Holiday Rentals in Siesta Key, FL

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Siesta Key, FL holiday rentals
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5754 Holiday Rentals and Airbnb in Siesta Key, FL

Walk To Beach Condo With Pool And Patio In Sarasota! - Siesta Key, FL
9.2 39 reviews
Siesta Key, FL
01/08 – 08/08
NZ$342/nighttotal: NZ$2394 (7 )

Walk To Beach Condo With Pool And Patio In Sarasota!

2 5
apartment, Siesta Key
This apartment is located in Sarasota, just a short 6-minute walk from Crescent Beach and a 10-minute drive from Siesta Key, offering easy access to the beautiful beaches and vibrant nightlife of the area. The property has received excellent user ratings for cleanliness and location, indicating a comfortable and well-maintained stay.
The apartment has two bedrooms, a living room, and a fully equipped kitchen, covering 84 square metres of space. Guests can enjoy a private patio, a refreshing swimming pool, and a spa, along with free Wi-Fi and parking.
Gertrude Siesta | Budget Friendly, Private Patio, 5-min To Beach, 1-min To Dining & Entertainment! - Siesta Key, FL
Siesta Key, FL
05/07 – 11/07
NZ$906/nighttotal: NZ$5436 (6 )

Gertrude Siesta | Budget Friendly, Private Patio, 5-min To Beach, 1-min To Dining & Entertainment!

3 12
apartment, Siesta Key
This Siesta Key apartment, situated less than 1.6km from Crescent Beach and Siesta Key Beach and around 3.2km from Turtle Beach, offers convenient access to Siesta Key's stunning coastline.
Sleeping up to 12 guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, free Wi-Fi, a swimming pool, on-site water park, and a terrace, making it ideal for families or large groups seeking a self-catering holiday rental near the beach.
Minorga On The Gulf - Siesta Key, FL
9.5 34 reviews
Siesta Key, FL
09/07 – 11/07
NZ$1385/nighttotal: NZ$2770 (2 )

Minorga On The Gulf

1 4
house, Siesta Key
Minorga on the Gulf, a Siesta Key holiday home, is a 7-minute walk from Siesta Key Beach and within 9.6-16 kilometers of Sarasota attractions including the Ringling Museum of Art and Sarasota Opera House.
This self-catering property boasts a fully equipped kitchen, swimming pool, free Wi-Fi, and private parking; it is suitable for adults aged 25 and over.
Walk To Siesta Key Beach & Village | Private Patio | Prime Location! - Siesta Key, FL
9.4 325 reviews
Siesta Key, FL
02/07 – 05/07
NZ$1708/nighttotal: NZ$5124 (3 )

Walk To Siesta Key Beach & Village | Private Patio | Prime Location!

1 2
apartment, Siesta Key
This family-friendly apartment is located in Siesta Key, within 3km of Siesta Key Beach, Irma Beach, and St. Boniface Episcopal Church Labyrinth, offering easy access to popular destinations. It has excellent ratings for location, cleanliness, and user experience.
The apartment has one bedroom and one bathroom, accommodating up to two guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a garden, and free parking.
Midnight Cove Ii 831f - Beautiful Siesta Key Vacation Rental! - Siesta Key, FL
9.0 2 reviews
Siesta Key, FL
18/07 – 25/07
NZ$423/nighttotal: NZ$2961 (7 )

Midnight Cove Ii 831f - Beautiful Siesta Key Vacation Rental!

2 2
apartment, Siesta Key
This Siesta Key beachfront condo is situated a short 1.6km walk from Crescent Beach and Siesta Key Beach, and under 1.6km from Siesta Key Marina and Point of Rocks.
The 84 square metre apartment sleeps four guests in two bedrooms and two bathrooms, boasting a fully equipped kitchen, swimming pool, spa, fitness centre, tennis court, and parking, plus convenient access to an on-site water park and barbecue grills.
Our House At The Beach C-220 Perfect Getaway! - Siesta Key, FL
9.6 7 reviews
Siesta Key, FL
10/07 – 14/07
NZ$730/nighttotal: NZ$2920 (4 )

Our House At The Beach C-220 Perfect Getaway!

