Holiday Cottages in Siesta Key

Are you in a hurry?

Here is a quick list of hotels in Siesta Key, selected based on their rating

Name of hotel Accommodation Rating Price, $
Sea Club II By Beachside Management

8.0 / 10

(37 Reviews)

From 133$
Crescent Arms Condominiums

9.5 / 10

(8 Reviews)

From 305$
Beachpoint Cottages

9.1 / 10

(263 Reviews)

From 229$
Crescent Street Villas By Beachside Management

7.5 / 10

(26 Reviews)

From 245$
Sun And Sea By Beachside Management

8.9 / 10

(29 Reviews)

From 157$

Siesta Key is a beautiful island located just off of Florida’s Gulf Coast. It is known for its white sand beaches and crystal clear water. There are many choices when it comes to accommodations on Siesta Key, but one option that is often overlooked is Cottage.

Cottage is a small, family-owned and operated business that has been on Siesta Key since 1978. They offer six unique cottages, all of which are just a few steps away from the beach. What makes Cottage so special is that they offer something for everyone. Whether you are looking for a budget-friendly option or something a bit more luxurious, they have you covered.

Another great thing about Cottage is that they are always up for a good time. They offer kayaks, paddle boards, and bicycles for guests to use, and they are always hosting events and activities. From wine tastings to yoga on the beach, there is something for everyone at Cottage.

If you are looking for a unique and affordable option when travelling to Siesta Key, look no further than Cottage.

Siesta Key Accommodation lists:

Table of contents

Classic Siesta Key Beachfront Home Sea Club II By Beachside Management Crescent Arms Condominiums Beachpoint Cottages Holiday Cottages in Siesta Key Crescent Street Villas By Beachside Management Sun And Sea By Beachside Management Sea Club II Cottages By Beachside Management Holiday Cottages in Siesta Key with Private Pool Siesta Key Beach - Tropea 665 #3 Siesta Key Beach 665 #1 Cottage By The Sea By Beachside Management

View all photos

Classic Siesta Key Beachfront Home

📍 552 Beach Road

Classic Siesta Key Beachfront Home lies only 0.8 km from Siesta Key Beach and features entertainment activities, flat - screen TV and a cable flat-screen. This accommodation also comes with a kitchen complete with a fridge and an oven, so you can easily make your favourite dishes.

The property is located within 2 km of the city centre. Crescent Arms is a 10-minute car ride away. The closest beach is 750 metres away. Classic Siesta Key Beachfront Home provides rooms for staying in close to Sarasota Beach.

Check Availability
Add to compare

View all photos

8
Very good
37 Reviews

Sea Club II By Beachside Management

📍 5955 Midnight Pass Road

From 133$

Situated in Siesta Key district, Sea Club II By Beachside Management Villa provides free parking, a golf course and a heated swimming pool at 1.3 km from Siesta Key Beach. The accommodation features air conditioner, a dining area and a sofa in the rooms.

Popular points of interest near the venue include Jamaica Royale and Siesta Harbour Condominium Apt Harbor. It is a 25-minute drive from Sarasota Bradenton International airport and a 10-minute drive to Sarasota Square. The villa is just a 10-minute walk from Siesta Key city centre. You can get to Siesta Key Village in a few minutes by car.

Check Availability
Add to compare

View all photos

9.5
Excellent
8 Reviews

Crescent Arms Condominiums

📍 6312 Midnight Pass Rd. Unit Number 603 S

From 305$

Crescent Arms Condominiums is a beachfront accommodation, located not far from the shaped Crescent Beach. This venue comes with 2 bathrooms, as well as air conditioning, coffee/tea making machines and an iron with ironing board in the rooms.

Crescent Arms is 0.6 km away, while Turtle Beach is 4.2 km from the villa. It is a 20-minute walk from Siesta Key city centre. Spearfish Grill with delectable dishes is 450 metres away. You can get to Sarasota Square in a few minutes by car.

