Saltwater House — Oceanfront Villa with Dock
Saltwater House — Oceanfront Villa with Dock
Saltwater House — Oceanfront Villa with Dock
Saltwater House — Oceanfront Villa with Dock
Saltwater House — Oceanfront Villa with Dock

Saltwater House — Oceanfront Villa with Dock

4 bedrooms·3 baths
Islamorada • Florida
5(14 reviews)

$1,455.00 USD total for 3 nights

Oct 20 – 23, 2026

Brand New - Oceanfront Condo
Brand New - Oceanfront Condo
Brand New - Oceanfront Condo
Brand New - Oceanfront Condo
Brand New - Oceanfront Condo

Brand New - Oceanfront Condo

2 bedrooms·2 baths
Islamorada • Florida

$2,255.00 USD total for 7 nights

Oct 20 – 27, 2026

This is a view taken at sunrise from our balcony.
Forever changing tropical colors
Living area with full ocean view and sliding doors that open to screeed in balcony
Oceanfront with unbelievable views
Nice tropical beach setting tennis court, tiki huts, and bbq grill

Oceanfront with unbelievable views

2 bedrooms·2 baths
Tavernier • Florida
4.8(5 reviews)

$2,245.00 USD total for 7 nights

Oct 20 – 27, 2026

Keys Escape with Privet Beach & 70' Dock
Keys Escape with Privet Beach & 70' Dock
Keys Escape with Privet Beach & 70' Dock
Keys Escape with Privet Beach & 70' Dock
Keys Escape with Privet Beach & 70' Dock

Keys Escape with Privet Beach & 70' Dock

3 bedrooms·2 baths
Islamorada • Florida

$6,995.00 USD total for 28 nights

Oct 20 – Nov 17, 2026

Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed

Walk to Beach + Dining, 2BR, King Bed

2 bedrooms·1 bath
Tavernier • Florida

$845.60 USD total for 3 nights

Oct 20 – 23, 2026

Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath

Cozy Keys Stay | King Bed + Luxe Bath

1 bedroom·1 bath
Tavernier • Florida

$761.60 USD total for 3 nights

Oct 20 – 23, 2026

Modern Coastal Suite | Walk to Beach + Dining
Modern Coastal Suite | Walk to Beach + Dining
Modern Coastal Suite | Walk to Beach + Dining
Modern Coastal Suite | Walk to Beach + Dining
Modern Coastal Suite | Walk to Beach + Dining

Modern Coastal Suite | Walk to Beach + Dining

1 bedroom·1 bath
Tavernier • Florida

$677.60 USD total for 3 nights

Oct 20 – 23, 2026

[Beach] Exclusive access to private beach
[Picnic table]
[Boardwalk] Great place to take a stroll
[Boardwalk] Shaded sitting area
[Kitchen] Fully stocked & equipped

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

2 bedrooms·2 baths
Tavernier • Florida
5(99 reviews)

$877.50 USD total for 3 nights

Oct 30 – Nov 2, 2026

Toes in the Sand - Huge Pool, Ocean View, Pool Cafe, Marina Cafe
Huge heated Pool with cafe
Hot tub
Living room with open living space
Kitchen

Toes in the Sand - Huge Pool, Ocean View, Pool Cafe, Marina Cafe

2 bedrooms·2 baths
Tavernier • Florida
5(1 review)

$750.83 USD total for 3 nights

Nov 15 – 18, 2026

Beautiful Sunrises on the Jetty
Marina Cafe
Huge Swimming Pool with food and drinks, alcohol drinks, too!
Large Hot Tub
Queen Size Sleeper Sofa and Converter Chair

Florida Keys Getaway - Huge Pool, Beach, Amenities

1 bedroom·1 bath
Tavernier • Florida

$634.50 USD total for 3 nights

Oct 26 – 29, 2026

[Beach] Exclusive access to private beach
[Pier] Ocean view seating
[Aerial view] Shared pool & hot tub
[Kitchen] Fully equipped & stocked
[Tennis courts]

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

2 bedrooms·2 baths
Tavernier • Florida

$965.34 USD total for 3 nights

Oct 24 – 27, 2026

Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!

Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!

3 bedrooms·3 baths
Key Largo • Florida

$2,026.99 USD total for 3 nights

Oct 25 – 28, 2026

Chic Ocean Hideaway with Grill
Chic Ocean Hideaway with Grill
Chic Ocean Hideaway with Grill
Chic Ocean Hideaway with Grill
Chic Ocean Hideaway with Grill

Chic Ocean Hideaway with Grill

3 bedrooms·2 baths
Key Largo • Florida

$3,606.65 USD total for 3 nights

Nov 6 – 9, 2026

Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub

3 bedrooms·3 baths
Key Largo • Florida

$2,969.34 USD total for 3 nights

Oct 30 – Nov 2, 2026

New Oceanside Paradise with Pool and Waterfront Views!
New Oceanside Paradise with Pool and Waterfront Views!
New Oceanside Paradise with Pool and Waterfront Views!
New Oceanside Paradise with Pool and Waterfront Views!
New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!

