Entire condo
Caloosa Cove Resort by CoolVacay
Property class: 3
Choose dates to view prices
Photo gallery for Caloosa Cove Resort by CoolVacay





Room options
Check availability for these dates
Available filters for rooms
Showing 30 of 30 rooms
View all photos for Standard Studio, Balcony, Pool View

Standard Studio, Balcony, Pool View
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Queen Bed and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony, Ocean View

Standard Studio, Balcony, Ocean View
- Ocean view
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Queen Bed and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony, Pool View

Standard Studio, Balcony, Pool View
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Double Sofa Bed and 1 Queen Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony

Deluxe Suite, 1 Bedroom, Balcony
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony, Ocean View

Standard Studio, Balcony, Ocean View
- Ocean view
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Double Sofa Bed and 1 Queen Bed
View all photos for Standard Studio, Balcony, Ocean View

Standard Studio, Balcony, Ocean View
- Ocean view
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Double Sofa Bed and 1 Queen Bed
View all photos for Standard Suite, 1 Bedroom, Balcony

Standard Suite, 1 Bedroom, Balcony
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Deluxe Suite, 1 Bedroom, Balcony, Pool View
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony

Deluxe Suite, 1 Bedroom, Balcony
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony

Deluxe Suite, 1 Bedroom, Balcony
- Marina view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony

Standard Studio, Balcony
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Double Sofa Bed and 1 Queen Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony

Deluxe Suite, 1 Bedroom, Balcony
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Suite, 1 Bedroom, Balcony

Standard Suite, 1 Bedroom, Balcony
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed
View all photos for Standard Suite, 1 Bedroom, Balcony, Marina View

Standard Suite, 1 Bedroom, Balcony, Marina View
- Marina view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Marina View

Deluxe Suite, 1 Bedroom, Balcony, Marina View
- Marina view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Deluxe Suite, 1 Bedroom, Balcony, Pool View
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Marina View

Deluxe Suite, 1 Bedroom, Balcony, Marina View
- Marina view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony

Standard Studio, Balcony
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Double Sofa Bed and 1 Queen Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Ocean View

Deluxe Suite, 1 Bedroom, Balcony, Ocean View
- Ocean view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony, Ocean View

Standard Studio, Balcony, Ocean View
- Ocean view
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Double Sofa Bed and 1 Queen Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony

Deluxe Suite, 1 Bedroom, Balcony
- Marina view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Suite, 1 Bedroom, Balcony, Marina View

Standard Suite, 1 Bedroom, Balcony, Marina View
- Marina view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Ocean View

Deluxe Suite, 1 Bedroom, Balcony, Ocean View
- Ocean view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Deluxe Suite, 1 Bedroom, Balcony, Pool View
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony, Ocean View

Standard Studio, Balcony, Ocean View
- Ocean view
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Queen Bed and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Ocean View

Deluxe Suite, 1 Bedroom, Balcony, Ocean View
- Ocean view
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony

Deluxe Suite, 1 Bedroom, Balcony
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Studio, Balcony, Ocean View

Standard Studio, Balcony, Ocean View
- Ocean view
- 400 sq ft
- 1 bedroom
- Sleeps 3
- 1 Queen Bed and 1 Double Sofa Bed
View all photos for Deluxe Suite, 1 Bedroom, Balcony, Pool View

Deluxe Suite, 1 Bedroom, Balcony, Pool View
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 2 Queen Beds and 1 Double Sofa Bed
View all photos for Standard Suite, 1 Bedroom, Balcony, Pool View

Standard Suite, 1 Bedroom, Balcony, Pool View
- 800 sq ft
- 1 bedroom
- Sleeps 6
- 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed
You may also like
Ad

Bayside Inn Key Largo
Key Largo
- On private beach
- Pool
- Pet friendly
- Parking included
8.6 out of 10, Excellent, 1,707 reviews
8.6
Excellent
1,707 reviews
The price is NT$4,896
NT$4,896
NT$6,303 total
includes taxes & fees
May 10 - May 11
Ad

