Siesta Key Luxury Cottages

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

Name of hotel Accommodation Rating Price, $
Siesta Key Beach House

8.0 / 10

(66 Reviews)

From 237$
Crescent Arms Condominiums

9.2 / 10

(11 Reviews)

From 240$
A Shore Thing By Beachside Management Villa

5.9 / 10

(15 Reviews)

From 392$
Casa Del Miramar By Beachside Management Villa

7.1 / 10

(30 Reviews)

From 159$
Fiddle Fig Cottage

7.0 / 10

(4 Reviews)

From 309$

Siesta Key, located in the United States, boasts a collection of exquisite luxury cottages that redefine the essence of opulence and comfort. These upscale accommodations offer a blend of sophistication and tranquility, making them the ideal choice for discerning travelers seeking a lavish escape. From stunning beachfront retreats to secluded hideaways, Siesta Key's luxury cottages cater to every desire and whim, ensuring an unforgettable stay in this tropical paradise.

Siesta Key Accommodation lists:

Table of contents

Siesta Key Beach House Crescent Arms Condominiums A Shore Thing By Beachside Management Villa Classic Siesta Key Beachfront Home Coastal Chic Retreats Casa Del Miramar By Beachside Management Villa Fiddle Fig Cottage Sea Club II By Beachside Management Modern Oasis Escapes Wild Lime Cottage Beach Front And Walking Distance To Village Ocean Blue By Beachside Management Villa

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8
Very good
66 Reviews

Siesta Key Beach House

📍 1232 Derby Lane

From 237$

This 3-bedroom Siesta Key/ Derby Bay Villa is located within 1.4 km from Siesta Key Beach and offers quick access to the shaped Crescent Beach. Guests can take advantage of laundry service and babysitting as well as Wi-Fi throughout the property.

Situated in Siesta Key district, Siesta Key/ Derby Bay Villa right next to Siesta Harbour Condominium Apt Harbor and 10 minutes' ride away from Sarasota Square. You can also walk to Grand Canal, which is about 25 minutes away. This property is set 1 km from the centre of Siesta Key. Sarasota Bradenton International airport lies within 25 km away from Siesta Key/ Derby Bay Villa.

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9.2
Excellent
11 Reviews

Crescent Arms Condominiums

📍 6312 Midnight Pass Rd. Unit Number 603 S

From 240$

The 2-bedroom Crescent Arms Condominiums is located in Siesta Key district of Siesta Key and offers beachfront accommodation fitted with a full kitchen with self-catering facilities. Sarasota Beach is around a 10-minute ride from the Siesta Key villa, while Jamaica Royale is just 1.7 km away.

The centre of Siesta Key can be reached within a 20-minute walk. Dessert restaurant The Orange Octopus is open nearby. The property is located near Crescent Arms. Sarasota Bradenton International airport is the nearest one and it is 20 km from Crescent Arms Condominiums.

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Popular Luxury cottages destinations

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5.9
Good
15 Reviews

A Shore Thing By Beachside Management Villa

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

From 392$

This 7-room A Shore Thing By Beachside Management Villa is located within 10 minutes' walk from Siesta Key Beach and 4.4 km from Sarasota Square. Offering a free car park, a golf course and a private beach area, the villa is set 15 minutes' walk to a beach.

Situated in Siesta Key district, the property right next to Seaside Vacation Villas and approximately a 25-minute walk of the shaped Crescent Beach. This villa is 2 km from the centre of Siesta Key. Guests can dine in the dessert restaurant Big Olaf Creamery located 15 minutes' walk away. The nearest airport is Sarasota Bradenton International, 20 km from A Shore Thing By Beachside Management Villa.

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Coastal Chic Retreats

In Siesta Key, indulge in the epitome of coastal luxury with these chic cottages that exude elegance and style. From tastefully decorated interiors to breathtaking ocean views, these properties offer a seamless blend of comfort and sophistication, making them the perfect sanctuary for those seeking a refined beachside getaway.

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Classic Siesta Key Beachfront Home

📍 552 Beach Road

The shaped Crescent Beach is 25 minutes by foot from Classic Siesta Key Beachfront Home, while Siesta Key Beach is just 0.8 km of here. The accommodation also comes with a kitchen, which is equipped with fridges and an oven.

