Vacation Rentals in Siesta Key, FL

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Siesta Key, FL holiday rentals
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7731 Holiday rentals and Airbnb in Siesta Key, FL

Explore Our Range of Family-Friendly Holiday Rentals in Siesta Key, FL, United States

Give the kids instant access to beach fun and wide-open spaces to unwind at family holiday rentals in Siesta Key, FL, United States.

Crescent Arms 105n - Siesta Key, FL
9.3 76 reviews

Crescent Arms 105n

house, Siesta Key
Crescent Arms 105N is a beachfront property in Sarasota, just a 2-minute walk from Crescent Beach and 2.6 kilometres from Siesta Key Beach, offering a peaceful escape close to the action. This vacation home has excellent user, location and cleanliness ratings.
The two-bedroom property features a fully equipped kitchen, a private pool and a patio with sea views. Guests can enjoy a barbecue, take advantage of the car rental service and explore the area at their leisure.
2br Beach Club – Heated Pool, Hot Tub & Beach - Siesta Key, FL
No reviews

2br Beach Club – Heated Pool, Hot Tub & Beach

apartment, Siesta Key
This accommodation is situated in Point O'Rocks, a mere 200-metre walk from Crescent Beach and 17.7 kilometres from Sarasota Bradenton International Airport.
This family-friendly flat offers two bedrooms and two bathrooms, sleeping up to 11 guests with 71 square metres of floor area, featuring sea views from its patio and access to a shared heated swimming pool and hot tub.
Gertrude Siesta | Private Patios, Beach & Village, 100 Steps To Best Views On Siesta Key! - Siesta Key, FL
9.7 179 reviews

Gertrude Siesta | Private Patios, Beach & Village, 100 Steps To Best Views On Siesta Key!

apartment, Siesta Key
This family-friendly holiday home is located in Siesta Key, just a mile from Irma Beach and Siesta Key Beach, and within a three-mile radius of Shell Beach and St. Boniface Episcopal Church Labyrinth. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation has three bedrooms and three bathrooms, comfortably accommodating up to ten guests. The house offers a range of amenities including a fully equipped kitchen, a swimming pool, a garden, a tennis court, and a water park, providing ample opportunities for relaxation and entertainment.
Siesta Key Studio Close To Beaches, City, And Airport. - Siesta Key, FL
8.4 16 reviews

Siesta Key Studio Close To Beaches, City, And Airport.

studio, Siesta Key
This studio apartment in Siesta Key offers convenient access to St. Armands Circle and the Mall at University Town Centre, located just a few kilometres away, and is also a short distance from Siesta Key Beach and Crescent Beach.
This pet-friendly accommodation sleeps up to three guests with a twin bed and sofa bed, featuring air conditioning, Wi-Fi, a microwave oven, a garden, and parking, making it ideal for exploring local attractions such as Mote Marine Laboratory & Aquarium.

Popular Holiday Rentals with a Swimming Pool in Siesta Key, FL, United States

Discover holiday rentals with a pool in Siesta Key, FL, United States and make every day a swim day.

The Flamingo's Nest At Sea Club Ii - Siesta Key, FL
9.9 154 reviews

The Flamingo's Nest At Sea Club Ii

apartment, Siesta Key
This Sea Club II condo is situated 2.4 kilometres from Siesta Key Village, offering easy access to its shops, restaurants, and nightlife, and boasts direct intracoastal waterway and beach access.
This two-bedroom, one-bathroom apartment sleeps six, features a private pool overlooking the waterway, a tiki hut, charcoal grills, a fishing pier, and provides beach equipment; it was completely remodelled in 2019.
New Listing! Pool Jacuzzi, 3-min To Beach Bars & Entertainment! - Siesta Key, FL
9.0 11 reviews

New Listing! Pool Jacuzzi, 3-min To Beach Bars & Entertainment!

house, Siesta Key
This Siesta Key holiday home is a one-minute walk from Crescent Beach and a 2km drive from Turtle Beach, offering easy access to Siesta Key's bars and entertainment.
The 84 square metre property boasts two bedrooms, two bathrooms, sleeps 15 guests, and includes a private pool, Jacuzzi, and fully equipped kitchen with dishwasher, plus free Wi-Fi.
Sea Horse One Bedroom Pool Walk To Beach - Siesta Key, FL
9.7 4 reviews

Sea Horse One Bedroom Pool Walk To Beach

apartment, Siesta Key
This Sarasota flat is a 4-minute walk from Crescent Beach and 17.7 kilometres from The John and Mable Ringling Museum of Art.
This studio apartment offers a private pool, complimentary parking, free WiFi, a kitchenette with a microwave and fridge, and a garden, accommodating up to three guests.
Heart Of Siesta Key Village, Walk To Beach, Heated Pool, Comes With Beach Gear! - Siesta Key, FL
9.8 879 reviews

