Four Bedroom Ocean View Villas at The Islands of Islamorada

United States / Florida / Florida Keys

From sunrise over the water to evenings spent unwinding in the island air, the Four Bedroom Ocean View Villas offer a setting where every moment feels intentional and unforgettable. Welcome to relaxed luxury—Islamorada style.

up to 4
Bedrooms
up to 8
Guests
4
Bathrooms
Min. Nights Upon Request

Overview

Discover elevated island living in the Four Bedroom Ocean View Villas at The Islands of Islamorada. Thoughtfully designed for spacious comfort and effortless coastal elegance, these private villas offer breathtaking ocean views and an inviting retreat for families and groups seeking a refined Florida Keys escape.

Each villa features expansive indoor and outdoor living areas, allowing guests to gather, relax, and reconnect while surrounded by the natural beauty of Islamorada. Floor-to-ceiling windows frame the Atlantic, filling the interiors with natural light and gentle ocean breezes. Whether hosting unforgettable family moments or enjoying a tranquil getaway with friends, these villas have balance, privacy, luxury, and laid-back island living.

Villa Highlights~

  • Expansive four-bedroom villa
  • Balcony or terrace with breathtaking ocean views
  • Elegant coastal décor with high-end furnishings
  • Open-concept living and dining areas
  • Fully equipped gourmet kitchen with premium appliances
  • Flat-screen TVs
  • Cable programming
  • Elevator (in 2 villas | on request)
  • Two-car garage

The Islands of Islamorada~

Gracefully set along the turquoise waters of the Florida Keys, the Islands of Islamorada is a secluded oceanfront sanctuary where refined luxury meets the natural beauty of island life. Designed as an intimate, resort-style enclave, the property is framed by lush tropical landscaping, serene water views, and an atmosphere of effortless sophistication.

Guests are invited to experience a curated collection of upscale amenities created for both leisure and indulgence. An oceanfront tiki bar offers handcrafted cocktails in a relaxed yet elegant setting, while two resort-style pools provide tranquil spaces for sun-drenched afternoons. The private beach delivers a sense of rare seclusion, with soft sands and sweeping ocean views that invite moments of quiet reflection.

Resort Amenities~

  • Tranquil private beach
  • Private marina with boat slips
  • Oceanfront bar
  • Fitness facility
  • Two sparkling swimming pools
  • Jacuzzi
  • Watersports
  • Pickleball courts
  • Oceanside golf tee
  • Games (horseshoes, corn hole, ladder ball, board games)
  • Playground
  • Grill stations
  • Two fire pits
  • Parking

Dining~

Dining at The Islands of Islamorada is a relaxed yet refined experience, inspired by the flavors, freshness, and unhurried rhythm of the Florida Keys. At the heart of the property, the oceanfront tiki bar offers a casual, open-air setting where handcrafted cocktails and light fare are served just steps from the water.  In addition, an on-site chef can prepare an array of breakfast and lunch selections to enjoy in-room. With panoramic ocean views and warm island breezes, it’s the perfect place to linger from sunlit afternoons into golden-hour evenings.

Beyond the resort, Islamorada is celebrated as the culinary capital of the Florida Keys, offering an exceptional collection of waterfront restaurants, fresh seafood experiences, and chef-driven dining just moments away. Guests can savor locally inspired cuisine featuring freshly caught fish, tropical ingredients, and globally influenced flavors—all served in settings that range from elegant and intimate to relaxed and lively.

Resort Marina~

The Islands of Islamorada Marina offers seamless dockage for guests arriving by boat, providing a convenient and secure option for those bringing their own vessels. The on-site manager is available to assist with coordinating dock space, ensuring a smooth arrival and effortless stay on the water.

For guests eager to explore the legendary waters of the Florida Keys, private flats fishing boats can be arranged for the duration of your visit. Venture into pristine backcountry flats, crystal-clear channels, and world-renowned fishing grounds, where unforgettable days unfold amid stunning natural beauty. Whether you’re navigating at sunrise or returning at dusk, the marina serves as your gateway to an elevated island boating experience.