Check Availability
Add to compare

Holiday Cottages in Siesta Key

View all photos

9.1
Excellent
263 Reviews

Beachpoint Cottages

📍 125 Beach Road

From 229$

Beachpoint Cottages is located a 10-minute drive to Sarasota Square and overlooks the garden. It includes rooms with a flat-screen TV with satellite channels, air conditioning and a dining area along with a mini-kitchen with refrigerators and kitchenware.

The property is 20 minutes' walk from the centre of Siesta Key. This venue is situated 600 metres away from Siesta Key Beach Access #5. Serving a variety of dishes, 3.14 Pi Craft Beer & Spirits and Gidget's Coastal Provisions are just 250 metres away. You can get to Jamaica Royale in a few minutes by car.

Check Availability
Add to compare

View all photos

7.5
Very good
26 Reviews

Crescent Street Villas By Beachside Management

📍 1126 Crescent Street

From 245$

Set in Siesta Key district of Siesta Key, Crescent Street Villas By Beachside Management features accommodation with WiFi throughout the venue and a cable flat-screen and a garden. The property offers rooms with air conditioner, a kitchenette and a dining area.

The villa is located only 1.9 km from Escape Room Sarasota. It is about a 5-minute drive from Nontando. American specialities await guests in the nearby Toasted Mango Cafe. You can get to Turtle Beach in a few minutes by car.

Check Availability
Add to compare

Hotels in Siesta Key

Best reviews Hotel ❤️ Classic Siesta Key Beachfront Home
Best mid-range Hotel 🌴 Sea Club II By Beachside Management
Hotel with balcony 🌤️ Crescent Arms Condominiums

View all photos

8.9
Excellent
29 Reviews

Sun And Sea By Beachside Management

📍 1135 Sun And Sea Drive

From 157$

Sun And Sea By Beachside Management Villa features accommodation with free parking, an outdoor swimming pool and a sundeck and is nestled 2.8 km from Siesta Key Beach. Siesta Key Marina is located 450 metres away.

Local attractions include Crescent Arms steps away from the venue and city centre 3 km away. It is 10 minutes’ walk from the beach. A quick bites can offer American and Deli menu and is set 150 metres away. Green Turtle Shell & Gift City is also quite close to this villa.

Check Availability
Add to compare

Holiday Cottages in Siesta Key with Private Pool

View all photos

7.8
Very good
24 Reviews

Sea Club II Cottages By Beachside Management

📍 5955 Midnight Pass Road

From 251$

Located in Siesta Key district, Sea Club II Cottages By Beachside Management features an outdoor pool area, entertainment activities and flat screen TV. The venue is a 10-minute drive from the friendly Edson Keith Estate Park and a 10-minute walk from the centre of Siesta Key.

Popular points of interest near the villa include Jamaica Royale and Siesta Harbour Condominium Apt Harbor. Siesta Beach Pavillion is 16 minutes' walk from the property. The closest beach is 900 metres away. You can get to Lido Key Sandy Beach in a few minutes by car.

Check Availability
Add to compare

View all photos

8.3
Very good
21 Reviews

Siesta Key Beach - Tropea 665 #3

📍 665 Beach Road

From 227$

Situated in Siesta Key district, Siesta Key Beach - Tropea 665 # 4 Venue provides free parking and a spa area at 2.6 km from Edson Keith Estate Park. Climate control, Wi-Fi and a TV are featured in the rooms of this villa.

Popular points of interest near the include Siesta Key Beach and Siesta Key Beach Access 7. Public Beach Access 10 is 500 metres from the property. The centre of Siesta Key is within a 15-minute walk away. You can get to the upscale Saint Armands Circle Outdoor Mall in a few minutes by car.

Check Availability
Add to compare

View all photos

6.8
Good
11 Reviews

Siesta Key Beach 665 #1

📍 665 Beach Road

From 335$

Located in Siesta Key, 2-bedroom Siesta Key Beach 665 # 1 Venue measures 88 m² and can accommodate 6 guests. Sarasota Bradenton International airpot is 20 km from the property, while Siesta Key Beach Access 7 is 0.5 km away.

Local attractions include Siesta Key Beach steps away from the villa and city centre 1 km away. Siesta Key Beach Access 2 is 1.9 km from this venue. It is 10 minutes’ walk from the beach. Siesta Key Beach 665 # 1 Property offers accommodation with direct access to Public Beach Access 10.

