Island Estate holiday lettings

We found 890 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Island Estate that are perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as Wi-Fi and parking. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Island Estate

Showing deals for:4 Dec - 11 Dec

Property grounds
Beach
Pool
Exterior detail
Exceptional
(10 reviews)

112 · ☀Pool✔ Kitchen✔ Beach✔ Self Checkin✔ Free Parking✔

Clearwater Beach

7% off
£841
for 7 nights, 1 apartment
£120 per night
includes taxes & fees
112 · ☀Pool✔ Kitchen✔ Beach✔ Self Checkin✔ Free Parking✔
Exterior
Beach
Private kitchen
Living area
Exceptional
(199 reviews)

Newly remodeled Beach House Steps to the Gulf, Private Heated Pool

Clearwater Beach

8% off
£5,277
for 7 nights, 1 home
£754 per night
includes taxes & fees
Newly remodeled Beach House Steps to the Gulf, Private Heated Pool
Sports court
Private Rooftop Terrace with hot tub and views of the beach and bay
Pool
Bunk Room off Master Suite with full over full bunk beds
Exceptional
(200 reviews)

Luxurious, Family Friendly House, Rooftop Terrace, Hot Tub & Breathtaking Views!

Clearwater Beach

8% off
£3,051
for 7 nights, 1 home
£436 per night
includes taxes & fees
Luxurious, Family Friendly House, Rooftop Terrace, Hot Tub & Breathtaking Views!
Tropical gardens, very private Pool, lounging and barbeque back patio/porch
Salvador Dali Museum in nearby St. Pete
Clearwater Marina - Restaurants and many activities
Living/Dining
Exceptional
(178 reviews)

Clearwater Beach Pool House Rental - Just Steps to the Beach

Clearwater Beach

7% off
£3,470
for 7 nights, 1 home
£496 per night
includes taxes & fees
Clearwater Beach Pool House Rental - Just Steps to the Beach
Brand new pickleball courts right across the street
Outdoor spa tub
Living area to socialize and relax
Second bedroom on third level, queen bed
Exceptional
(229 reviews)

Luxury, Family Friendly Townhome - Rooftop Hot Tub Featuring Amazing Beach Views

Clearwater Beach

8% off
£2,538
for 7 nights, 1 home
£363 per night
includes taxes & fees
Luxury, Family Friendly Townhome - Rooftop Hot Tub Featuring Amazing Beach Views
Interior
Indoor/Outdoor living on the water with fire pit
Marina
Living area
Exceptional
(14 reviews)

Largest 4 Bed Townhome on Clearwater Beach, Elevator, Dolphins, Walk everywhere

Clearwater Beach

7% off
£4,956
for 7 nights, 1 home
£708 per night
includes taxes & fees
Largest 4 Bed Townhome on Clearwater Beach, Elevator, Dolphins, Walk everywhere
shared laundry room
Pool
Living area
Kitchen counter
Exceptional
(102 reviews)

Cozy Cottage, 1 minute walk to Beach

Clearwater Beach

8% off
£1,914
for 7 nights, 1 home
£273 per night
includes taxes & fees
Cozy Cottage, 1 minute walk to Beach
Room
Pool
Exterior detail
Terrace/patio
Exceptional
(16 reviews)

102 · ☀Pool✔ Kitchen✔ Beach✔ Self Checkin✔ Free Parking✔

Clearwater Beach

7% off
£834
for 7 nights, 1 apartment
£119 per night
includes taxes & fees
102 · ☀Pool✔ Kitchen✔ Beach✔ Self Checkin✔ Free Parking✔
Interior
Terrace/patio
Private kitchen
Property grounds
Exceptional
(6 reviews)

Brand- new Cozy 2-bedroom cottage with a 2 minute walk to Clearwater Beach

Clearwater Beach

6% off
£1,117
for 7 nights, 1 home
£160 per night
includes taxes & fees
Brand- new Cozy 2-bedroom cottage with a 2 minute walk to Clearwater Beach
Marina
Beach
Living area
Living area
Exceptional
(7 reviews)

Indulge in Waterfront Elegance: Stunning 4/3 Townhome - 2800 Square Feet

Clearwater Beach

7% off
£4,271
for 7 nights, 1 home
£610 per night
includes taxes & fees
Indulge in Waterfront Elegance: Stunning 4/3 Townhome - 2800 Square Feet
Private kitchen
Sunsets galore
View from property
Property grounds
Exceptional
(133 reviews)