Lime Tree Bay Resort
Long Key
- On private beach
- Pool
- Pet friendly
- Parking included
9.2 out of 10, Wonderful, 1,226 reviews
9.2
Wonderful
1,226 reviews
The price is NT$5,539
NT$5,539
NT$7,663 total
includes taxes & fees
May 3 - May 4
Ad

Fisher Inn Resort & Marina
Islamorada
- On private beach
- Pool
- Breakfast included
- Pet friendly
8.2 out of 10, Very Good, 1,005 reviews
8.2
Very Good
1,005 reviews
The price is NT$4,838
NT$4,838
NT$6,481 total
includes taxes & fees
May 6 - May 7
Ad

Chesapeake Beach Resort
Matecumbe
- On private beach
- Pool
- Breakfast included
- Pet friendly
9.2 out of 10, Wonderful, 1,694 reviews
9.2
Wonderful
1,694 reviews
The price is NT$6,618
NT$6,618
NT$9,235 total
includes taxes & fees
May 7 - May 8
Ad

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
- Pool
- Hot tub
- Spa
- Pet friendly
8.8 out of 10, Excellent, 1,003 reviews
8.8
Excellent
1,003 reviews
The price is NT$11,420
NT$11,420
NT$14,601 total
includes taxes & fees
May 12 - May 13
Sign in to view eligible discounts and perks. More rewards for more adventures!
About the neighborhood
Located on the waterfront, Caloosa Cove Resort by CoolVacay is in Matecumbe, a neighborhood in Islamorada. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's landmarks include Indian Key Historic State Park and Hurricane Monument. Take an opportunity to explore the area for water adventures such as swimming. Visit our Islamorada travel guide
View more Condo Rentals in Islamorada
73801 Overseas Hwy, Islamorada, FL, 33036
What's nearby
Anne's Beach6 min walk - 0.5 km
Bud n' Mary's Dive Center10 min drive - 12.2 km
Theater of the Sea18 min drive - 21.8 km- Sunset Drive Beach3 min walk - 0.3 km
- Baker's Cay Resort Beach37 min drive - 45.7 km
Getting around
- Marathon, FL (MTH-Florida Keys Marathon)28 min drive
Restaurants
- Hungry Tarpon Restaurant5 min drive
- Lazy Days Restaurant8 min drive
- Papa Joe’s Waterfront8 min drive
- The Florida Boy Bar And Grill8 min drive
- Habanos Oceanfront Dining2 min walk
About this property
Caloosa Cove Resort by CoolVacay
Condo located in Matecumbe
Caloosa Cove Resort by CoolVacay provides amenities like a marina and a restaurant. Stay connected with free in-room WiFi.
You'll also enjoy perks such as:
- An outdoor pool
- Free self parking
- Smoke-free premises, games, and books
- Outdoor furniture and barbecue grills
Room features
All guestrooms at Caloosa Cove Resort by CoolVacay offer perks such as air conditioning and separate sitting areas, as well as amenities like free WiFi and dining tables.
Extra conveniences in all rooms include:
- Kitchens with blenders and toasters
- 40-inch TVs with cable channels
- Wardrobes/closets, balconies, and separate sitting areas
Similar properties

Lime Tree Bay Resort
Long Key
Lime Tree Bay Resort
Long Key
- On private beach
- Pool
- Pet friendly
- Parking included
9.2 out of 10, Wonderful, 1,226 reviews
9.2
Wonderful
1,226 reviews
The price is NT$5,539
NT$5,539
NT$7,663 total
includes taxes & fees
May 3 - May 4

Amara Cay Resort
Matecumbe
Amara Cay Resort
Matecumbe
- On private beach
- Pool
- Pet friendly
- Restaurant
8.8 out of 10, Excellent, 1,272 reviews
8.8
Excellent
1,272 reviews
The price is NT$9,641
NT$9,641
NT$13,173 total
includes taxes & fees
May 12 - May 13

Matecumbe Resort
Matecumbe
Matecumbe Resort
Matecumbe
- On private beach
- Pool
- Parking included
- Free WiFi
8.8 out of 10, Excellent, 112 reviews
8.8
Excellent
112 reviews