2 6
apartment, Siesta Key
This two-bedroom house is located on Siesta Key, within 1.6 kilometres of St. Boniface Episcopal Church Labyrinth and Siesta Key Beach, and within 3.2 kilometres of Crescent Beach and Siesta Key Marina, offering a convenient location for exploring the area. The property boasts excellent user ratings, indicating a high level of satisfaction from previous guests.
The 126 square metre house features a comfortable layout with a balcony, a fully equipped kitchen, laundry facilities, and two bathrooms. Guests can enjoy a range of amenities, including a swimming pool, spa, garden, and direct beach access, allowing them to relax and enjoy the Siesta Key lifestyle.
Blue Seas & Sand 2br Beach Club Siesta 200c By Rva - Siesta Key, FL
9.2 62 reviews
Siesta Key, FL
04/08 – 05/08
NZ$852/nightfor 1 night

Blue Seas & Sand 2br Beach Club Siesta 200c By Rva

2 4
apartment, Siesta Key
The Beach Club At Siesta Key #200c Resort By Rva is situated just a mile from Crescent Beach and Siesta Key Beach, offering a peaceful escape from the hustle and bustle of downtown Siesta Key. The property enjoys excellent user ratings for its location, cleanliness, and overall experience.
The two-bedroom apartment can comfortably accommodate up to six guests, providing a spacious and relaxing environment. It boasts a range of amenities including a swimming pool, Jacuzzi, tennis court, and barbecue facilities, ensuring a fun-filled and memorable stay for the whole family.
Luna Nueva: Private Pool, New Renovation, Sleeps 8 - Siesta Key, FL
10 2 reviews
Siesta Key, FL
03/07 – 05/07
NZ$1169/nighttotal: NZ$2338 (2 )

Luna Nueva: Private Pool, New Renovation, Sleeps 8

3 8
apartment, South Sarasota
This South Sarasota villa, situated in the Luna Neuva district, provides a private retreat with convenient access to local attractions, being just 3.5 kilometres from Siesta Key Beach and 8 kilometres from the John and Mable Ringling Museum of Art.
Accommodating up to eight guests across three bedrooms and two bathrooms, this newly renovated apartment boasts a private heated swimming pool, a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, garden, and parking, with the option to combine with the adjacent sister unit, Villa Las Flores, to form Luna Flores.
Lake View Condo - Siesta Key, FL
10 15 reviews
Siesta Key, FL
30/07 – 05/08
NZ$337/nighttotal: NZ$2022 (6 )

Lake View Condo

1 2
apartment, Siesta Key
This Siesta Key apartment is situated minutes from Crescent Beach, offering easy access to nearby restaurants and bars.
The one-bedroom flat sleeps two, features a spacious kitchen and living area, a screened patio, and access to a yard; amenities include air conditioning, parking, and internet access.
[Sunny In Siesta]  King Bed + Walk To Beach - Siesta Key, FL
9.8 13 reviews
Siesta Key, FL
27/06 – 30/06
NZ$457/nighttotal: NZ$1371 (3 )

[Sunny In Siesta] King Bed + Walk To Beach

1 2
apartment, Siesta Key
This Siesta Key apartment offers a superb seaside location, a short 2.4km walk from Crescent Beach and Siesta Key Beach, and 3.4km from Turtle Beach.
The two-bedroom, two-bathroom flat sleeps four guests, features a fully equipped kitchen, private balcony, on-site parking, and is close to bicycle rentals for exploring the island.
Lj's Cottages 3 - Balcony Views Beach Pool Sand Sunsets - Siesta Key, FL
9.2 15 reviews
Siesta Key, FL
04/09 – 08/09
NZ$852/nighttotal: NZ$3408 (4 )