Cozy and friendly. All is Well - no damage

Clearwater Beach

7% off
£1,910
for 7 nights, 1 home
£273 per night
includes taxes & fees
Cozy and friendly. All is Well - no damage
Clearwater Beach
Exterior
Interior
Private kitchen
Exceptional
(46 reviews)

New & Luxurious 4/3 Townhouse with boat slip- 2,800 Square Feet

Clearwater Beach

7% off
£4,300
for 7 nights, 1 home
£614 per night
includes taxes & fees
New & Luxurious 4/3 Townhouse with boat slip- 2,800 Square Feet
Patio with Furniture and Grill
Kitchen Area
King Bedroom View1
Laundry Room
Exceptional
(13 reviews)

2-bedroom on Clearwater Beach. One block to the beach.

Clearwater Beach

11% off
£1,161
for 7 nights, 1 home
£166 per night
includes taxes & fees
2-bedroom on Clearwater Beach. One block to the beach.
Living / Dining Room
Exterior
Master BR
Pool
Exceptional
(320 reviews)

Updated condo just steps to the white sand beaches of Clearwater Beach

Clearwater Beach

7% off
£2,112
for 7 nights, 1 apartment
£302 per night
includes taxes & fees
Updated condo just steps to the white sand beaches of Clearwater Beach
Marina
Property grounds
First floor living space with Air hockey, dart board, and XL scrabble board!
 CHEFS DREAM KITCHEN EQUIPPED WITH ALL ESSENTIALS FOR CREATING FABULOUS MEALS!
Exceptional
(30 reviews)

Luxury Waterfront Townhome 3BR w/ Pool, Dock, Boat Slip & 4 Decks, Walk to Beach

Clearwater Beach

5% off
£3,103
for 7 nights, 1 home
£443 per night
includes taxes & fees
Luxury Waterfront Townhome 3BR w/ Pool, Dock, Boat Slip & 4 Decks, Walk to Beach
Terrace/patio
Pool
Exterior detail
Interior
Exceptional
(20 reviews)

142 · Time Travelers Welcome: Your 50s Style Getaway

Clearwater Beach

7% off
£1,264
for 7 nights, 1 apartment
£181 per night
includes taxes & fees
142 · Time Travelers Welcome: Your 50s Style Getaway
Interior
Outdoor dining
Dining
Private kitchen
Exceptional
(5 reviews)

Charming 1-Bedroom Apartment Just Steps From Beautiful Clearwater Beach

Clearwater Beach

8% off
£1,240
for 7 nights, 1 apartment
£177 per night
includes taxes & fees
Charming 1-Bedroom Apartment Just Steps From Beautiful Clearwater Beach
Private kitchen
New Air Conditioning has been installed. Wall unit is obsolete and removed.
Room
The new loveseat is a  recliner
Exceptional
(162 reviews)

Great Studio - Under 2 minute walk to beach where dogs are welcome

Clearwater Beach

8% off
£1,168
for 7 nights, 1 apartment
£167 per night
includes taxes & fees
Great Studio - Under 2 minute walk to beach where dogs are welcome
Living area
Room
Private kitchen
Pool
Exceptional
(8 reviews)

Waterfront 2 Bedroom Retreat w/ Stunning Views • 5-Min Walk to Clearwater Beach

Clearwater Beach

7% off
£1,868
for 7 nights, 1 apartment
£267 per night
includes taxes & fees
Waterfront 2 Bedroom Retreat w/ Stunning Views • 5-Min Walk to Clearwater Beach
Property grounds
Pool
Room
Private kitchen
Exceptional
(8 reviews)

Waterfront 1 Bedroom Retreat w/ Stunning Views • 5-Min Walk to Clearwater Beach

Clearwater Beach

7% off
£1,594
for 7 nights, 1 apartment
£228 per night
includes taxes & fees
Waterfront 1 Bedroom Retreat w/ Stunning Views • 5-Min Walk to Clearwater Beach
Interior
Rooftop view from large table that sits 8.  Views of the city and intracoastal
Gorgeous views from the roof of the intracoastal
You have gorgeous views of the intracoastal from all 4 floors of our home.
Exceptional
(100 reviews)

Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!

Clearwater Beach

7% off
£2,577
for 7 nights, 1 home
£368 per night
includes taxes & fees
Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!
Property grounds
Living area
Waterfront master bedroom with king size bed
Dining
Exceptional
(26 reviews)

Fabulous Waterfront Home. CLEARWATER BEACH. Bayfront. Large private dock

Clearwater Beach

8% off
£4,421
for 7 nights, 1 home
£632 per night
includes taxes & fees
Fabulous Waterfront Home. CLEARWATER BEACH. Bayfront. Large private dock
Outdoor dining
Exterior
Dining
Private kitchen
Very good
(5 reviews)

Family beach stay at the Manatee!