Poolside~

The two oceanfront pools and spa provide an elegant setting for relaxation and refined family enjoyment. Take in sweeping ocean views as you swim, unwind on expansive sun decks, or indulge in the soothing warmth of the hot tub. Thoughtfully designed with both serenity and sophistication in mind, each space offers a seamless blend of comfort, beauty, and island tranquility.

Watersports~

Discover an elevated world of aquatic adventure at The Islands of Islamorada, where the turquoise waters of the Florida Keys become your playground. Set out by kayak or paddleboard and glide effortlessly across crystal-clear seas, exploring the vibrant shoreline at your own pace. For those drawn to the exhilaration of the open water, Hobie Cat sailing offers a thrilling yet graceful way to harness the ocean breeze.

Wellness~

Fitness Center: Stay energized at the Ocean House 24-hour fitness center, where maintaining your routine is seamless—even while on island time. The fully equipped gym features state-of-the-art cardio machines, modern strength-training equipment, and a full selection of free weights. Thoughtfully designed to support workouts of every level, the space allows you to train at your own pace while enjoying the balance of wellness and relaxation in the Florida Keys.

Yoga Classes: As the sun rises, join us for a rejuvenating experience designed to awaken both body and mind. The experienced instructors guide you through a graceful flow of poses and mindful breathing, thoughtfully curated for all levels. Surrounded by breathtaking scenery and the calming rhythms of nature, each session offers a moment of balance, clarity, and renewal to begin your day.

Pickleball: Whether you’re a seasoned player or discovering the game for the first time, these impeccably maintained facilities and breathtaking surroundings create an exceptional setting for both spirited competition and effortless connection. Enjoy an engaging match with friends or fellow guests, where every rally is elevated by the energy of the game and the beauty of the natural landscape that surrounds you.

 


Amenities

4 Bedrooms, 4 Bathrooms

Sleeps 8 Guests

3100 Interior Square Ft.

  • Full Air Conditioning
  • Children's Playground
  • Oceanside Golf Tee
  • High-Speed Wireless Internet
  • Non-Motorized Equipment
  • 24-Hour Fitness Center
  • Cardio Machines
  • Strength Training Equipment
  • Free Weights
  • Weddings
  • Small Celebrations
  • Washer
  • Dryer
  • Iron
  • Ironing Board
  • En-Suite Bathrooms (select)
  • Double Vanity
  • Lighted Makeup Mirror
  • Bathrobe
  • Bed Linens
  • Walk-In Closets
  • Flat-Screen TV
  • Phone
  • Alarm Clock
  • Island
  • Refrigerator
  • Stove
  • Oven
  • Microwave
  • Dishwasher
  • Toaster
  • Coffee Maker
  • Tea Kettle
  • Blender
  • Balcony/Terrace
  • Living Area
  • Dining Area
  • Gourmet Kitchen
  • Elevator (2 villas)
  • Two-Car Garage
  • Room Safe
  • Gated Community
  • Grilling Stations
  • Flat-Screen TVs
  • Cable Programming
  • Two Oceanfront Pools
  • Sun Decks
  • Sun Loungers
  • Umbrellas
  • Private Beach
  • Private Marina
  • Two Pool
  • Poolside Tiki Bar
  • Grill Stations
  • Fire Pit
  • Playground
  • Pickleball
  • Games
  • Fitness Center
  • Oceanside Golf Tee
  • In-Room Spa Services (fee required)

Details

Bedroom Details

Bedroom #1: King-size bed with en-suite bathroom
Bedroom #2: King-size bed with en-suite bathroom
Bedroom #3: King-size bed with en-suite bathroom
Bedroom #4: Two twin-size beds

Beach Details

Step onto the private, sun-kissed beach, where soft sands and turquoise waters set the stage for unforgettable island moments. Elegant loungers and shaded cabanas provide a serene escape for adults seeking relaxation, while gentle waves and shallow waters invite children to play safely along the shore. Stroll hand-in-hand with loved ones, build sandcastles, or simply soak in the breathtaking ocean views. Thoughtfully designed for both refined comfort and family enjoyment, this beachfront is the perfect blend of tranquility, fun, and island luxury.