The villa is a property in Siesta Key, not far from Siesta Key Beach Access 7. This Siesta Key villa is located 5 minutes' walk from the beach. Furthermore, the centre of Siesta Key is 15 minutes away from the accommodation. Classic Siesta Key Beachfront Home is set 2.9 km from Crescent Arms. The nearest airport is Sarasota Bradenton International, around 20 km away.

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7.1
Good
30 Reviews

Casa Del Miramar By Beachside Management Villa

📍 94 Columbus Blvd

From 159$

Casa Del Miramar By Beachside Management Villa is within 4.1 km from Lido Key Sandy Beach, and Siesta Key Beach is about a 20-minute stroll away.

Casa Del Miramar By Beachside Management Villa is located in Siesta Key district of Siesta Key, 24 minutes' drive from Sarasota Bradenton International airport. This property is 2 km from the heart of Siesta Key. Meals or drinks can be enjoyed at Restaurant Bonjour French Cafe, Ripfire Pizza and BBQ placed near the Siesta Key villa. The accommodation is set 1.8 km to Siesta Key Drum Circle.

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Hotels in Siesta Key

Airport nearby ✈️ Lakeland Linder Regional, Charlotte County, St. Pete-Clearwater International, Sarasota Bradenton International, Tampa International
Average Price 💰 502$
Hotels in Siesta Key 🏨 399
Hotel Reviews ⭐ 229
Landmarks nearby 📍 Siesta Key, The Gallery on Siesta Key, Ted Sperling Park, St. Boniface Episcopal Church Labyrinth, Christopher Wheeler Park
Family Hotel 👪 Siesta Key Beach House
Best reviews Hotel ❤️ Crescent Arms Condominiums
Hotel with a view 🔍 A Shore Thing By Beachside Management Villa

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7
Good
4 Reviews

Fiddle Fig Cottage

📍 1105 Point Of Rocks Rd.

From 309$

Set in a 10-minute ride from Turtle Beach and nearly a 20-minute stroll of the shaped Crescent Beach, the 1-bedroom Fiddle Fig Cottage is located in Siesta Key. The accommodation features an equipped kitchen with a microwave, a fridge and kitchenware to meet all guests' needs.

Situated in Siesta Key district, the villa right next to Green Turtle Shell & Gift City and 3.1 km of Siesta Key Beach. This 1-bathroom villa is set 3 km from the centre of Siesta Key. You can find a range of American dishes at Toasted Mango Cafe set nearby, within 300 metres away. Fiddle Fig Cottage is nestled just steps away from Siesta Key Marina. Sarasota Bradenton International airport is within 20 km.

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Modern Oasis Escapes

Escape to a world of modern luxury with these sleek and sophisticated cottages in Siesta Key. Featuring state-of-the-art amenities and contemporary design elements, these properties provide a stylish retreat for travelers looking for a cutting-edge accommodation experience. Unwind in style and comfort amidst the tropical allure of Siesta Key's modern oasis escapes.

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5.9
Good
32 Reviews

Sea Club II By Beachside Management

📍 5955 Midnight Pass Road

From 171$

Sea Club II By Beachside Management Villa offers accommodation in Siesta Key, a 10-minute drive away from Sarasota Square and a 16-minute walk of Siesta Key Beach. This Siesta Key villa has an outdoor swimming pool, a sunbathing terrace and a picnic area.

Situated in Siesta Key district, the property right next to Siesta Harbour Condominium Apt Harbor and within 1.7 km to the shaped Crescent Beach. An own beach lies 900 metres from the Siesta Key accommodation and Sarasota Bradenton International airport is a 25-minute drive away. It is 1 km from the centre of Siesta Key. Jamaica Royale is a walking distance from Sea Club II By Beachside Management Villa.

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9
Excellent
2 Reviews

Wild Lime Cottage

📍 1105 Point Of Rocks Rd

From 309$

This 1-bedroom Wild Lime Cottage is situated within 10 minutes' drive away from Siesta Key Beach and provides quick access to Green Turtle Shell & Gift City. The property also has a full kitchen with a microwave oven, a fridge and kitchenware.

