Vacation Rentals in Diamond Isle, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  St. Petersburg - Clearwater
  6.  Diamond Isle

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2208 Best Vacation Rentals in Diamond Isle (Starting from $147)

Clearwater Beach Oasis Retreat - Entire Resort
Clearwater Beach Oasis Retreat - Entire Resort
House
Clearwater Beach, FL, USA
0.4k from Diamond Isle center

Air Conditioner, Parking, Security/Safety, Pool, Internet, Child Friendly

10 Bedrooms30 Guests
New to Booking
$2331
Average price / night
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ORANGE BLOSSOM COTTAGE two minute Walk to Beach
ORANGE BLOSSOM COTTAGE two minute Walk to Beach
Cottage
Clearwater, FL, 33767, United States
0.1k from Diamond Isle center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.6

Exceptional

85 reviews

$340
Average price / night
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Coconut Grove Resort Oasis
Coconut Grove Resort Oasis
House
Clearwater Beach, FL, USA
0.4k from Diamond Isle center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

10 Bedrooms30 Guests
New to Booking
$3300
Average price / night
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Beachview 4 bedroom Townhome! 30 second walk from the beach! Free parking!
Beachview 4 bedroom Townhome! 30 second walk from the beach! Free parking!
House
Clearwater, FL, 33767, United States
0.2k from Diamond Isle center

No Smoking

4 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$583
Average price / night
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By the Beach Rentals
By the Beach Rentals
Apartment
Clearwater Beach, FL, USA
0.4k from Diamond Isle center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Self-catering

20 Bedrooms40 Guests
8.9

Fabulous

119 reviews

$1034
Average price / night
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5 Story Townhome, Private Elevator, Hot Tub, Breathtaking Views, Steps to Beach
5 Story Townhome, Private Elevator, Hot Tub, Breathtaking Views, Steps to Beach
House
Clearwater, FL, 33767, United States
0.2k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$615
Average price / night
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Five Palms Suite 102 - Daily - Weekly - Monthly
Five Palms Suite 102 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Kitchen, Pool, Air Conditioner, Balcony/Terrace, Internet, Parking, Wheelchair Accessible

1 Bedroom4 Guests
New to Booking
$252
Average price / night
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Private house in Island Estates, Clearwater Beach
Private house in Island Estates, Clearwater Beach
House
Clearwater, FL, 33767, United States
0.2k from Diamond Isle center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$297
Average price / night
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Five Palms Suite 103 - Daily - Weekly - Monthly
Five Palms Suite 103 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
1.0

Review score

1 reviews

$155
Average price / night
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House for up to 17 guests! 30 second walk to the beach! Pool on the property!
House for up to 17 guests! 30 second walk to the beach! Pool on the property!
House
Clearwater, FL, 33767, United States
0.3k from Diamond Isle center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Patio, Pool, Washer

7 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$1185
Average price / night
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Five Palms Suite 104 - Daily - Weekly - Monthly
Five Palms Suite 104 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
New to Booking
$154
Average price / night
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Waterfront 1 Bedroom Retreat w/ Stunning Views • 5-Min Walk to Clearwater Beach
Waterfront 1 Bedroom Retreat w/ Stunning Views • 5-Min Walk to Clearwater Beach
Apartment
Clearwater, FL, 33767, United States
0.4k from Diamond Isle center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
9.8

Exceptional

8 reviews

$429
Average price / night
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Five Palms Suite 105 - Daily - Weekly - Monthly
Five Palms Suite 105 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

2 Bedrooms9 Guests
New to Booking
$357
Average price / night
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Cozy 1 Bedroom Getaway • Walk to Clearwater Beach
Cozy 1 Bedroom Getaway • Walk to Clearwater Beach
Apartment
Clearwater, FL, 33767, United States
0.4k from Diamond Isle center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom2 Guests
10.0

Exceptional

4 reviews

$430
Average price / night
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Five Palms Suite 106 - Daily - Weekly - Monthly
Five Palms Suite 106 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom6 Guests
10.0

Exceptional

1 reviews

$163
Average price / night
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Five Palms Vacation Rentals- Daily - Weekly - Monthly
Five Palms Vacation Rentals- Daily - Weekly - Monthly
Apartment
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Oceanfront, Air Conditioner, View, Balcony/Terrace, Laundry, Fireplace/Heating, Guest Services

20 Bedrooms87 Guests
8.9

Fabulous

10 reviews

$736
Average price / night
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Clearwater Beach Retreats at Bayside Suite 1
Clearwater Beach Retreats at Bayside Suite 1
Apartment
Clearwater, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$388
Average price / night
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Five Palms Suite 108 - Daily - Weekly - Monthly
Five Palms Suite 108 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
New to Booking
$166
Average price / night
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Clearwater Beach Retreats at Bayside Suite 2
Clearwater Beach Retreats at Bayside Suite 2
Apartment
Clearwater, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$289
Average price / night
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Five Palms Suite 109 - Daily - Weekly - Monthly
Five Palms Suite 109 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Pool, Laundry, Kitchen, Air Conditioner, Balcony/Terrace, Wheelchair Accessible, Parking

1 Bedroom4 Guests
New to Booking
$147
Average price / night
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Clearwater Beach Retreats at Bayside View 3
Clearwater Beach Retreats at Bayside View 3
Apartment
Clearwater, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
7.0

Good

2 reviews

$327
Average price / night
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Coastal Waterside Condo 2 Blocks to Beach
Coastal Waterside Condo 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$312
Average price / night
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Waterfront Coastal Condo 2 Blocks to Beach
Waterfront Coastal Condo 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom4 Guests
New to Booking
$299
Average price / night
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Intracoastal Waterside Studio 2 Blocks to Beach
Intracoastal Waterside Studio 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking

10.0

Exceptional

3 reviews

$306
Average price / night
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Bright Waterfront Studio Walk to Sand
Bright Waterfront Studio Walk to Sand
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking

10.0

Exceptional

1 reviews

$321
Average price / night
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Stylish Waterside Studio 2 blocks to Beach
Stylish Waterside Studio 2 blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking

9.8

Exceptional

6 reviews

$324
Average price / night
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Waterfront Bungalow Oasis 2 Blocks to Beach
Waterfront Bungalow Oasis 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking, Outdoor Space

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$294
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Diamond Isle.

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Frequently Asked Questions

You can explore 2208 verified vacation rentals in Diamond Isle. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Diamond Isle vary depending on the season, property size, and location. Rates typically start from around $147 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Diamond Isle include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Diamond Isle welcome pets. Currently, 30 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Diamond Isle often include amenities such as Balcony/Terrace, Kitchen, and Fireplace/Heating. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.