Search All Cottages in Siesta Key, FL

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Siesta Key, FL cottages
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71 Cottages at the best price in Siesta Key, FL

Handpicked Cottages for Families in Siesta Key, FL

Family-friendly cottages in Siesta Key, FL offer ample room and easy beach access for the whole group.

62 M² Cottage ∙ 1 Bedroom ∙ 4 Guests - Siesta Key, FL
10 3 reviews
Siesta Key, FL
04/07 – 07/07
£490/nighttotal: £1470 (3 )

62 M² Cottage ∙ 1 Bedroom ∙ 4 Guests

1 1
cottage , Siesta Key
Palm Shade Cottage is located in the heart of Siesta Key, just 0.16 kilometres from the famous Siesta Key Beach and a short walk from Siesta Key Village.
The one-bedroom cottage, covering 62 square metres, comfortably sleeps four guests and offers access to a shared heated pool, BBQ area, and a private patio.
63 M² Cottage ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
Siesta Key, FL
24/06 – 01/07
£202/nighttotal: £1414 (7 )

63 M² Cottage ∙ 2 Bedrooms ∙ 6 Guests

2 6
cottage , Sarasota
This Lido Beach holiday home offers direct access to Lido Beach and Lido Pool, with the Bay Runner trolley providing convenient transport to St. Armands Circle's shops and restaurants, located 1.2 kilometres away.
This 63 square metre cottage sleeps up to six guests, featuring two bedrooms, one bathroom, a well-equipped kitchen, air conditioning, a swimming pool, and a garden, with parking and internet also provided.
Drift Inn B, Heated Pool, Beach And Amenities, 2-3 Min Walk - Siesta Key, FL
9.6 533 reviews
Siesta Key, FL
12/09 – 19/09
£161/nighttotal: £1127 (7 )

Drift Inn B, Heated Pool, Beach And Amenities, 2-3 Min Walk

2 3
house , Siesta Key
This charming cottage is a short walk from the soft white sands of Crescent Beach and Siesta Key Beach, making it the perfect base for exploring this popular Florida destination. It has received excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The cottage offers 57 square metres of space, comfortably accommodating up to 4 guests in its two bedrooms. Enjoy the Florida sunshine with a private pool, relax in the garden, and prepare meals in the fully equipped kitchen, complete with a dishwasher, fridge, microwave, and oven.
Charming Coastal Oasis 2bed/2 Bath Cottage Close To Beach And Downtown-southgate - Siesta Key, FL
9.8 80 reviews
Siesta Key, FL
27/07 – 29/07
£326/nighttotal: £652 (2 )

Charming Coastal Oasis 2bed/2 Bath Cottage Close To Beach And Downtown-southgate

3 4
cottage , Southgate
This charming cottage is conveniently located in Southgate, just a short distance from Coconuts Family Entertainment Center, Sarasota Memorial Hospital, and Bee Ridge Park. The surrounding area offers a peaceful escape from the hustle and bustle of the city, with plenty of opportunities for relaxation and exploration. The cottage has consistently received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
The cottage features two bedrooms, accommodating up to six guests, making it ideal for families or groups of friends. Amenities include a private pool, a spa tub, a fully equipped kitchen, and a terrace or balcony, ensuring a comfortable and enjoyable stay.

Best Siesta Key, FL cottages with a garden

5 Min Walk To Beach & Village, Private Pool,on The Canal - Siesta Key, FL
9.8 29 reviews
Siesta Key, FL
31/10 – 07/11
£330/nighttotal: £2310 (7 )

5 Min Walk To Beach & Village, Private Pool,on The Canal

4 4
cottage , Siesta Key
This Siesta Key waterfront holiday home is located within 2km of Siesta Key Beach and Playground, and also close to the Siesta Key Farmers Market and St Boniface Episcopal Church Labyrinth.
This three-bedroom, two-bathroom property boasts 119 square metres of living space, sleeping up to eight guests and offering a private pool, terrace, garden, free Wi-Fi, and parking.
'Vintage Mermaid Cottage' 4 Mi To Siesta Key Beach - Siesta Key, FL
Siesta Key, FL
01/08 – 09/08
£115/nighttotal: £920 (8 )

'Vintage Mermaid Cottage' 4 Mi To Siesta Key Beach

2 2
cottage , Sarasota
This Sarasota detached house is situated approximately 4.8 kilometres from Downtown Sarasota and within easy reach of Siesta Key Beach and Lido Key Beach, as well as cultural sites such as Mote Marine Laboratory and The John & Mable Ringling Museum of Art.
This detached house offers 99 square metres of living space, accommodating up to six guests across two bedrooms and two bathrooms, and features a fully equipped kitchen, free WiFi, and outdoor seating areas.
Lulu's Crescent Cottage #1 - Siesta Key, FL
Siesta Key, FL
21/11 – 01/12
£321/nighttotal: £3210 (10 )

