Apartment holiday rentals in Islamorada

A serene beach scene is depicted at dusk, featuring two palm trees framing the view. The water reflects a soft glow from the moon, while subtle lighting along the beach highlights the sandy area. A kayak rests on the shore, adding to the tranquil atmosphere.

4.92 out of 5 average rating, 201 reviews

Escape to the Seaside - Tiburon Cottage

Our one bedroom suite features separate bedroom and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large in-suite space with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it’s your home.

A modern studio is showcased, featuring a comfortable queen-sized bed and lounge area equipped with a Smart TV. Natural light floods the space from large windows. The kitchen is outfitted with stainless steel appliances, while the outdoor area includes tiki huts with thatched roofs, ideal for relaxation.

4.89 out of 5 average rating, 329 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

A jet ski glides across calm turquoise waters, leaving a white wake behind. Two individuals are seated on the jet ski, enjoying the clear skies and bright clouds above. Lush greenery lines the distant shoreline, creating a serene backdrop.

4.84 out of 5 average rating, 269 reviews

5. Guest's Favorite: Waterfront Apt in Key Largo!

Embrace the tranquil waterfront lifestyle in Key Largo! Revel in picturesque boat views and indulge in freshly caught dishes served at nearby restaurants. Observe the serene presence of manatees, nurse sharks, and a variety of fish leisurely gliding through the canal. Conveniently dock your boat at the Pilot House Marina nearby. Our unit boasts a Modern, Spacious, and Impeccably Clean atmosphere, featuring Private Parking, Wifi, YouTubeTV, Refreshingly Cool AC, Plush Pillows, and a Cozy bed.

5 out of 5 average rating, 23 reviews

Ocean Pointe | Pool, Hot Tub, View, Beach, Parking

Ocean Pointe beach condo — magnificent views, resort amenities & steps to the water. ★ "The view from the balcony is even better than the pictures." ➪ Resort access (pool + hot tub) ➪ Balcony w/ ocean + pool views ➪ Private beach access w/ sunloungers ➪ Fully equipped + stocked kitchen ➪ Keurig + drip coffee maker ➪ Tennis/pickleball courts ➪ BBQ grill + picnic tables ➪ Parking lot (2 cars) 5 mins → DT Tavernier (cafes, dining, shopping) 15 mins → John Pennekamp Coral Reef State Park

A light-filled living area showcases a grey sofa adorned with decorative pillows. A round coffee table sits in the center, surrounded by a textured area rug. The space is complemented by a large pendant light and a wall featuring natural wood art, enhancing the relaxed ambiance.

4.89 out of 5 average rating, 110 reviews

Ocean Pointe 2309 with Ocean Views

Come and enjoy all the activities the Florida Keys has to offer from this new inviting oceanfront condo. Your vacation begins the moment you drive into our 60 acre Ocean Pointe property. The Jr. Olympic sized heated pool is surrounded by beautiful landscaping, a hot tub, & the Mermaid bar. Other amenities include: a sandy beach, a Marina for boats up to 28ft, a ramp, tennis courts, pickle ball court, children's swings, charcoal grills, picnic tables, pier, cafe bar & lounging areas.

5 out of 5 average rating, 32 reviews

Oceanfront Bliss • Wall-to-Wall Water Views + Pool

The options for fun and adventure are unlimited! From the multitude of activities on property, to the variety of water sports and other adventures in the Key Largo surrounding area, you can be sure that you will bring home memories that will last a lifetime. Ocean Pointe Suites at Key Largo offers a variety of activities including tennis and swimming. Fishing, diving, ECO Tours and sailing are available only a short distance from the Ocean Pointe Suites at Key Largo

A welcoming living room features two comfortable green sofas and a coffee table, set against large sliding glass doors that offer ocean views. Decorative lamps add a soft light, while a vibrant area rug enhances the space's warmth and connects with the outdoor scenery.

4.83 out of 5 average rating, 261 reviews

Breathtaking Oceanfront Views at Tropical Daze

New Island Grill Pool Bar & Marina Cafe now open! Deluxe 2/2 right on the ocean, offering spectacular views of the purple and aquamarine waters of Tavernier Key. Jr Olympic Pool with hot tub. Resort community has a beach, iconic pier, marina, tennis & pickle ball. Gated entry with 24 hour security! Perfect location with popular waterfront restaurants, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

A welcoming entrance features a door labeled '8A' and is flanked by two red chairs with blue and white striped cushions. A small table rests between them, surrounded by potted plants. A window offers a glimpse of natural light within the unit.