Pool Details

Two resort pools
Jacuzzi

Distance Details

Distance from Airport Ft. Lauderdale International Airport (FLL) - 108 miles; 2 hours
Miami International (MIA) – 78 miles; 1.5 hours
Marathon Private Airport (MTH) – 31.4 miles; 45 minutes
Key West International Airport (EYW) - 80.6 miles; 2 hours

Staff and Services

Dedicated concierge service and planning
24-hour on-site assistance
Area dining reservations, activities & excursions planning
Complimentary yoga classes

Staff and Services (at Additional Cost)

Daily housekeeping is available for an additional fee and must be reserved in advance, and is subject to availability.
Private chef services
In-room spa services from local therapists
First-class seaplane services with Tropic Ocean Airways
Pantry stocking
Fireside S’mores
Shoreline fishing
Fishing charters in the “Sportsfishing Capital of the World.”
Golf cart rentals

Location Details

Nestled in the heart of the Florida Keys, The Islands of Islamorada offer an unparalleled oceanfront retreat. Situated on a private stretch of coastline, the resort provides breathtaking views of the turquoise waters of the Atlantic Ocean and Florida Bay. Just a short drive from the lively village of Islamorada, guests enjoy convenient access to world-class dining, shopping, and local attractions while still savoring the privacy and tranquility of an exclusive island getaway. Perfectly positioned for boating, fishing, and water adventures, the resort is a serene haven for those seeking both adventure and relaxation amid the natural beauty of the Keys.

Villa Notes

Images are representative of the property’s overall quality. Décor, bedding, and fixtures may vary between individual units.
Pets:
Not all villas are pet-friendly. Please check with your Villa Specialist to confirm availability.
Up to two dogs are allowed per villa. A pet fee of $50 per dog, per night (plus tax) applies.
Certified service dogs are welcome at the property at no additional charge. All dogs must be registered prior to arrival by completing a Service Animal / Pet Waiver.


Exclusive Offers

Your next escape, rewarded. The world's most extraordinary villas deserve to be experienced — and now, they come with a return. Receive up to $1,000 cashback, paid upon deposit, simply for booking the trip you've been dreaming of.

Amount based on the booking value:

$5,000 – $14,999 = $200 Cashback
$15,000 – $49,999 = $500 Cashback
$50,000 – $100,000 = $750 Cashback
$100,001+ = $1,000 Cashback

Offer valid for new bookings made between 5/22/26 - 6/13/26. Amount is based on the base villa cost only (excluding taxes and fees). Minimum booking value applies ($5,000.00).Cash back will be paid in a Villas of Distinction Visa® Prepaid Card upon deposit. Villas of Distinction Visa® Prepaid Card is issued by MetaBank®, N.A., Member FDIC, pursuant to a license from Visa U.S.A. Inc. No cash access or recurring payments. Can be used everywhere Visa debit cards are accepted. Card valid for up to 12 months; unused funds will forfeit after the valid thru date. Card terms and conditions apply. Offer is valid for direct clients OR travel advisors’ clients. The Villas of Distinction Prepaid Card will be mailed directly to the direct client OR travel advisors’ client within 30 days of deposit. Client mailing address must be provided. May not be combinable with other offers. All offers are subject to availability and may not apply to all villas or travel dates. Other restrictions may apply; please call for full details.

Rates and Availability

Tax Service Charge Details*
Florida State Sales Tax: 7.5%
Occupancy Tax: 5%
Resort Fee: $49 (per night, plus tax)
Accidental Damage Waiver
A $299 Accidental Damage Waiver applies to every reservation.
Minimum Stay Details
High/Low Season: 2-night minimum stay required
Holidays: 3-5 night minimum stay required
Check-In Times
Check in: 04:00 PM - Check out: 11:00 AM
Rate Policies
Please note that calendars are not available for this property. Your Villa Specialist will be happy to check availability for you.

Location

Villa information may change without notice and should be confirmed with our villa rental specialists.