The villa is located in Siesta Key district, where guests can admire the shaped Crescent Beach within a short walk from Siesta Key Marina. Approximately 10 minutes' ride away there is Turtle Beach. City Pizza Bar & Grill is a pizzeria serving American and Italian dishes. The nearest airport is Sarasota Bradenton International, about 25 minutes' drive from Wild Lime Cottage.

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9
Excellent
3 Reviews

Beach Front And Walking Distance To Village

📍 652 Beach Road

From 567$

While staying at the 3-bedroom Beach Front And Walking Distance To Village, you'll be about 20 minutes' walk from the shaped Crescent Beach and at 400 metres of Public Beach Access 10. The beachfront villa is a 203 m² property in Siesta Key, offering 24-hour reception and grocery delivery service.

Popular points of interest near the accommodation include Siesta Key Beach and Seaside Vacation Villas. The beachfront villa is located within 15 minutes' walk of the centre of Siesta Key. The Siesta Key property is set within 10 minutes' drive away from the friendly Edson Keith Estate Park. Sarasota Bradenton International airport can be reached within a 25-minute drive.

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Tranquil Waterfront Havens

Immerse yourself in serenity and luxury with these tranquil waterfront havens in Siesta Key. Nestled along the shores of crystal-clear waters, these cottages offer a peaceful respite from the hustle and bustle of everyday life. Relax on private docks, soak in panoramic views, and experience the ultimate in waterfront living at these exclusive retreats.

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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 is located 3.3 km to Bay Island and 25 minutes' drive to Sarasota Bradenton International airport.

Ocean Blue By Beachside Management Villa is situated in Siesta Key district, in the vicinity of Siesta Key Beach Access 2. You can reach Big Sarasota Pass 10 minutes by car. For meals, guests can head to Big Olaf Creamery, which is about a 5-minute walk away. You can get to Saint Armands Circle nearly a 15-minute drive away.

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9
Excellent
3 Reviews

Fanta-Sea 55 By Beachside Management

📍 55 Beach Road

From 720$

The beachfront Fanta-Sea On Beach 55 By Beachside Management Villa is within 1.9 km of Siesta Key Village, and at 3.3 km distance from the shaped Crescent Beach. This villa is set in Siesta Key district of Siesta Key and offers accommodation with a fully equipped kitchen and 4 bedrooms.

The property for 10 guests is placed next to Siesta Key Craft Festival Museum. It is 2 km from the centre of Siesta Key. The soup reastaurant Lobster Pot Restaurant is nearly a 5-minute walk away. Fanta-Sea On The Beach 55 By Beachside Management Villa is set close to Siesta Key Beach Access 2. The nearest airport is Sarasota Bradenton International, 20 km from the 4-bathroom villa.

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9.1
Excellent
24 Reviews

Sun And Sea By Beachside Management

📍 1135 Sun And Sea Drive

From 213$

The 2-bedroom Sun And Sea By Beachside Management Villa is within 10 minutes' drive away from Siesta Key Beach, and Crescent Arms is around 10 minutes' walk away. The accommodation also comes with a fully-fitted kitchen complete with a refrigerator, an oven and kitchenware, so you can easily make your favourite dishes.

The villa is a property in Siesta Key, not far from Green Turtle Shell & Gift City. This 1-bathroom villa is about 25 minutes' walk from the centre of Siesta Key. The nearby Captain Curt's Crab & Oyster Bar serves meals of American cuisine. Sun And Sea By Beachside Management Villa is set 4.9 km from Sarasota Square Mall. Sarasota Bradenton International airport is at a distance of 20 km from the Siesta Key property.

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Elegant Bohemian Hideaways

Discover a bohemian-inspired paradise at these elegant hideaways in Siesta Key. Combining whimsical charm with refined elegance, these cottages offer a unique and eclectic retreat for travelers with a penchant for artistic flair. Embrace the laid-back yet luxurious atmosphere of these bohemian hideaways and immerse yourself in a world of creativity and relaxation.

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7.8
Very good
24 Reviews

Sea Club II Cottages By Beachside Management

📍 5955 Midnight Pass Road

From 251$

Situated in Siesta Key district, this 7-room Sea Club II Cottages By Beachside Management right next to Siesta Harbour Condominium Apt Harbor and within 20 minutes' walk from the shaped Crescent Beach. Featuring free self-parking, an outdoor swimming pool and a picnic area, the property is a 25-minute walk of Sarasota Beach.

