Entire condo

Caloosa Cove Resort by CoolVacay

Waterfront condo in Islamorada with outdoor pool and restaurant

Choose dates to view prices

Wed, Apr 15
Thu, Apr 16
April 2026
1
May 2026
A great choice for a stay in Islamorada, Caloosa Cove Resort by CoolVacay features a marina. After having fun at the outdoor pool, you can grab a bite to eat at the restaurant. Condos feature conveniences like kitchens, along with balconies and free WiFi.
Excellent

Popular amenities

  • Pool
  • Free parking
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Child-friendly activities

Main amenities (9)

  • 30 condos
  • Marina
  • Near the beach
  • Restaurant
  • Outdoor pool
  • Air conditioning
  • Picnic area
  • Barbecue grills
  • Limited hour front desk

Feel at home (6)

  • Kitchen
  • Separate sitting area
  • Television
  • Coffee/tea maker
  • Blackout drapes/curtains
  • Barbecue grill(s)

Room options

Showing 30 of 30 rooms
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Pool View

  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Pool View

  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony

  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 1 Queen Bed, 1 Double Sofa Bed and 1 Queen Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

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
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Marina View

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony

  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Double Sofa Bed and 1 Queen Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • Marina view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

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
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Ocean View

  • Ocean view
  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Standard Studio, Balcony, Ocean View

  • Ocean view
  • 400 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

Deluxe Suite, 1 Bedroom, Balcony, Pool View

  • 800 sq ft
  • 1 bedroom
  • Sleeps 6
  • 2 Queen Beds and 1 Double Sofa Bed
Towels
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets
Blackout drapes, iron/ironing board, free WiFi, bed sheets

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

Similar properties

Private beach, white sand, sun loungers, beach towels
  • Pool
  • Free breakfast
  • Pet friendly
  • Free WiFi
9.2
Wonderful
1,680 reviews
$283 nightly
$318 total
Apr 15 - Apr 16
Total with taxes and fees
Chesapeake Beach Resort
Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
  • Pool
  • Pet friendly
  • Air conditioning
  • Bar
8.6
Excellent
1,001 reviews
$279 nightly
$313 total
Apr 14 - Apr 15
Total with taxes and fees
La Siesta Resort & Villas
Balcony
  • Pool
  • Spa
  • Free parking
  • Restaurant
9.2
Wonderful
1,306 reviews
$317 nightly
$357 total
Apr 22 - Apr 23
Total with taxes and fees
Cheeca Lodge & Spa
5 outdoor pools, cabanas (surcharge), pool umbrellas
  • Pool
  • Spa
  • Parking available
  • Free WiFi
8.0
Very Good
1,010 reviews
$377 nightly
$423 total
Apr 26 - Apr 27
Total with taxes and fees
Hawks Cay Resort
Balcony view
  • Pool
  • Free breakfast
  • Pet friendly
  • Free parking
7.6
Good
1,000 reviews
$195 nightly
$219 total
Apr 20 - Apr 21
Total with taxes and fees
Hadley Resort and Marina
Exterior
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
9.2
Wonderful
1,007 reviews
$351 nightly
$395 total
Apr 15 - Apr 16
Total with taxes and fees
Islander Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
8.8
Excellent
1,004 reviews
$319 nightly
$355 total
Apr 2 - Apr 3
Total with taxes and fees
Drop Anchor
25-inch flat-screen TV with digital channels, TV
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
9.0
Wonderful
148 reviews
$313 nightly
$352 total
Apr 16 - Apr 17
Total with taxes and fees
Treasure Harbor
Bar (on property)
  • Pool
  • Free breakfast
  • Pet friendly
  • Parking available
9.2
Wonderful
1,106 reviews
$224 nightly
$252 total
Apr 26 - Apr 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Exterior
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
9.6
Exceptional
239 reviews
$234 nightly
$263 total
Apr 12 - Apr 13
Total with taxes and fees
Ragged Edge Resort & Marina
Compare similar properties
Mod logo
Earn OneKeyCash on thousands of hotels when you sign in and book. More rewards for more adventures!