Hadley Resort and Marina
Matecumbe
Hadley Resort and Marina
Matecumbe
- On private beach
- Pool
- Breakfast included
- Pet friendly
7.6 out of 10, Good, 1,002 reviews
7.6
Good
1,002 reviews
The price is NT$4,553
NT$4,553
NT$6,161 total
includes taxes & fees
May 5 - May 6

La Siesta Resort & Villas
Matecumbe
La Siesta Resort & Villas
Matecumbe
- On private beach
- Pool
- Pet friendly
- Air conditioning
8.6 out of 10, Excellent, 1,004 reviews
8.6
Excellent
1,004 reviews
The price is NT$7,281
NT$7,281
NT$10,518 total
includes taxes & fees
Apr 30 - May 1

Treasure Harbor
Islamorada
Treasure Harbor
Islamorada
- Pool
- Parking included
- Free WiFi
- Air conditioning
9.0 out of 10, Wonderful, 148 reviews
9.0
Wonderful
148 reviews
The price is NT$5,439
NT$5,439
NT$10,593 total
includes taxes & fees
Apr 28 - Apr 29

Fairfield Inn & Suites by Marriott Marathon Florida Keys
Marathon
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Marathon
- Pool
- Breakfast included
- Pet friendly
- Free WiFi
9.2 out of 10, Wonderful, 1,107 reviews
9.2
Wonderful
1,107 reviews
The price is NT$6,844
NT$6,844
NT$7,700 total
includes taxes & fees
May 10 - May 11

Fisher Inn Resort & Marina
Islamorada
Fisher Inn Resort & Marina
Islamorada
- On private beach
- Pool
- Breakfast included
- Pet friendly
8.2 out of 10, Very Good, 1,005 reviews
8.2
Very Good
1,005 reviews
The price is NT$5,412
NT$5,412
NT$7,127 total
includes taxes & fees
May 7 - May 8

Chesapeake Beach Resort
Matecumbe
Chesapeake Beach Resort
Matecumbe
- On private beach
- Pool
- Breakfast included
- Pet friendly
9.2 out of 10, Wonderful, 1,694 reviews
9.2
Wonderful
1,694 reviews
The price is NT$6,618
NT$6,618
NT$9,235 total
includes taxes & fees
May 7 - May 8

Hawks Cay Resort
Marathon
Hawks Cay Resort
Marathon
- On private beach
- Pool
- Hot tub
- Spa
8.0 out of 10, Very Good, 1,016 reviews
8.0
Very Good
1,016 reviews
The price is NT$10,518
NT$10,518
NT$14,056 total
includes taxes & fees
May 12 - May 13
Policies
Check-in
Check-in time starts at 3:00 PM
Late check-in subject to availability
Minimum check-in age: 21
Check-out
Check-out before 10:00 AM
Special check-in instructions
The front desk is open daily from 8:00 AM - 4:00 PM
Guests will receive an email within 2 weeks before arrival with check-in instructions; front desk staffed during limited hours
If you are planning to arrive after 4:00 PM please contact the property in advance using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools
Access methods
Front desk (limited hours)
Pets
Pets not allowed
Children and extra beds
Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available
Property payment types
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards and debit cards; cash is not accepted
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
We should mention
This property does not have elevators
Frequently asked questions
Does Caloosa Cove Resort by CoolVacay have a pool?
Yes, this property has an outdoor pool.
Is Caloosa Cove Resort by CoolVacay pet-friendly?
No, pets are not allowed at this property.
How much is parking?
Self parking is free at this property.
What time is check-in at Caloosa Cove Resort by CoolVacay?
Check-in begins at 3:00 PM. Late check-in is available during limited hours.
What time is check-out at Caloosa Cove Resort by CoolVacay?
Check-out is at 10:00 AM.
Where is Caloosa Cove Resort by CoolVacay located?
Located in Matecumbe, this condo building is within a 10-minute walk of Sunset Drive Beach and Anne's Beach. Robbie’s of Islamorada and Fiesta Key are also within 6 mi (10 km).
Have a question?
Get instant answers with AI powered search of property information and reviews.
Reviews
8.8