Check Availability
Add to compare

Luxury Holiday Cottages in Siesta Key

View all photos

7.2
Good
34 Reviews

Cottage By The Sea By Beachside Management

📍 303 Beach Road

From 134$

Cottage By The Sea By Beachside Management is located in Siesta Key district of Siesta Key and features entertainment activities and flat - screen TV along with an own balcony. Siesta Key Beach is 1.3 km from this venue.

The accommodation is situated 3.1 km from South Lido Park and provides quick access to Public Beach Access 10. It is set within 2 km off the city centre. American cuisine is served at Gilligan's Island Bar and Grill, and Ripfire Pizza and BBQ, which are 350 metres away from the villa. You can get to Siesta Key Drum Circle in a few minutes by car.

Check Availability
Add to compare

View all photos

8.4
Very good
5 Reviews

Wild Lime Cottage

📍 1105 Point Of Rocks Rd

From 309$

Wild Lime Cottage is situated approximately 10 minutes’ drive from Turtle Beach and offers accommodation with complimentary parking, a patio and a heated swimming pool. The 46 m² venue comes with a television with satellite channels, tea and coffee making facilities, and soundproof windows in the rooms.

This villa is set in Siesta Key district and near Green Turtle Shell & Gift City. The centre of Siesta Key can be reached within a 30-minute walk. The friendly Edson Keith Estate Park is 2.5 km away from the property. Siesta Key Marina is set nearby.

Check Availability
Add to compare

View all photos

10
Excellent
1 Reviews

Harbor Towers, 4Th Floor, Modern With Den Villa

📍 5855 Midnight Pass Road #203

From 222$

Harbor Towers Villa is located in a residential area and is within walking distance from Jamaica Royale. This accommodation includes climate control, multi-channel TV and a sitting area.

Siesta Beach Pavillion can be found at a 1 km distance from the venue and Sarasota Square is 4 km away. Siesta Key city centre is a 10-minute walk away. It is 15 minutes’ walk from the beach. You can get to Siesta Key Drum Circle in a few minutes by car.

Check Availability
Add to compare

Dog-Friendly Cottages in Siesta Key

View all photos

8.6
Excellent
21 Reviews

Beautiful Property On Siesta Key

📍 1234 Derby Lane

From 240$

Offering a private pool, a tennis court and a flat screen TV, Beautiful Property On Siesta Key is situated 1.4 km from Siesta Key Beach. Siesta Key Village is 1.5 km from the venue.

Located in Siesta Key district, the accommodation is 1 km from the centre of Siesta Key. This villa is also set close to Siesta Harbour Condominium Apt Harbor. The shaped Crescent Beach is a walking distance from Beautiful Property On Siesta Key.

Check Availability
Add to compare

View all photos

5.9
Good
15 Reviews

A Shore Thing By Beachside Management Villa

📍 603 Beach Road, Fl 34242, Siesta Key, Us

From 392$

A Shore Thing By Beachside Management Villa is located in Siesta Key district and features a garden, flat-screen TV and barbecue. The venue is a 10-minute drive from Sarasota Square and a 15-minute walk from the centre of Siesta Key.

At this accommodation you'll be 0.2 km from Seaside Vacation Villas. It is 15 minutes’ walk from the beach. Big Olaf Creamery, serving American specialities, is accessible within a 15-minute walk. Sarasota Beach is just around the corner.

Check Availability
Add to compare

View all photos

7.1
Good
30 Reviews

Casa Del Miramar By Beachside Management Villa

📍 94 Columbus Blvd

From 159$

Offering entertainment activities and a cable flat-screen, Casa Del Miramar By Beachside Management Villa is situated in Siesta Key district, 2.8 km from South Lido Park. It includes rooms with a patio, coffee/tea making machines and smoke detectors along with a kitchen with refrigerators and glassware.

Siesta Key Beach lies within a 20-minute walk of the venue. The centre of Siesta Key is at 2 km. It is about 300 metres to The Hub Baja Grill where guests can enjoy various meals. You can get to Shell Beach in a few minutes by car.