Lulu's Crescent Cottage #1

1 2
cottage , Siesta Key
Lulu's Crescent Cottage #1 is located in Siesta Key, a short distance from the famous Crescent Beach and Siesta Key Beach, as well as the shops and restaurants of Gulf Gate Mall. The surrounding area is quiet and peaceful, offering a welcome retreat from the hustle and bustle of the town centre.
This cosy cottage is ideal for couples, providing a comfortable space to relax and unwind. Amenities include a fully equipped kitchen, air conditioning, a private garden, and a barbecue area, ensuring a relaxing and enjoyable stay.
Lil John Coastal Cottage Near Siesta Key Beach - Siesta Key, FL
9.6 4 reviews
Siesta Key, FL
09/07 – 11/07
£210/nighttotal: £420 (2 )

Lil John Coastal Cottage Near Siesta Key Beach

1 4
cottage , South Sarasota
Lil John Coastal Cottage is situated in South Sarasota, Florida, a short walk from local amenities and a 6.4km drive from Siesta Key Beach.
This two-bedroom, one-bathroom self-catering property sleeps four, boasting a screened porch, fire pit, fully equipped kitchen, and provision of beach chairs, umbrella, and cooler for guests' convenience.

Frequently asked questions about cottages in Siesta Key, FL

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Browse Cottages with a Hot Tub in Siesta Key, FL

Relaxing in a private hot tub after a day at the seaside makes a cottage stay in Siesta Key, FL unforgettable.

Pink Mango Cottage Steps From The Beach - Siesta Key, FL
Siesta Key, FL
31/10 – 07/11
£267/nighttotal: £1869 (7 )

Pink Mango Cottage Steps From The Beach

2 4
cottage , Siesta Key
This Key West-style holiday home is situated in Siesta Key Village, merely 100 metres from Siesta Key Beach and a short drive from St. Armands Circle.
This 46 square metre bungalow offers two bedrooms accommodating up to four guests, featuring air conditioning, a kitchenette with a microwave, a private porch with a grill, and access to a shared jacuzzi pool.
Yellow Palm Cottage Steps From The Beach - Siesta Key, FL
10 1 review
Siesta Key, FL
12/09 – 19/09
£218/nighttotal: £1526 (7 )

Yellow Palm Cottage Steps From The Beach

2 2
cottage , Siesta Key
This Key West-style holiday home is situated in Siesta Key Village, a mere 100 metres from Siesta Key Beach, and within walking distance of Crescent Beach.
This 46 square metre holiday home offers accommodation for up to four guests in two bedrooms, featuring a kitchenette, air conditioning, a shared jacuzzi pool, and parking, with a check-out time of 10:00 AM.
Cozy Cottage Near Siesta Key Village! - Siesta Key, FL
9.0 2 reviews
Siesta Key, FL
22/08 – 05/09
£299/nighttotal: £4186 (14 )

Cozy Cottage Near Siesta Key Village!

1 3
cottage , Siesta Key
This cottage in Siesta Key is located just 150 metres from Siesta Beach and a short walk from Siesta Key Village.
This 51 square metre holiday home sleeps four guests and features two bedrooms, one bathroom, a private kitchen and living room, with access to a shared swimming pool and hot tub, plus complimentary bicycle rentals and beach equipment.

Find the Best Pet-Friendly Cottages in Siesta Key, FL

Secure a dog-friendly cottage in Siesta Key, FL featuring outdoor washing stations and proximity to the shoreline.

Sea Spray Play | Ultimate Beach Escape, Steps From The Sand & St. Armands Cir - Siesta Key, FL
9.0 87 reviews
Siesta Key, FL
22/06 – 29/06
£283/nighttotal: £1981 (7 )

Sea Spray Play | Ultimate Beach Escape, Steps From The Sand & St. Armands Cir

2 6
cottage , Sarasota
This newly renovated cottage in Lido Key offers direct access to Lido Beach's sands and Lido Pool, with St. Armands Circle's boutiques and dining a short open-air Bay Runner trolley ride away.
This pet-friendly property spans 63 square meters, featuring two bedrooms, one bathroom, and accommodation for up to six guests, complete with a well-equipped kitchen, a smart TV, and provided beach equipment for effortless days out.
Lulu's Crescent Cottage #2 - Siesta Key, FL
Siesta Key, FL
24/10 – 03/11
£265/nighttotal: £2650 (10 )