Lj's Cottages 3 - Balcony Views Beach Pool Sand Sunsets

2 8
apartment, Siesta Key
This Siesta Key beachfront apartment is situated less than 1.6km from Crescent Beach and Siesta Key Beach, and around 3.2km from Turtle Beach.
Sleeping eight guests, this three-bedroom, two-bathroom condo offers a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and BBQ facilities, all within a smoke-free environment.
Tiny House Sand Dollar Near Siesta Key - Siesta Key, FL
9.3 79 reviews
Siesta Key, FL
01/07 – 03/07
NZ$391/nighttotal: NZ$782 (2 )

Tiny House Sand Dollar Near Siesta Key

2 3
apartment, Gulf Gate Estates
This two-bedroom house is situated in Gulf Gate Estates, Sarasota, within easy reach of Gulf Gate Mall and just a short drive (around 6.4 km) to Crescent Beach and Siesta Key Beach.
The property offers a comfortable stay for up to four guests, with amenities such as a fully equipped kitchen, a terrace, a garden, parking and internet access.

Best family friendly Siesta Key, FL holiday rentals

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

119 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 2 reviews
Siesta Key, FL
11/07 – 18/07
NZ$523/nighttotal: NZ$3661 (7 )

119 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

2 4
apartment, Siesta Key
This second-floor condominium in the Gulf and Bay Club Bayside is located a short walk from Siesta Key/Crescent Beach, offering a tranquil residential setting.
This 118 square meter apartment sleeps four guests and features two bedrooms and two bathrooms, with amenities including a swimming pool, tennis court, fitness centre, spa, and included beach essentials.
Siesta Key Beach - 2 Bedroom - 3 Beds - 3 Bathroom Duplex With Heated Swimming Pool - Siesta Key, FL
9.2 148 reviews
Siesta Key, FL
25/12 – 02/01
NZ$755/nighttotal: NZ$6040 (8 )

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

2 5
apartment, Siesta Key
This apartment is located just a short walk from Crescent Beach and a short drive from Siesta Key Beach, offering easy access to the island's beautiful beaches and vibrant atmosphere. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has two bedrooms and three bathrooms, providing plenty of space for families or groups of friends. Guests can enjoy a range of amenities, including a heated swimming pool, a private beach, a fully equipped kitchen, a spacious balcony, and free Wi-Fi and parking.
119 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Siesta Key, FL
10 1 review
Siesta Key, FL
06/07 – 13/07
NZ$442/nighttotal: NZ$3094 (7 )

119 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

2 4
apartment, Siesta Key
This two-bedroom flat is located in the Gulf & Bay Club Bayside community on Siesta Key, a mere 500-metre walk from the famous sandy beaches and within easy reach of Siesta Key Village.
This 118 square metre condominium offers accommodation for four, featuring a well-equipped kitchen, air conditioning, Wi-Fi, and access to community amenities including two swimming pools, tennis and pickleball courts, and a fitness centre.
70 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
Siesta Key, FL
25/06 – 01/07
NZ$463/nighttotal: NZ$2778 (6 )

70 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests

2 4
apartment, Siesta Key
This ground-floor condominium on Siesta Key is located on the IntraCoastal waterway, offering views and 5-minute walk to private beach access, centrally positioned between Siesta Key Village and the shops at South Bridge.
This 70 square meter apartment sleeps six, featuring two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a swimming pool, garden, and parking, with beach essentials provided for your convenience.

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

Remodeled Condo/perfect Location - Siesta Key, FL
9.7 55 reviews
Siesta Key, FL
14/07 – 16/07
NZ$451/nighttotal: NZ$902 (2 )

Remodeled Condo/perfect Location

1 2
apartment, Siesta Key
This Siesta Key apartment is situated steps from Crescent Beach and within easy walking distance of local restaurants.
The newly remodelled one-bedroom flat offers a luxurious full kitchen, a heated saline pool, and sleeps four guests in comfort, boasting a Stearns & Foster mattress and Italian leather sleeper sofa.
Your Dreamoasisawaits: Siestakeyescape With Pool! - Siesta Key, FL
10 114 reviews
Siesta Key, FL
04/08 – 05/08
NZ$1139/nightfor 1 night

Your Dreamoasisawaits: Siestakeyescape With Pool!