4.87 out of 5 average rating, 115 reviews

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat sofa and a small dining table with 2 chairs. Private bathroom. AC will keep you cool. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Optional boat slip can be rented for $25/night Efficiency has a 2 person maximum occupancy - no exceptions.

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.86 out of 5 average rating, 145 reviews

Beachside Unit 22 - Private Beach on Atlantic

Unit 22 Details: Main Floor, Walk-in Shower, 2 Queen Beds and Queen Sofa Pull-out, Maximum Occupancy 4 Guests, Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

5 out of 5 average rating, 21 reviews

Waterfront Escape | Pool, Tiki, Breakfast & Marina

Stay at Mystic Mermaid, a brand-new luxury 1BR/1BA Waterfront Villa that sleeps up to 4 guests. Located on a scenic canal in the heart of the Florida Keys, this elegant retreat offers marina views and resort-style amenities including a pool, Tiki Bar, restaurant, pickleball & sand volleyball courts, fitness center, and complimentary breakfast. Perfectly located between Islamorada and Key West for the ultimate island getaway.

A light-filled living area features a blue sofa with decorative pillows and a wooden coffee table atop a woven area rug. Two accent chairs frame the seating arrangement, while natural decor elements, including tall grasses and wall art, enhance the welcoming ambiance.

4.93 out of 5 average rating, 241 reviews

Top Floor - Oceanview condo with tennis courts, pickleball, hot tub, BBQ, marina & private beach. ★ "Exactly as described & very clean. Beautiful views & a nice peaceful escape." ➠ Resort size heated pool + Jacuzzi ➠ Balcony w/ ocean view ➠ Private beach access w/ sun lounger ➠ Fully equipped + stocked kitchen ➠ Double Master Suites ➠ 55” smart TVs w/ cable ➠ Car park (2 cars max) ➠ 250 Mbps WIFI

4.98 out of 5 average rating, 59 reviews

A bright and airy living area features large windows that invite natural light. Modern furnishings include a turquoise sofa and two high tables with blue metal chairs. Colorful decor is provided by oversized paintbrushes mounted on the wall, enhancing the playful ambiance.

Apartment in Islamorada

Elevated Retreat | Sunset Access + Boat Basin

Elevated, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Set above the trees for a more open, airy feel, yet tucked into a peaceful setting. Enjoy walkable access to restaurants, shops, and breweries, plus fast WiFi and everything needed for a comfortable Keys getaway 🌴

Popular amenities for Islamorada apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

An aerial view of the beachfront condo building is captured, revealing its three stories and proximity to the ocean. Surrounding palm trees enhance the tropical ambiance, while the serene blue water reflects sunlight. A small parking area is visible in front of the property.

4.84 out of 5 average rating, 19 reviews

Seaside Villa~ Charming Beachfront Condo w/ Pool!

A corner two-story townhouse is shown, situated beside a tranquil saltwater lagoon. Lush greenery surrounds the property, and a staircase leads to a diving platform over the water. The reflection of the structure and trees can be seen on the still lagoon surface.

4.99 out of 5 average rating, 180 reviews

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

A spacious living area features large windows that offer views of the marina and ocean. Comfortable seating arrangements include two leather sofas and a stylish coffee table. Natural light brightens the space, while wood paneling adds a modern touch to the decor.

4.84 out of 5 average rating, 45 reviews

Overlooking Marina/Ocean view

4.92 out of 5 average rating, 24 reviews

Marathon Getaway•5 Min to Sombrero Beach•Sleeps 4

A sandy beachfront area is presented, featuring several white Adirondack chairs arranged around a small table. Soft clouds drift overhead, and the ocean extends into the horizon. Decorative string lights are visible above, enhancing the outdoor setting.

4.92 out of 5 average rating, 12 reviews

Kawama New Listing!

5 out of 5 average rating, 22 reviews

#1 Island Hideaway 89 - OCEAN FRONT

Apartment in Key Colony Beach

5 out of 5 average rating, 3 reviews

*NEW* Coral Sands Oceanfront-Beach & Pool

Apartment in Islamorada

5 out of 5 average rating, 3 reviews

Eclectic Easeful Stay!

