University Town Centre.
Midnight Cove Ii 931c - Modern Siesta Key Condo Close To Beach And Pool - Siesta Key, FL
9.7 6 reviews
Siesta Key, FL
14/07 – 11/08
SG$265/nighttotal: SG$7420 (28 )

Midnight Cove Ii 931c - Modern Siesta Key Condo Close To Beach And Pool

2 3
apartment, Siesta Key
This apartment is located on Siesta Key, just a 1.6km walk from both Siesta Key Beach and Crescent Beach, and a 1.6km walk from Siesta Key Marina and Point of Rocks. It has received excellent ratings from previous guests.
The self-catering accommodation is a two-bedroom apartment with a fully equipped kitchen, a sofa bed, a washing machine, and two bathrooms. You can enjoy a range of amenities including a swimming pool, a spa, a fitness centre, a tennis court, and a terrace.
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