About the neighborhood

Map
73801 Overseas Hwy, Islamorada, FL, 33036

What's nearby

  • Sunset Drive Beach - 3 min walk - 0.3 km
  • Anne's Beach - 6 min walk - 0.5 km
  • Bud n' Mary's Dive Center - 10 min drive - 12.2 km
  • Theater of the Sea - 18 min drive - 21.8 km
  • Baker's Cay Resort Beach - 37 min drive - 45.7 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 28 min drive
  • Key West Intl. Airport (EYW) - 92 min drive
  • Miami Intl. Airport (MIA) - 121 min drive
  • Miami, FL (MPB-Public Seaplane Base) - 123 min drive
  • Miami, FL (OPF-Opa Locka Executive) - 128 min drive

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬5 min drive
  • ‪Lazy Days Restaurant - ‬8 min drive
  • ‪Papa Joe’s Waterfront - ‬8 min drive
  • ‪The Florida Boy Bar And Grill - ‬8 min drive
  • ‪Tiki Bar at Amara Cay Resort - ‬8 min drive

About this property

Caloosa Cove Resort by CoolVacay

A great choice for a stay in Islamorada, Caloosa Cove Resort by CoolVacay features a marina. After having fun at the outdoor pool, you can grab a bite to eat at the restaurant. Condos feature conveniences like kitchens, along with balconies and free WiFi.

At a glance

Property size

    • 30 condos

Arriving/Leaving

    • Check-in time starts at 3:00 PM
    • Late check-in subject to availability
    • Minimum check-in age: 21
    • Check-out time is 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

Required at check-in

    • Credit card required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 21

Children

    • No cribs (infant beds)

Pets

    • Pets not allowed

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms (speed: 25+ Mbps)

Parking

    • Free uncovered onsite self parking

Property amenities

Food and drink

  • Restaurant
  • Barbecue grills

What to do

  • Fishing
  • Beach nearby

Services

  • Front desk (limited hours)

Facilities

  • Picnic area
  • An outdoor pool
  • Marina
  • Outdoor furniture

Room amenities

Be entertained

  • 40-inch TV
  • Cable TV channels

Home comfort

  • Air conditioning and heating
  • Coffee/tea maker
  • Iron/ironing board

Sleep well

  • Blackout drapes/curtains
  • Bed sheets provided

What to enjoy

  • Balcony
  • Separate sitting area

Freshen up

  • Towels

Stay connected

  • Free WiFi (speed of 25+ Mbps)
  • Phone

Food and drink

  • Kitchen
  • Toaster
  • Blender
  • Dining table

Fees & policies

Policies

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.
This property does not have elevators.
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 accepts credit cards and debit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover

Frequently asked questions

Is there a pool at Caloosa Cove Resort by CoolVacay?

Yes, there's an outdoor pool.

Are pets allowed at Caloosa Cove Resort by CoolVacay?

Sorry, pets aren't allowed.

Is parking offered on site at Caloosa Cove Resort by CoolVacay?

Yes, there's free self parking.

What are the check-in and check-out times at Caloosa Cove Resort by CoolVacay?

You can check in starting at 3:00 PM. Check-out time is 10:00 AM.

What is there to do at Caloosa Cove Resort by CoolVacay and nearby?

Have fun during the warmer months with activities such as fishing. Enjoy a swim in the outdoor pool or use the condo's other amenities, which include a picnic area.

Are there restaurants at or near Caloosa Cove Resort by CoolVacay?

Yes, there's an onsite restaurant.

Does Caloosa Cove Resort by CoolVacay have a kitchen or kitchenette?

Yes, there is a kitchen which also includes a blender, a coffee maker, and a toaster.

Does Caloosa Cove Resort by CoolVacay have any outdoor private spaces?

Yes, this condo features a balcony.

What's the area around Caloosa Cove Resort by CoolVacay like?

Caloosa Cove Resort by CoolVacay is a short 6-minute walk from Anne's Beach and 3 minutes' walk from Sunset Drive Beach.

Have a question?

Get instant answers with AI powered search of property information and reviews.

8.8

Excellent