Private apartment rentals

An outdoor balcony features two comfortable chairs and a small wooden table. Lush palm trees and greenery are visible, framed by a clear sky and distant water views, creating a peaceful setting for relaxation.

5 out of 5 average rating, 18 reviews

Gorgeous Moon Bay Condo Heated Pool Beach

A spacious living area features a light-toned sectional sofa arranged around a central coffee table. A large television is positioned on a wooden stand. Soft lighting is provided by lamps, and decorative artwork adorns the walls, enhancing the open and airy feel of the space.

4.76 out of 5 average rating, 54 reviews

Sombrero Beach 2 bedroom apartment close to Beach!

4.53 out of 5 average rating, 15 reviews

Private Studio cabana Style with Spa Hot Tub

A spacious living area is showcased with a large gray sectional sofa and a round wooden coffee table. Natural light is let in through expansive sliding glass doors that lead to a balcony. Decorative art and plants add subtle details to the decor.

5 out of 5 average rating, 54 reviews

Key Largo, Florida - Gem by the Sea

A two-story building is situated beside a calm lagoon, surrounded by lush greenery. Screened balconies are visible on the upper level, offering views of the water. Kayaks are placed near the shoreline, complementing the tranquil outdoor environment.

4.91 out of 5 average rating, 43 reviews

Lagoon-front family townhome

A spacious balcony is viewed, showcasing a railing that frames a scenic waterfront. Below, a community swimming pool is visible, surrounded by palm trees and lounge chairs. The horizon displays boats docked in the calm water, complemented by a clear blue sky.

5 out of 5 average rating, 7 reviews

Paradise in The Anchorage Resort Key Largo

5 out of 5 average rating, 6 reviews

Florida Keys Tropical Coastal Condo!

A spacious suite features a soft king bed with elegant bedding. Two patterned armchairs are positioned near a window, allowing natural light to illuminate the room. A flat-screen TV is mounted on the wall, and a view of the tropical garden is visible outside.

4.69 out of 5 average rating, 29 reviews

Azul del Mar Tropical Garden Suite (Palma)

Apartment rentals with a hot tub

A bright living area features large windows, allowing natural light to fill the space. Soft blue walls complement the light-colored furnishings, including a spacious curved sofa and a distinctive wooden coffee table. A ceiling fan circulates air, while a decorative plant adds a touch of greenery.

5 out of 5 average rating, 13 reviews

New Coastal Escape 2BR/2BA Oceanfront Condo

5 out of 5 average rating, 3 reviews

1BR-Oceanview Key Largo Condo | Pool* Marina*Beach

A tranquil beach scene features several blue lounge chairs arranged in neat rows on the sandy shore. A wooden pier extends into the water, accompanied by a thatched-roof gazebo. Lush greenery and a peaceful sky with scattered clouds complete the coastal vista.

4.99 out of 5 average rating, 94 reviews

Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft

The open-plan living area features a vibrant blue sofa with colorful cushions, complemented by two orange chairs. A round wooden coffee table sits atop a large, patterned rug. A green wall with decorative foliage and a neon sign adds a lively touch, with windows providing natural light and views of the outside.

5 out of 5 average rating, 96 reviews

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA

A bright living area features a comfortable gray sofa, decorative chairs, and a coffee table on a patterned rug. Natural light floods the space through large windows, creating a relaxed atmosphere. A wall-mounted TV and a small desk can also be seen, along with coastal decor.

4.9 out of 5 average rating, 90 reviews

When Paradise is Key: Tropical Oceanfront Condo

4.93 out of 5 average rating, 14 reviews

New Key Largo- Ocean Pearl, Pickleball, Restaurant

A tranquil pool area features lounge chairs arranged around a crystal-clear pool. Palms sway gently nearby, and a tiki bar with a roof can be seen in the background, overlooking calm waters. The sky transitions to a soft blue as evening approaches.

5 out of 5 average rating, 4 reviews

Marathon Studio on Lovely Gulf Front Resort

A cozy living area features a comfortable sofa adorned with colorful cushions. A round glass dining table surrounded by chairs is positioned near large sliding doors that provide access to a balcony with views. A flat-screen TV and a decorative table complete the space.