Clearwater Beach

7% off
£1,718
for 7 nights, 1 room
£245 per night
includes taxes & fees
Family beach stay at the Manatee!
Bedroom one
Beach
Property grounds
Living area
Exceptional
(11 reviews)

Tangerine dream newly renovated unit September 2025 with Pool and central AC.

Clearwater Beach

16% off
£1,310
for 7 nights, 1 apartment
£187 per night
includes taxes & fees
Tangerine dream newly renovated unit September 2025 with Pool and central AC.
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Island Estate

  • Stunning Beaches: Island Estate boasts beautiful beaches perfect for sunbathing and swimming, ideal for beach enthusiasts.
  • Outdoor Activities: Families can enjoy a variety of outdoor adventures, from nature reserves to urban parks.
  • Charming Local Culture: Experience the friendly atmosphere and warm locals in the Clearwater area.
  • Dining and Entertainment: Nearby downtown Clearwater offers vibrant dining options for romantic evenings or family outings.
  • Diverse Accommodation: Choose from beachfront condos, private homes, and comfortable apartments for a memorable stay.

Popular types of accommodation around Island Estate

You've chosen Island Estate for your holiday, and now it's time to find the perfect place to stay. Discover the most sought-after accommodation options, including beachfront condos, houses, and comfortable apartments. With a range of Clearwater homes and house rentals, you’re sure to find the ideal holiday rental that meets your needs, providing you with a memorable getaway.

  • Condos: The top choice among visitors to Island Estate, offering modern amenities and stunning views.
  • Houses: A fantastic option for families or groups, providing space and comfort for a home-like experience.
  • Apartments: Ideal for those seeking a self-catering option with convenient access to local attractions.
  • Cottages: Perfect for a quaint getaway, offering charm and a cosy atmosphere.
  • Villas: Luxurious accommodations that provide privacy and upscale amenities for a lavish stay.**

Top attractions near Island Estate

Island Estate in Clearwater Beach, Florida, is perfect for beach lovers and families seeking outdoor adventures. Visitors can explore beautiful beaches, urban parks, and nature reserves that provide a blend of city and natural experiences. Nearby attractions include Clearwater Beach and the mainland, offering a variety of activities to enjoy during your stay. Whether you're looking to relax by the shore or engage in family-friendly outings, Island Estate has something for everyone.

  • Clearwater Beach: A stunning stretch of soft, white sand, Clearwater Beach is perfect for soaking up the sun or enjoying water sports. With vibrant beach vibes, it’s an ideal spot for relaxation and socialising.
  • Sand Key Park: This urban park offers a family-friendly atmosphere with lush greenery and picnic areas. It’s perfect for outdoor activities and enjoying the city's natural beauty, making it a great place for a day out.
  • Beach Walk: A picturesque esplanade that invites romantic strolls and family outings. Lined with palm trees, it offers breathtaking views of the sunset and easy access to the beach.

Things to do recommended for couples

For a romantic getaway at Island Estate, enjoy a fun round at Captain Bligh's Landing mini-golf, unwind with a luxurious experience at Palm Hill Country Club, or indulge in relaxation at Midori Salon and Spa. Each offers a unique atmosphere, perfect for couples.

Things to do recommended for families

Families visiting Island Estate can have a splashing good time at Splash Harbour Water Park, enjoy exciting sports at BayCare Ballpark, and have fun at Celebration Station’s arcade adventures, all within a short drive of the estate.

Things to do recommended for groups

Explore the vibrant Westfield Countryside Mall for shopping, enjoy a round of golf at the Belleview Biltmore Golf Club, or visit the charming Amish Country Store for unique finds, all within a short distance from Island Estate.

What do I need to keep in mind when booking a vacation around Island Estate

If you’re travelling with a group, family, pets, or planning an extended stay, it’s essential to filter your search according to your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Island Estate with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Island Estate with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Island Estate: For many, a family holiday isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Island Estate: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By applying the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Island Estate

Island Estate, nestled in Clearwater Beach, Florida, offers a delightful blend of beachside relaxation and family-friendly adventures. Visitors can explore the charming Clearwater area, known for its warm atmosphere and friendly locals. Nearby, downtown Clearwater provides vibrant dining and entertainment options, making it a perfect spot for romantic evenings or family outings. With its picturesque community and outdoor activities, Island Estate promises an unforgettable holiday experience for all types of travellers.