Lulu's Crescent Cottage #2

1 2
cottage , Siesta Key
Lulu's Crescent Cottage #2 is located on Siesta Key, just six kilometres from the town centre, close to both Crescent Beach and Siesta Key Beach, and a short walk from Gulf Gate Mall. The cottage is a peaceful retreat, ideal for couples seeking a quiet escape.
The cottage has one bathroom and can accommodate up to two guests. It includes a fully equipped kitchen, a garden, and free parking, as well as air conditioning, internet access, and a barbecue area.
Beautiful 2 Bed/2 Bath Cozy Cottage Retreat  Your Home Away From Home - Siesta Key, FL
Siesta Key, FL
14/07 – 11/08
£153/nighttotal: £4284 (28 )

Beautiful 2 Bed/2 Bath Cozy Cottage Retreat Your Home Away From Home

2 3
cottage , Sarasota
This detached house is located in the Indian Beach Sapphire Shores district of Sarasota, offering convenient access to Sarasota Airport (800 metres away), Lido Beach, Siesta Key Beach, major hospitals, universities, and the city centre.
This 111 square metre property accommodates up to six guests with two bedrooms and two bathrooms, featuring two living areas, a private fenced garden, and private parking, with pets and internet access permitted.
Charming Beach Bungalow With Private Pool And Steps Away From The Beach! - Siesta Key, FL
10 150 reviews
Siesta Key, FL
27/07 – 29/07
£618/nighttotal: £1236 (2 )

Charming Beach Bungalow With Private Pool And Steps Away From The Beach!

2 4
cottage , Sarasota
This pet-friendly holiday home in Sarasota offers a strategic waterfront position, just a 13-minute walk from the boutiques and eateries of St. Armands Circle and close to Lido Beach for watersports.
Guests can enjoy a well-equipped kitchen with a microwave and dishwasher, air conditioning, a swimming pool, spa, and on-site barbecue, with Wi-Fi, a TV, washer, dryer, linens, and towels provided.

Top-Rated Coastal Cottages in Siesta Key, FL

Book a refreshing coastal escape at comfortable seaside cottages in Siesta Key, FL near the shore.

Walkable To Downtown And Parks Brand New Furniture - Siesta Key, FL
10 1 review
Siesta Key, FL
14/07 – 11/08
£94/nighttotal: £2632 (28 )

Walkable To Downtown And Parks Brand New Furniture

2 3
cottage , Sarasota

Choose the Right Luxury Cottages in Siesta Key, FL

Discover coastal elegance at a luxury cottage near the water in Siesta Key, FL, where quality is paramount.

Chic Peaceful 3bd Cottage - Walk To Siesta! - Siesta Key, FL
10 1 review
Siesta Key, FL
14/07 – 11/08
£104/nighttotal: £2912 (28 )

Chic Peaceful 3bd Cottage - Walk To Siesta!

2 3
cottage , Siesta Key

Check Out Cottages with a Pool in Siesta Key, FL

A cottage in Siesta Key, FL with a pool offers a heated dip right alongside the beach.

Sea Spray Play | Ultimate Beach Escape, Steps From The Sand & St. Armands Cir - Siesta Key, FL
9.0 87 reviews
Siesta Key, FL
22/06 – 29/06
£283/nighttotal: £1981 (7 )

Sea Spray Play | Ultimate Beach Escape, Steps From The Sand & St. Armands Cir

2 6
cottage , Sarasota

Popular Cottages with Parking in Siesta Key, FL

Forget parking stress; every coastal cottage in Siesta Key, FL provides free on-site spaces for your convenience.

Walkable To Downtown And Parks Brand New Furniture - Siesta Key, FL
10 1 review
Siesta Key, FL
14/07 – 11/08
£94/nighttotal: £2632 (28 )

Walkable To Downtown And Parks Brand New Furniture

2 3
cottage , Sarasota

Search Holiday Cottages with Spa Facilities in Siesta Key, FL

Prioritise your well-being with exclusive spa facilities at these waterside cottages in Siesta Key, FL.

Chic Cottage, Vamo Area, Close To Beaches, Pet Friendly, Kayaks, Large Backyard - Siesta Key, FL
9.8 27 reviews
Siesta Key, FL
14/07 – 11/08
£99/nighttotal: £2772 (28 )

Chic Cottage, Vamo Area, Close To Beaches, Pet Friendly, Kayaks, Large Backyard

2 3
cottage , Vamo
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