Check Availability
Add to compare

View all photos

8.9
Excellent
5 Reviews

Dockside Delight By Beachside Management Villa

📍 325 Avenida Madera, 34242, Siesta Key, Us

From 478$

A 25-minute stroll from Dockside Delight By Beachside Management Villa takes guests to Nontando, while Sarasota Beach is a 30-minute walk away. A TV set with satellite channels, a kitchenette and ironing facilities are available at this venue.

Situated in Siesta Key district, the accommodation offers access to the shaped Crescent Beach. The walk to the centre of Siesta Key will last for 10 minutes. The closest beach is 600 metres away. Popular points of interest around the property include Siesta Harbour Condominium Apt Harbor.

Check Availability
Add to compare

View all photos

6.3
Good
26 Reviews

Bay Oaks - 6157 #E01 Villa

📍 6157 Midnight Pass Road

From 150$

Bay Oaks - 6157 # E01 Villa is set in Siesta Key district of Siesta Key and offers accommodation with a kitchen and 2 bedrooms. It also comes with free WiFi in the rooms.

The venue is located a 10-minute ride from Siesta Key Beach Access 7. Grand Canal is around 2.6 km away from the property. The city centre is 2 km away. The proximity to Siesta Harbour Condominium Apt Harbor is a perk for those staying at Bay Oaks - 6157 # E01 Villa.

Check Availability
Add to compare

View all photos

6.2
Good
1 Reviews

Ocean Blue By Beachside Management Villa

📍 113 Beach Road, 34242, Siesta Key, Us

From 986$

Ocean Blue By Beachside Management Villa offers rooms with sea views in proximity of Siesta Key Beach Access 2. This accommodation includes a dining area, ironing facilities and a sofa.

The property is 3.3 km away from Bay Island. It is 5 minutes’ walk from the beach. It is a 20-minute walk from Siesta Key city centre. You can get to Siesta Key Beach in a few minutes by car.

Check Availability
Add to compare

View all photos

8.7
Excellent
9 Reviews

Sea Club II 5955 #8E Villa

📍 5955 Midnight Pass Road

From 263$

Sea Club II 5955 # 8E Venue provides guests with an outdoor pool and an outdoor pool area, and is a 16-minute walk from Siesta Key Beach. Siesta Key Drum Circle is 1.4 km from the accommodation.

Popular points of interest near the villa include Jamaica Royale and Siesta Harbour Condominium Apt Harbor. It is 10 minutes’ walk from the beach. The city centre of Siesta Key is 1 km away. You can get to Siesta Key Marina in a few minutes by car.

Check Availability
Add to compare

View all photos

7.3
Good
7 Reviews

Lookout By Beachside Management

📍 641 Beach Road

From 494$

This The Lookout By Beachside Management Villa is located not far from Siesta Key Beach. The 297 m² venue comes with climate control, coffee/tea making facilities and a dressing area in the rooms.

Seaside Vacation Villas is just 0.4 km away from the villa. Siesta Key Drum Circle is a mere 0.7 km away. The closest beach is 550 metres away. The property is set near Siesta Key Beach Access 7, in Siesta Key district.

Check Availability
Add to compare

View all photos

6
Good
5 Reviews

Buttonwood Cottage

📍 1105 Point Of Rocks Rd

From 429$

Buttonwood Cottage provides accommodation with complimentary parking, an outdoor swimming pool and a sundeck in Siesta Key district of Siesta Key. The friendly Edson Keith Estate Park is 10 minutes' drive and Siesta Beach Pavillion can be reached with a 15-minute drive.

Local attractions include Siesta Key Marina steps away from the venue and city centre 3 km away. It is 15 minutes’ walk from the beach. You can find a range of American dishes at Toasted Mango Cafe set nearby, within a 5-minute walk. You can get to Turtle Beach in a few minutes by car.

