Sleepfare

Drop Anchor

★★★ 84959 Overseas Highway, 222, Islamorada, Florida, 33036, Islamorada, US

8.8 guest rating· 154 reviews

About this hotel

Escape to paradise at Drop Anchor, where stunning waterfront views meet exceptional comfort.

Private Beach & Outdoor Pool

Bask in the sun on our exclusive private beach or take a refreshing dip in the outdoor pool, perfect for a relaxing day under the Florida sun.

Modern Comforts

Our 18 air-conditioned rooms are designed with your comfort in mind, featuring flat-screen televisions, complimentary Wi-Fi, and coffee/tea makers to start your day right.

Business & Leisure Amenities

Take advantage of our convenient business center and enjoy free self-parking. Whether you're here for leisure or work, we cater to all your needs with attentive services and a charming picnic area.

Don’t miss your chance to experience all that Drop Anchor has to offer—book your stay with us today!

Rooms & rates

Pick your dates. Prices are live, not cached.

Oceanfront Trailer

Sleeps 2 · Queen Bed

  • Air conditioning
  • Private bathroom
  • Kitchenette
  • Coffee/tea maker
  • Free WiFi

<p><strong>1 Queen Bed</strong></p><p>Features a private patio</p><br/><p><b>Layout</b> - Bedroom and dining area</p><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Kitchenette with refrigerator, stovetop, oven, and microwave</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Resort View Queen Family Suite w/ Kitchen

Sleeps 6 · Queen Bed, Double bed, Sofa bed

  • Air conditioning
  • Private bathroom
  • Kitchen
  • Coffee/tea maker
  • Free WiFi

<p><strong>1 Queen Bed, 1 Double Bed and 1 Queen Sofa Bed</strong></p><p>Overlooking the resort</p><br/><p><b>Layout</b> - 2 bedrooms and living room</p><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Kitchen with refrigerator, stovetop, oven, and microwave</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking, pet friendly</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Resort View Family Suite w/ Kitchen

Sleeps 6 · 2× Queen Bed, 2× Twin bed

  • Air conditioning
  • Private bathroom
  • Kitchen
  • Coffee/tea maker
  • Free WiFi

<p><strong>2 Queen Beds and 2 Twin Beds</strong></p><p>Overlooking the resort</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Kitchen with refrigerator, oven, cookware/dishware, and coffee/tea maker</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Oceanfront Queen Room

Sleeps 2 · Queen Bed

  • Air conditioning
  • Private bathroom
  • Coffee/tea maker
  • Free WiFi
  • Shower

<p><strong>1 Queen Bed</strong></p><p>Overlooking the ocean</p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Mini-fridge and coffee/tea maker </p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking, pet friendly</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Resort View Queen Room w/ Kitchen & Private Porch

Sleeps 2 · Queen Bed

  • Air conditioning
  • Private bathroom
  • Kitchen
  • Coffee/tea maker
  • Free WiFi

<p><strong>1 Queen Bed</strong></p><p>Overlooking the resort</p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Kitchen with refrigerator, oven, microwave, and cookware/dishware</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Oceanfront King Suite w/ Kitchen & Private Balcony

Sleeps 4 · King bed

  • Air conditioning
  • Private bathroom
  • Kitchenette
  • Coffee/tea maker
  • Free WiFi

<p><strong>1 King Bed</strong></p><p>Balcony with beach views</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Kitchenette with refrigerator, stovetop, oven, and microwave</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Resort View ADA King Room

Sleeps 2 · King bed

  • Air conditioning
  • Private bathroom
  • Coffee/tea maker
  • Free WiFi
  • Shower

<p><strong>1 King Bed</strong></p><p>Patio with garden views</p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Refrigerator and coffee/tea maker </p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Yard and iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Accessibility</b> - Wheelchair accessible</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Ocean View Double Queen w/ Kitchen & Private Balcony

Sleeps 4 · 2× Queen Bed

  • Air conditioning
  • Private bathroom
  • Kitchen
  • Coffee/tea maker
  • Free WiFi

<p><strong>2 Queen Beds</strong></p><p>Features a private balcony</p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Kitchen with coffee/tea maker </p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Ocean View Double Queen Room

Sleeps 4 · 2× Queen Bed

  • Air conditioning
  • Private bathroom
  • Coffee/tea maker
  • Free WiFi
  • Shower

<p><strong>2 Queen Beds</strong></p><p>Balcony with ocean views</p><br/><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Mini-fridge and coffee/tea maker </p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Oceanfront King Suite w/ Beach Walkout & Kitchen