1 4
apartment, Siesta Key
This Siesta Key holiday home is situated 1.6km from Siesta Key's beaches, offering easy access to the island's attractions.
The two-bedroom, two-bathroom property sleeps six, boasting a private pool, fully equipped kitchen, and open-plan living space with a king-size, queen-size bed and queen-size sofa bed.
Calini Beach Club By Coolvacay - Siesta Key, FL
Siesta Key, FL
04/07 – 08/07
NZ$618/nighttotal: NZ$2472 (4 )

Calini Beach Club By Coolvacay

1 4
apartment, Siesta Key
Holiday rental. You will be based in Siesta Key.
Facilities and services include free parking, a fridge and a pool table. Take advantage of the terrace in this apartment in Siesta Key.
Luxury Waterfront Views - Heated Pool - 1400sf Duplex - Minutes To The Beach - Siesta Key, FL
9.3 85 reviews
Siesta Key, FL
12/07 – 19/07
NZ$558/nighttotal: NZ$3906 (7 )

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

2 5
apartment, Siesta Key
This Siesta Key duplex, a four-minute walk from Crescent Beach and 1.9 kilometres from Siesta Key Beach, offers easy access to Sarasota attractions such as the John and Mable Ringling Museum of Art (17.7 kilometres away) and the Sarasota Opera (12.4 kilometres away).
The 130 square metre property boasts a spacious two-bedroom, three-bathroom layout, a private heated pool, free parking, and on-site tennis facilities, perfect for a relaxing Siesta Key getaway.

Frequently asked questions about holiday rentals in Siesta Key, FL

Destinations nearby

Best Siesta Key, FL holiday rentals with a balcony

Siesta Key 1-bedroom Condo | Unit 102b At The Beach Club  Steps To The Beach - Siesta Key, FL
9.0 1108 reviews
Siesta Key, FL
18/07 – 25/07
NZ$637/nighttotal: NZ$4459 (7 )

Siesta Key 1-bedroom Condo | Unit 102b At The Beach Club Steps To The Beach

2 4
apartment, Siesta Key
The Beach Club At Siesta Key #103e Resort By Rva is situated on Siesta Key, just a short walk from both Crescent Beach and Siesta Key Beach, making it ideal for those seeking a beachside escape. The property enjoys excellent ratings for location, cleanliness and overall user experience.
This two-bedroom apartment offers comfortable accommodation for families or groups of friends. Guests can enjoy a range of amenities including a swimming pool, a jacuzzi, a terrace, a garden, a spa, a restaurant, a tennis court and free parking.
Siesta Key Escape Ground Floor Steps To Heated Pool And Free Trolley - Siesta Key, FL
8.8 82 reviews
Siesta Key, FL
01/11 – 10/11
NZ$504/nighttotal: NZ$4536 (9 )

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

2 2
apartment, Siesta Key
This Siesta Key ground-floor apartment offers immediate access to a heated pool, the free Siesta Key trolley, and is within walking distance of Crescent Beach and Siesta Key Beach, lying approximately 17.7km from the John and Mable Ringling Museum of Art.
The 101 square metre property features a spacious two-bedroom, two-bathroom layout with a living room, equipped kitchen, private terrace with barbecue, and access to a swimming pool, Jacuzzi, tennis court, and on-site billiards; sleeping up to four guests comfortably.
Private Beach, Gulf View From Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout - Siesta Key, FL
9.8 119 reviews
Siesta Key, FL
12/07 – 18/07
NZ$675/nighttotal: NZ$4050 (6 )

Private Beach, Gulf View From Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