Check Availability
Add to compare

View all photos

8.1
Very good
55 Reviews

Siesta Key Bay View Villa

📍 1232 Derby Lane

From 270$

Siesta Key/ Derby Bay Villa provides guests with a nightclub, a patio and a golf course, and is a 10-minute walk from Jamaica Royale. Popular points of interest near the venue include the shaped Crescent Beach and Siesta Harbour Condominium Apt Harbor.

The accommodation is located in Siesta Key district and less than 1 km from the city centre. Siesta Key Beach is nestled 1.4 km from the villa. It is close to a beach. You can get to Sarasota Square in a few minutes by car.

Check Availability
Add to compare

View all photos

9.4
Excellent
5 Reviews

Fanta-Sea On The Beach 53 By Beachside Management

📍 53 Beach Road

From 748$

Fanta-Sea On The Beach 53 By Beachside Management Villa is a beachfront accommodation that is set close to Siesta Key Craft Festival Museum, with views of the sea. The venue provides free shuttle bus service and concierge service.

The villa is set in Siesta Key district, 3.2 km from Bay Island and 2.9 km from Jamaica Royale. An own beach is within 900 metres away. Another Broken Egg Cafe and Jo-To Japanese Restaurant are set 450 metres away from the property. Check out Siesta Key Beach Access 2 which is set close by.

Check Availability
Add to compare

View all photos

7.6
Very good
7 Reviews

A House On Siesta Beach By Beachside Management Villa

📍 99 Beach Road

From 545$

A House On Siesta Beach By Beachside Management Villa is situated in Siesta Key district of Siesta Key and offers a mini club, a wading pool and a playground for guests with children. The accommodation features a TV set, a dining area and an iron/ironing board.

Siesta Key Village lies within a 20-minute walk of the venue. The city centre is 2 km away. Offering a variety of dishes, Made in Rome Organic Gelato and MVP-My Village Pub are just about 350 metres away. A House On Siesta Beach By Beachside Management Villa is set in the vicinity of Siesta Key Beach Access 2.

Check Availability
Add to compare

View all photos

10
Excellent
2 Reviews

Fanta-Sea 47 By Beachside Management

📍 47 Beach Road

From 394$

Fanta-Sea 47 By Beachside Management Villa is situated approximately 5 minutes’ drive from Siesta Key Beach and offers accommodation with complimentary parking, a golf course and a sundeck. Guests can take advantage of free shuttle bus service, concierge service and grocery delivery service as well as free Wi Fi throughout the venue.

Popular points of interest near the villa include Siesta Key Beach Access 2 and Siesta Key Craft Festival Museum. Siesta Beach Pavillion is a 25-minute walk away. Furthermore, the centre of Siesta Key is 20 minutes away from the property. You can get to Lido Key Sandy Beach in a few minutes by car.

Check Availability
Add to compare

View all photos

6.3
Good
9 Reviews

Wild Coffee Villa

📍 1105 Point Of Rocks Rd

From 279$

Wild Coffee Villa is set 3.3 km from Turtle Beach and represents a 1-bedroom venue with a patio. A kitchenette, a dining area and a sofa set as well as a mini-kitchen with coffee/tea making equipment and glassware are featured in this accommodation.

The villa is located a 30-minute walk from the heart of Siesta Key, near Green Turtle Shell & Gift City. Nontando is 5 minutes’ drive away. Serving a wide range of dishes, 7-Eleven and Toasted Mango Cafe are about 300 metres from the property. Popular points of interest close to Wild Coffee Villa include Siesta Key Marina.

Check Availability
Add to compare
Holiday Cottages in Siesta Key FAQ
Which Cottage are popular among city visitors?
These Cottage are known for their convenient locations, and positive customer reviews:
What are the best budget villas in Siesta Key?
We recommend Wild Lime Cottage with an outdoor swimming pool, complimentary private parking and a free car park on site. It's set 3.1 km from Siesta Key Beach and has Anna's II restaurant nearby. Another option is Wild Coffee for 279US$ per night, located 500 metres from Siesta Key Marina.
What is the top cheap villa in Siesta Key with weekly rates?
According to original-cottages.com travel data, the best one is Fanta-Sea On The Beach 55 By Beachside Management with fishing, a free private car park and free parking. It costs 13503US$ per week.

Location