Siesta Key Beach Access 7 lies within 2 km from the villa. This Siesta Key accommodation is located 900 metres of the beach. The villa is 1 km from the heart of Siesta Key. Sea Club II Cottages By Beachside Management is near Jamaica Royale in Siesta Key. Sarasota Bradenton International airport is a 25-minute drive away.

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8.6
Excellent
9 Reviews

Private Beach House Villa

📍 5950 Midnight Pass Rd. Unit 315

From 412$

Private Beach House Villa is located near Siesta Harbour Condominium Apt Harbor, 1.1 km from Siesta Key Beach.

Escape Room Sarasota lies in a 5-minute drive from Private Beach House Villa. It takes a 10 minutes' walk to get to Siesta Key city centre. The beach is in 850 metres away. Guests can visit Crescent Beach situated not far from this villa. Sarasota Bradenton International airport is 25 minutes' drive away.

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7.2
Good
34 Reviews

Cottage By The Sea By Beachside Management

📍 303 Beach Road

From 134$

Cottage By The Sea offers accommodation in Siesta Key, about a 15-minute walk of Siesta Key Beach and within a 10-minute drive from the shaped Crescent Beach.

Cottage By The Sea is located in Siesta Key district of Siesta Key, 24 minutes' drive from Sarasota Bradenton International airport. The walk to the centre of Siesta Key will last for 15 minutes. Guests can enjoy American and Italian delicacies prepared at 3.14 Pi Craft Beer, at 250 metres from this Siesta Key villa. Sarasota Beach is just around the corner.

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Secluded Forest Retreats

Embark on a journey of tranquility and seclusion at these hidden forest retreats in Siesta Key. Surrounded by lush greenery and towering trees, these cottages offer a peaceful escape from the outside world. Breathe in the fresh air, listen to the sounds of nature, and reconnect with yourself at these secluded and enchanting forest retreats.

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7
Good
4 Reviews

Bay Oaks - 6157 #E01 Villa

📍 6157 Midnight Pass Road

From 242$

Bay Oaks - 6157 #E01 Villa is situated in close proximity to Crescent Beach. This villa is 2.6 km from Siesta Key Beach and consists of 2 bedrooms and a kitchen with fridges and an oven.

The property is set right in Siesta Key district near Siesta Harbour Condominium Apt Harbor. It takes 15 minutes on foot to reach Siesta Key city centre. The specialty food market Crescent Beach Grocery Store is situated just a 13-minute stroll of this Siesta Key accommodation. You can get to Turtle Beach 10 minutes by car. Bay Oaks - 6157 #E01 Villa is about 25 minutes' drive from Sarasota Bradenton International airport.

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9.5
Excellent
23 Reviews

Crescent Beach Villas By Beachside Management

📍 1126 Crescent Street

From 253$

Crescent Street Villas By Beachside Management is located 3.1 km from Turtle Beach and 20 km from Sarasota Bradenton International airport. This property has a fully equipped kitchen provided with amenities, such as a microwave, refrigerator and kitchenware for self-catering.

Situated in Siesta Key district, the villa right next to Green Turtle Shell & Gift City and 20 minutes on foot from the shaped Crescent Beach. If you feel like visiting the surroundings, check out Siesta Key Beach about 10 minutes by car. Miguel's Restaurant treats guests with French meals and lies at 450 metres from this Siesta Key accommodation. Crescent Street Villas By Beachside Management is near Siesta Key Marina in Siesta Key. The airport is 25 minutes drive away.

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9.7
Excellent
3 Reviews

Island Time East By Sklrp Villa

📍 355 Calle Miramar Unit East

From 1711$

Island Time East Villa is set in Siesta Key, 15 minutes' walk from Siesta Key Village and 25 minutes on foot from Jamaica Royale.

Located in Siesta Key district, Island Time East Villa offers easy access to Public Beach Access 10. The property is nestled 2 km from the centre of Siesta Key. Dessert restaurant Big Olaf Creamery is open nearby. The villa is set 15 minutes by foot from Siesta Key Drum Circle. Sarasota Bradenton International airport is a 24-minute drive away from Island Time East Villa.