1 2
apartment, Siesta Key
This Siesta Sands Beach Resort Gulf View apartment is situated on Siesta Key, just 1.6 kilometres from Crescent Beach and Siesta Key Beach, and within a 24-kilometre drive of Siesta Key Marina and Point of Rocks, offering a peaceful escape from the busier parts of the island. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The one-bedroom apartment is 80 square metres in size and can accommodate up to six guests. It provides a comfortable and independent stay with amenities such as a swimming pool, fitness centre, and direct beach access, as well as Wi-Fi and a Smart TV.
Book Me Baby! Bayview Beauty At Siesta Key - Siesta Key, FL
10 174 reviews
Siesta Key, FL
04/07 – 11/07
NZ$507/nighttotal: NZ$3549 (7 )

Book Me Baby! Bayview Beauty At Siesta Key

2 4
apartment, Siesta Key
This Siesta Key apartment, situated within the Midnight Cove II community, is a 1.6km walk from Siesta Key Beach and close to Siesta Key Village's shops and restaurants.
The 130 square metre, two-bedroom, two-bathroom condo sleeps five, boasting a balcony with bay and waterway views, a fully equipped kitchen, laundry facilities, and access to a pool, spa, and private beach access.

Best Siesta Key, FL holiday rentals with parking

Sarasota Coastal Style Minutes To Siesta Beaches - Siesta Key, FL
Siesta Key, FL
30/07 – 05/08
NZ$319/nighttotal: NZ$1914 (6 )

Sarasota Coastal Style Minutes To Siesta Beaches

2 2
house, Siesta Key
This Sarasota coastal-style house is situated a short distance from Siesta Key's beaches, approximately 9.6km from Sarasota city centre and its attractions including Marina Jack, Sarasota Opera House, and the Sarasota County Visitor Information Centre.
This two-bedroom, two-bathroom property offers 97 square metres of living space, sleeps six guests, and includes free Wi-Fi, air conditioning, parking, and a children's playground; Sarasota Bradenton International Airport is 15km away.
Book Me Baby! Esquina Paraiso On Siesta Key - Siesta Key, FL
10 11 reviews
Siesta Key, FL
12/07 – 19/07
NZ$460/nighttotal: NZ$3220 (7 )

Book Me Baby! Esquina Paraiso On Siesta Key

2 5
apartment, Siesta Key
This Siesta Key Anchorage condo, situated on the fifth floor near the south bridge and a short distance from Siesta Key Village, offers direct beach access across the street.
The 120 square metre (approximately 1292 square feet) apartment boasts three bedrooms, two bathrooms, sleeps six guests, and includes a private terrace, swimming pool access, and resort amenities such as tennis courts and a fitness centre.
Condo #104 Completely Remodeled Siesta Key 2 Bedroom 1 Bath Condo - Siesta Key, FL
8.7 29 reviews
Siesta Key, FL
14/07 – 11/08
NZ$413/nighttotal: NZ$11564 (28 )

Condo #104 Completely Remodeled Siesta Key 2 Bedroom 1 Bath Condo

2 3
apartment, Siesta Key
This Siesta Key apartment is ideally located just 1.6 kilometres from Siesta Key Beach, offering easy access to the famous white sands and turquoise waters, as well as being close to St. Boniface Episcopal Church Labyrinth, Crescent Beach and Siesta Key Marina. The apartment has received very good user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment is spacious, covering 81 square metres and comfortably accommodating up to 6 guests in its two bedrooms and one bathroom. It offers a range of amenities, including a swimming pool, spa, fitness centre, tennis court, and barbecue grills, ensuring a comfortable and enjoyable stay.
[Lounge Like Locals]walk To Siesta Beach +Bikes - Siesta Key, FL
9.8 185 reviews
Siesta Key, FL
14/07 – 16/07
NZ$555/nighttotal: NZ$1110 (2 )

[Lounge Like Locals]walk To Siesta Beach +Bikes

2 2
apartment, Siesta Key
This Siesta Key apartment, less than 0.8km from Siesta Key Village and Beach Access 7, offers easy access to the island's main attractions.
The two-bedroom, one-bathroom dwelling sleeps five, features a private deck, shared laundry facilities, and is equipped with a kitchen including a fridge, freezer, microwave, and dishwasher.
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