Heart Of Siesta Key Village, Walk To Beach, Heated Pool, Comes With Beach Gear!

apartment, Siesta Key
This charming house is just a five-minute walk from the world-renowned Siesta Key Beach, offering a prime location for exploring the beautiful coastline. It has received excellent ratings for cleanliness, location and user experience.
The downstairs property provides a private and quiet setting, perfect for a peaceful getaway. The fully equipped kitchen, air conditioning, free Wi-Fi, and private parking ensure a comfortable and convenient stay.

Frequently asked questions about holiday rentals in Siesta Key, FL

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Popular Holiday Rentals with a Terrace in Siesta Key, FL, United States

Wake up to sweeping, uninterrupted ocean vistas from your personal holiday rentals with a balcony in Siesta Key, FL, United States.

Condo On Siesta Key/crescent Beach. Steps To Ocean And Many Shops/activities! - Siesta Key, FL
9.8 26 reviews

Condo On Siesta Key/crescent Beach. Steps To Ocean And Many Shops/activities!

apartment, Siesta Key
This two-bedroom apartment is located directly on Crescent Beach, Siesta Key's most popular beach, just to the left of the Stickney Point bridge and within easy reach of restaurants and shops. It has been rated excellent by previous guests and offers a fantastic location for a relaxing beach holiday.
The apartment is 110 square metres in size and comfortably accommodates up to six guests. It comes with a range of amenities, including a heated pool, covered parking, BBQ grills, beach lounges, beach towels, elevators, laundry facilities, and free Wi-Fi.
Our House At The Beach Most See<br>at Siesta Key - Siesta Key, FL
9.5 18 reviews

Our House At The Beach Most See<br>at Siesta Key

apartment, Siesta Key
This Siesta Key holiday home is less than 1.6km from Siesta Key Beach and Siesta Key Beach Playground, and within 3.2km of St Boniface Episcopal Church Labyrinth.
The two-bedroom, two-bathroom property sleeps six, boasting a private pool, tennis court, fully equipped kitchen, free Wi-Fi, and sun loungers with beach towels provided.
Villa 6 Walk To Beach 2 Bedroom 2 Bath Pool - Siesta Key, FL
10 1 review

Villa 6 Walk To Beach 2 Bedroom 2 Bath Pool

apartment, Siesta Key
This ground-floor flat in the Point O'Rocks district of Siesta Key offers direct access to Crescent Beach, located approximately 17.7 kilometres from Marina Jack and Sarasota Opera.
This 74 square metre apartment accommodates up to seven guests across two bedrooms and two bathrooms, featuring a private terrace, patio, barbecue facilities, and access to a communal swimming pool and on-site laundry service.
Luxury Private Condo On The Anchorage, Siesta Key Condo 1024 - Siesta Key, FL
9.5 104 reviews

Luxury Private Condo On The Anchorage, Siesta Key Condo 1024

apartment, Siesta Key
This charming two-bedroom house is conveniently located in Siesta Key, just a short walk from both Siesta Key Marina and Crescent Beach, and a short distance from the famous Siesta Key Beach. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The house comfortably accommodates up to six guests and offers a range of amenities including a fully equipped kitchen, a private swimming pool, a tennis court, and a spa. Guests can enjoy a relaxing stay with access to a garden, a terrace, and a fitness centre, and can explore the island's many attractions, including boat rentals, fishing charters, and dolphin watching tours.

Best Siesta Key, FL holiday rentals with parking

Star Fish 3 Bed 2 Bath Pool Walk To Beach - Siesta Key, FL
10 2 reviews

Star Fish 3 Bed 2 Bath Pool Walk To Beach

apartment, Siesta Key
This Siesta Key flat is located in Sarasota, 640 metres from Crescent Beach and approximately 11 kilometres from Marina Jack Restaurant and Marina.
This 60 square metre apartment accommodates up to eight guests across three bedrooms and two bathrooms, featuring a private outdoor swimming pool, garden, sun terrace, barbecue facilities, complimentary WiFi, and free private parking, with lake views from its patio.
Cozy Siesta Key Dream Inn Rental < 1/2 Mi To Beach - Siesta Key, FL
9.9 64 reviews