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Harbor Towers, 4Th Floor, Modern With Den Villa

📍 5855 Midnight Pass Road #203

From 252$

The 1-bedroom Harbor Towers Villa offers accommodation for 8 guests in Siesta Key and provides them with a tennis court and a heated pool. At a distance of 1 km, you can visit Siesta Key Beach together with the shaped Crescent Beach located nearby.

Harbor Towers Villa is 600 metres to Jamaica Royale and set in the residential area. The accommodation is about 10 minutes' walk from the centre of Siesta Key. It is 1.1 km to the beach. Harbor Towers Villa is set within 15 minutes' walk to Siesta Key Village. The Siesta Key accommodation awaits guests 26 minutes' drive from Sarasota Bradenton International airport.

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9
Excellent
6 Reviews

Lulu'S Key House Green 1/1 Upstairs

📍 5249 Calle Menorca

From 211$

The 1-bedroom Lulu'S Key House Green 1/1 Upstairs Villa is located in a residential area and is within walking distance from Siesta Key Beach. A kitchen with a microwave, dishwasher and a fridge is included at this Siesta Key villa so that guests can cook for themselves.

The accommodation is set in Siesta Key district, a few steps from Siesta Key Village. Siesta Key Beach Access #10 is set just 0.5 km from the villa. The walk to the centre of Siesta Key will last for 5 minutes. Lulu'S Key House Green 1/1 Upstairs Villa is set in 25 minutes' stroll of Crescent Arms. Sarasota Bradenton International airport is a 24-minute drive from the Siesta Key property.

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9
Excellent
20 Reviews

Siesta Key Beach 665 #1

📍 665 Beach Road

From 330$

This 2-bedroom Siesta Key Beach 665 #1 Villa is set 0.5 km to Siesta Key Beach Access 7 and offers access to Siesta Key Village. While staying in the property, guests are welcome to use a kitchen with a microwave oven and fridges for self-catering.

Situated in Siesta Key district, the villa right next to Seaside Vacation Villas and nearly a 15-minute walk of Grand Canal. The 2-bathroom villa is set 1 km from the centre of Siesta Key. Siesta Key Beach Access 2 is at a 1.9-km distance. Siesta Key Beach 665 #1 Villa offers quick access to Sarasota Bradenton International airport within 26 minutes' drive away.

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Fanta-Sea 53 By Beachside Management

📍 53 Beach Road

From 848$

Crescent Beach is around 10 minutes' drive from this 4-bedroom Fanta-Sea On The Beach 53 By Beachside Management Villa, while Siesta Key Craft Festival Museum is 500 metres of here. The beachfront villa also features a fully-fitted kitchen and amenities such as a fridge, an oven and kitchenware.

Situated 5 minutes' walk of an own beach, the accommodation is located in Siesta Key district of Siesta Key. Situated on the beachfront, this beachfront property is close to Siesta Key Beach Access 2. MVP-My Village Pub can be found about 400 metres away and it serves American dishes. Fanta-Sea On The Beach 53 By Beachside Management Villa is set within 2.9 km to Jamaica Royale. Sarasota Bradenton International airport is 25 minutes’ drive from the Siesta Key property.

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10
Excellent
3 Reviews

Wild Coffee Villa

📍 1105 Point Of Rocks Rd

From 309$

The 1-bedroom Wild Coffee Villa is located in Siesta Key, 3.1 km from Siesta Key Beach as well as 2.5 km of Edson Keith Estate Park. The Siesta Key villa also offers a picnic area, a patio and a sundeck.

Situated in Siesta Key district, the accommodation right next to Green Turtle Shell & Gift City and in 20 minutes' walk from the shaped Crescent Beach. The centre of Siesta Key can be reached within a 30-minute walk. American and Italian meals can be arranged at City Pizza Bar & Grill 300 metres of the Siesta Key property. Siesta Key Marina is set nearby. Wild Coffee Villa is located within a 25-minute drive from Sarasota Bradenton International airport.

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5
Good
2 Reviews

Buttonwood Cottage

📍 1105 Point Of Rocks Rd

From 379$

The 1-bedroom Buttonwood Cottage is set in Siesta Key, 3.1 km of Siesta Key Beach and 20 minutes' walk from Nontando. The facilities of the Siesta Key villa include an outdoor swimming pool, a picnic area and a patio.