  • Clearwater Beach: A vibrant coastal city located 373m from Island Estates, Clearwater Beach is renowned for its stunning sandy shores and family-friendly atmosphere. Visitors flock to this beach for its outdoor experiences, with a myriad of water sports and activities available. The area boasts a variety of resorts and a bustling shopping district, complete with shopping malls. Key attractions include the picturesque beach itself, a family-oriented beach area, and nearby theme parks, making it an ideal destination for holidaymakers seeking both relaxation and adventure.
  • Clearwater: Situated 621m from Island Estates, Clearwater is a charming city that offers a delightful blend of beach and outdoor activities. This locale is perfect for families looking to enjoy quality time together, with access to lovely beaches and scenic neighbourhoods. Clearwater features a range of resorts and shopping areas, ensuring that visitors have ample options for both leisure and retail therapy. The prominent beaches and inviting family beach spots are key highlights, making Clearwater a wonderful option for those seeking a laid-back yet engaging holiday experience.
  • Indian Rocks Beach: Located 3.7km from Island Estates, Indian Rocks Beach is a tranquil city known for its inviting atmosphere and picturesque shoreline. This gem attracts families and outdoor enthusiasts alike, with beautiful beaches perfect for swimming, sunbathing, and beachcombing. The area features charming shopping areas and a delightful boardwalk, perfect for leisurely strolls. Visitors can explore the scenic beach and family-friendly neighbourhoods, making Indian Rocks Beach an excellent choice for those looking to unwind while enjoying the natural beauty of Florida’s coastline.

Best time to go to Island Estate

If you're planning a trip to Island Estate, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from February to April, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January61.3°F (16.3°C)Light RainMostly SunnyAverageSlightly Low
February64.6°F (18.1°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March67.8°F (19.9°C)Light RainMostly SunnyModerately HighSlightly High
April73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
May78.3°F (25.7°C)Light RainSunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.3°F (28.5°C)Moderate RainMostly SunnyAverageSlightly High
August83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyModerately LowSlightly Low
October76.6°F (24.8°C)Light RainMostly SunnyModerately LowSlightly Low
November69.6°F (20.9°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December65.5°F (18.6°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you hoping to save some pounds on your next getaway? It might be worth considering a bit of flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new journeys, manage your existing arrangements, or review your reservations. Your saved or booked properties are neatly categorised into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Island Estate?
Prices for holiday rentals in Island Estate vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Island Estate to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Island Estate holiday house rentals?
You can find great discounts on house rentals in Island Estate on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Island Estate holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Island Estate with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Island Estate?
A long-stay holiday rental in Island Estate is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Island Estate for a holiday rental?
The best time to visit Island Estate for a holiday rental is during the peak season from February to April. This period is particularly popular among travellers seeking a warm escape, as the weather is pleasantly mild, with temperatures typically ranging from 18 to 27 degrees Celsius. With the sun shining and vibrant outdoor activities beckoning, it's an ideal time for beach lovers and those eager to explore the stunning coastline.March stands out as the most popular month, drawing visitors who wish to enjoy the lively option and partake in various local events. Whether you're lounging on the beach, indulging in water sports, or enjoying delightful dining experiences, Island Estate offers plenty of opportunities to relax and make lasting memories.For budget-conscious travellers, November presents a fantastic alternative. With fewer tourists around, you can savour the peaceful surroundings while still enjoying the beautiful beaches and charming local attractions. This quieter month allows for a more intimate experience, great for those who prefer a slower pace without compromising on the beauty of the area.Ultimately, your choice of when to visit Island Estate will hinge on whether you're looking for a bustling holiday filled with activities or a tranquil retreat to unwind and explore at your leisure.
How early should I book a Island Estate holiday rental?
Book your Island Estate holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Island Estate, Florida, United States of America?
In Island Estate, Florida, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational activities. The beautiful waterfront offers opportunities for boating and fishing, appealing to those looking to explore the scenic coastline and engage in water sports. The nearby Clearwater Marine Aquarium is a popular destination, where guests can interact with marine life and learn about conservation efforts, making it a great spot for families.Additionally, the picturesque beaches of Clearwater Beach are just a short drive away, providing soft sands and various beachside activities. For those interested in local dining, Island Estate features several charming restaurants along the water, serving fresh seafood and other culinary delights.
Can I change or cancel my Island Estate home rental booking on Vrbo?
To find Island Estate holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Island Estate holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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