Cozy Siesta Key Dream Inn Rental < 1/2 Mi To Beach

apartment, Siesta Key
This Siesta Key studio apartment is situated just 0.16 km from Siesta Key Village, providing easy access to shops, restaurants, and nightlife, and a short walk from the renowned Siesta Key Beach.
The self-catering unit sleeps three guests and features a fully equipped kitchen with dishwasher, a shared heated pool, keyless entry, free Wi-Fi, and on-site laundry facilities.
Private Beach Condo: Ideal For Couple/solo Guests! - Siesta Key, FL
10 1 review

Private Beach Condo: Ideal For Couple/solo Guests!

apartment, Siesta Key
This newly renovated one-bedroom flat offers direct access to Siesta Key's private beach, centrally positioned on the island.
This property for two guests features a heated swimming pool, a private patio, a fully equipped kitchen, smart TV with Wi-Fi, and on-site laundry facilities, with a minimum one-month rental period.
Star Fish. 3 Bed 2 Bath. Pool. Daily Rentals - Siesta Key, FL
9.6 270 reviews

Star Fish. 3 Bed 2 Bath. Pool. Daily Rentals

apartment, Siesta Key
This waterfront property is located in Siesta Key, just a 1.6 kilometre walk from Siesta Key Marina and Crescent Beach, and within 5 kilometres of Siesta Key Beach and Turtle Beach. The house has received excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom, two-bathroom home sleeps six guests and offers a fully equipped kitchen, washing machine, TV, and air conditioning. Enjoy the outdoors with a patio, barbecue grills, a swimming pool, a spa, and direct access to the water.

Guest-Favourite High-End Rentals in Siesta Key, FL, United States

Live the ultimate island dream with upscale seaside architecture and absolute privacy at luxury holiday rentals in Siesta Key, FL, United States.

A+ Location Clean 2 Br Condo W Pool Arcade Pets Ok - Siesta Key, FL
9.4 15 reviews

A+ Location Clean 2 Br Condo W Pool Arcade Pets Ok

apartment, Siesta Key

Popular Holiday Rentals in the CBD of Siesta Key, FL, United States

Find holiday rentals in the heart of Siesta Key, FL, United States close to shops and beaches.

Siesta Key Beach - Tropea 665 #3 - Siesta Key, FL
9.4 270 reviews

Siesta Key Beach - Tropea 665 #3

house, Siesta Key
Jamaica Royale - 49 - Siesta Key, FL
9.4 292 reviews

Jamaica Royale - 49

house, Siesta Key
Siesta Key Cottage  Best Value! Just Cross The Street To The Gulf! - Siesta Key, FL
9.3 173 reviews

Siesta Key Cottage Best Value! Just Cross The Street To The Gulf!

apartment, Siesta Key
Cozy 1br Beach Condo On Siesta Key! - Siesta Key, FL
9.7 279 reviews

Cozy 1br Beach Condo On Siesta Key!

apartment, Siesta Key

Popular Holiday Rentals by the Sea in Siesta Key, FL, United States

Open your glass doors and step directly from your living space onto the warm, powdery sand at seashore holiday rentals in Siesta Key, FL, United States.

Minorga On The Gulf - Siesta Key, FL
9.5 37 reviews

Minorga On The Gulf

house, Siesta Key
Villa Fiesta - 312 - Siesta Key, FL
10 1 review

Villa Fiesta - 312

house, Siesta Key
One Ocean - B 1103 - Siesta Key, FL
9.1 388 reviews

One Ocean - B 1103

house, Siesta Key
Perfect 2 Bedroom Apartment On The Anchorage, Siesta Key Apartment 1020 - Siesta Key, FL
9.3 47 reviews

Perfect 2 Bedroom Apartment On The Anchorage, Siesta Key Apartment 1020

apartment, Siesta Key

Best-Rated Holiday Rentals with a Jacuzzi in Siesta Key, FL, United States

Check out holiday rentals with a hot tub in Siesta Key, FL, United States for beachside indulgence.

Coastal Cottage: Renovation Sleep 6 Hot Tub, Pool - Siesta Key, FL
10 42 reviews

Coastal Cottage: Renovation Sleep 6 Hot Tub, Pool

apartment, South Sarasota
Siesta Key Beach Resort And Suites - Siesta Key, FL
8.9 1762 reviews

Siesta Key Beach Resort And Suites

house, Siesta Key
Turtle Beach Resort - Siesta Key, FL
8.8 588 reviews

Turtle Beach Resort

resort, Vamo
2-bedroom, 2 Bathroom Gulf Side #159 Siesta Key  Steps From Siesta Key Beach - Siesta Key, FL
9.8 8 reviews

2-bedroom, 2 Bathroom Gulf Side #159 Siesta Key Steps From Siesta Key Beach

apartment, Siesta Key
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