The accommodation is located in Siesta Key district, where guests can admire the shaped Crescent Beach within a short walk from Siesta Key Marina. This property is nestled 3 km from the centre of Siesta Key. If you prefer to eat out, Miguel's Restaurant can be found approximately 5 minutes' walk away. Buttonwood Cottage is nestled near Green Turtle Shell & Gift City. The nearest airport is Sarasota Bradenton International located within 20 km from the Siesta Key property.

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6
Good
1 Reviews

Bay Oaks, 4Th Floor Corner - Elevator Hotel

From 125$

The 1-bedroom Bay Oaks, 4Th Floor Corner - Elevator Villa offers accommodation in Siesta Key, within 10 minutes' ride away from Turtle Beach and merely 1.2 km of the shaped Crescent Beach. This Siesta Key villa also features a kitchen and amenities such as a microwave and refrigerator.

The property is located in a residential area of Siesta Key and gives easy access to Crescent Arms. The 2-bathroom villa is set 2 km from the centre of Siesta Key. The nearby Sniki Tiki Bar at Captain Curt's Village serves meals of American cuisine. Popular points of interest around Bay Oaks, 4Th Floor Corner - Elevator Villa include Siesta Harbour Condominium Apt Harbor. Sarasota Bradenton International airport is approximately 25 minutes' drive away.

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8.5
Very good
26 Reviews

Siesta Key Beach - Tropea 665 #3

📍 665 Beach Road

From 482$

This 1-bedroom Siesta Key Beach - Tropea 665 #4 Villa offers accommodation in Siesta Key, 3.3 km to Siesta Key Marina and 20 minutes' walk of the shaped Crescent Beach. The property also comes with a kitchen complete with a microwave oven and a fridge, so you can easily make your favourite dishes.

Situated in Siesta Key district, the villa right next to Seaside Vacation Villas and at 3.6 km distance from Shell Beach. This 1-bathroom villa is set 1 km from the centre of Siesta Key. The closest beach is 0.4 km away. Check out Siesta Key Beach which is set close by. The nearest Sarasota Bradenton International airport is 20 km from Siesta Key Beach - Tropea 665 #4 Villa.

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Siesta Key Luxury Cottages FAQ
Which Luxury cottages have a lot of guest reviews?
Here are some Luxury cottages that have the highest number of reviews:
What are the cheapest villas in Siesta Key?
We recommend Lookout By Beachside Management with a tennis court, an outdoor swimming pool and a picnic area. It's set 0.8 km from Siesta Key Beach Access #10 and costs 692US$ per night. Another perfect option is Siesta Heron Suites & Villas with rating 8.2/10. Located 400 metres from Public Beach Access 10, it offers canoeing, 24 hour front desk assistance and a heated swimming pool.
What is the most popular villa in Siesta Key with weekly rates?
According to 2000floridatravel.com travel data, the best one is Fanta-Sea On The Beach 55 By Beachside Management with the price of 13853US$ per week.
What are the best cottages in Siesta Key offering a pool?
According to 2000floridatravel.com travel data, there are many deals offering a pool.
What are the top family holiday houses in Siesta Key?
Among the best options, we recommend Family Tides By Beachside Management rated 8.0/10 with an outdoor swimming pool, a picnic area and a free private car park on site. It's set in Siesta Key district and costs about 620US$ per night.
Which pet-friendly holiday houses in Siesta Key allow dogs?
If you're searching for a pet-friendly holiday homes, 2000floridatravel.com offers 58 deals to consider. You can book Wild Lime Cottage (rating: 8.8/10) for about 279US$ per night, located 550 metres from Siesta Key Beach Access #5. Another great option is Siesta Key/ Derby Bay at the cost of 320US$ per one night.
What are the top holiday houses in Siesta Key with a hot tub?
If you want to relax and unwind after a long day, 2000floridatravel.com offers 35 deals with hot tubs. Among them, we recommend Avenida Lower rated 8.8/10 with a Jacuzzi, 24-hour front desk and ironing on site. It costs 393US$ per night. Also consider booking Canal Lower-Gorgeous 3 Bed 3 Bath Near Sk Village (rating: 8.4/10) for about 1459US$ per night. It offers a golf course, snorkelling and a Jacuzzi.

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