Sleeps 4 · King bed

  • Air conditioning
  • Private bathroom
  • Kitchen
  • Coffee/tea maker
  • Free WiFi

<p><strong>1 King Bed</strong></p><p>Deck/patio with ocean views</p><br/><p><b>Layout</b> - Bedroom </p><p><b>Internet</b> - Free WiFi </p><p><b>Entertainment</b> - Flat-screen TV with premium channels</p><p><b>Food & Drink</b> - Kitchen with refrigerator, oven, cookware/dishware, and coffee/tea maker</p><p><b>Sleep</b> - Premium bedding and bed sheets </p><p><b>Bathroom</b> - Private bathroom, shower, free toiletries, and a hair dryer</p><p><b>Practical</b> - Iron/ironing board</p><p><b>Comfort</b> - Air conditioning and daily housekeeping</p><p><b>Need to Know</b> - Limited housekeeping</p><p>Non-Smoking</p><p>Room is accessed via exterior corridors </p><p>Connecting/adjoining rooms can be requested, subject to availability </p>

Amenities

  • Free WiFi
  • Pool sun loungers
  • Free self parking
  • Beach sun loungers
  • Beach towels
  • Beach umbrellas
  • Private beach nearby
  • Front desk (limited hours)
  • Safe-deposit box at front desk
  • Banquet hall
  • Boat tours nearby
  • Designated smoking area
  • Dock
  • Ecotours nearby
Show all 35 amenities
  • Fish cleaning table
  • Fishing nearby
  • Free bicycles on site
  • Garden
  • Hiking/biking trails nearby
  • Marina nearby
  • Motor boating on site
  • Paddleboard on site
  • Parasailing nearby
  • Picnic area
  • Sailing nearby
  • Scooter/moped rentals nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Stair-free path to entrance
  • Swimming nearby
  • Upper floors accessible by stairs only
  • Walkway to water
  • Wedding services
  • Well-lit path to entrance
  • Wheelchair accessible

Location

© OpenStreetMap contributors

84959 Overseas Highway, 222, Islamorada, Florida, 33036, Islamorada, US

Check-in
from 03:00 PM to 06:00 PM
Check-out
until 11:00 AM

What guests say8.8154 reviews

+ Beautiful location+ Friendly staff+ Clean grounds+ Affordable rates− Old and run-down facilities− Hot water issues− Noisy neighbors
Cleanliness8.5
Service9.2
Location9.3
Room Quality8.2
Amenities8.8
Value for Money8.7

I will visit again.

8.0

Room was clean and tidy. They also have kayaks, paddleboards and bikes you can use and is included with your stay.

− Ice machine was not working.

Ross · US · 2026-07-17

Guest review

9.0

Hébergement de plein pied avec accès et une vue magnifique de la piscine qui domine la mer . Une cuisine bien aménager.

− Manque de chaîne proposer sur la télévision et une wifi avec peu de réserve .

Rémy · FR · 2026-07-11

Easy to check in, room was immaculate and comfortable, it was great!

10.0

It was laid back and comfy

− We liked everything

Chantel · US · 2026-07-11

What a perfect place to stay in older, but nicely remodeled, keys style hotel

10.0

The property is comprised of a few separate buildings with most of the rooms oceanfront. It has great facilities including a boat ramp and dock with direct ocean access. There is also a pool with large tiki hut for dining, and huge open area with palapas and Adirondack chairs for sitting oceanfront. They have bikes, kayaks and games around the large open spaces. Our room was really well sized, clean and very comfortable with an oceanfront balcony, king bed and full kitchen. The best part is the people that work there, they are some of the kindest and most helpful people you hope to find, but seldom do. A special shout out to Donna! What a wonderful lady; helpful, kind and always a huge smile. Really, everyone was great.

Pam · US · 2026-07-09

Enjoyable and friendly. Fair value for holiday weekend.

8.0

Clean, location and facilities

− Rooms can use some updating and cosmetic repairs on room amenities

ira · US · 2026-07-06

Good to know

Pool access available from 7:30 AM to 6:30 PM.

The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation.

Contactless check-out is available.

›Pets

Service animals are exempt from fees/restrictions

›Children and extra beds

No rollaway/extra beds available

›Check-in & Check-out

Contactless check-out is available

›Accessibility

No elevators

›Pets

Pets allowed

›General

Professional property host/manager

›Children and extra beds

No cribs (infant beds) available

›Pets

Only dogs are allowed

›Pets

Service animals are allowed