3 bedrooms·3 baths
Key Largo • Florida

$2,739.59 USD total for 3 nights

Oct 31 – Nov 3, 2026

Oceanview Escape – Pool, Hot Tub & Private Deck!
Oceanview Escape – Pool, Hot Tub & Private Deck!
Oceanview Escape – Pool, Hot Tub & Private Deck!
Oceanview Escape – Pool, Hot Tub & Private Deck!
Oceanview Escape – Pool, Hot Tub & Private Deck!

Oceanview Escape – Pool, Hot Tub & Private Deck!

3 bedrooms·3 baths
Key Largo • Florida
Oasis Pool at Sunset
Oasis Pool with sunrise
Oasis Pool Oceanside
Living area sunroom overlooking the pool with Queen Sleeper Sofa
Sunroom with private stairway entrance to the largest pool in the Florida Keys overlooking the ocean.

Sunrise Retreat with Ocean & Pool Views, Gym, PB Courts,Gameroom

3 bedrooms·3 baths
Key Largo • Florida

$2,011.60 USD total for 3 nights

Nov 1 – 4, 2026

Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!

Waterfront Luxe Pool, Hot Tub, Theater, Games and More!

5 bedrooms·5 baths
Key Largo • Florida

$10,743.75 USD total for 3 nights

Sep 26 – 29, 2027

Breathtaking Sunrises
Upstairs living area overlooking marina and ocen.
Kitchen with seating island
Kitchen
Upstairs open living concept

Sunrise Escape - Ocean View Villa , Pool, Sunrises

3 bedrooms·3 baths
Key Largo • Florida
5(2 reviews)

$1,459.35 USD total for 3 nights

Oct 28 – 31, 2026

Aerial view of the Kawama Yacht Club complex showing the octagonal Tower Building, deep-water marina, ocean jetty, tennis/pickleball courts, and direct turquoise oceanfront access with Beach.
Welcome to the Oasis Pool ! Sun, Fun, Relax and repeat !
Beachfront at Kawama, Tiki's, Seating,Barbecues, Fire-Pits, Ocean Access
LUXURY Living RE-IMAGINED, More SPACE, More VALUE, More KEYS
Chef Ready Gourmet Kitchen, Professional S Steel & Designer Equipment

Key Largo Oceanfront Resort: Kawama Tower 406

2 bedrooms·2 baths
Key Largo • Florida
5(216 reviews)

$1,897.50 USD $1,644.38 USD total for 6 nights

Oct 22 – 28, 2026

Watch boats glide toward Pilot House Marina from turquoise Adirondack chairs on your private patio at Cabana 4. From local regattas to offshore rallies, Waterfront Cabanas offers front-row seats to Key Largo's best boating events.
Sit back and take in vibrant turquoise waters gliding past your private patio at Cabana 4. From your front-row seat on the canal, watch tarpon roll beneath the surface and the sun dip behind lush mangroves.
Catch your favorite shows on YouTubeTV, or log into your own streaming apps on the smart TV at Cabana 4. The real view is right outside - open the door to canal breezes and dock views blending indoor comfort with the Keys outdoors.
Your Key Largo escape begins at Cabana 4, where turquoise chairs and sun-drenched grounds set the scene. Steps from the calm canal and minutes from Pennekamp Park, this private coastal sanctuary is all yours.
Experience unforgettable Key Largo sunsets from Cabana 4's private patio. Watch boats drift along the canal as golden skies glow over the palms - your perfect Florida Keys getaway awaits.

4. Cozy Key Largo Waterfront Apartment | Dive

1 bedroom·1 bath
Key Largo • Florida
4.85(346 reviews)

$746.56 USD total for 3 nights

Oct 20 – 23, 2026

Sit back and take in vibrant turquoise waters gliding past your private patio at Cabana 6. From your front-row seat on the canal, watch tarpon roll beneath the surface and the sun dip behind lush mangroves.
Coastal art and soft textiles dress the lounge at Cabana 6. Curl up with a book between adventures, cool AC humming, canal views through the glass just steps away.
Stretch out on the green turf at Cabana 6, where palms sway over calm canal waters. Pull up a turquoise chair, grab a cold drink, and let the gentle coastal rhythm of the Florida Keys take over.
Tucked amidst swaying palms and dense hedges, Cabana 6 offers pure privacy. Pause under rustling fronds, breathe in fresh saltwater air, and ease into the unhurried rhythm of Key Largo island life.
Golden light washes over the lawn at Cabana 6, where the seawall meets calm canal waters. This is slow-morning territory - coffee in hand, pelicans cruising past, the Florida Keys unfolding at island pace.

6. Key Largo Waterfront Apartment | Dock, Snorkel

1 bedroom·1 bath
Key Largo • Florida
4.89(299 reviews)

$713.83 USD total for 3 nights

Oct 25 – 28, 2026

Sit back and take in vibrant turquoise waters gliding past your private patio at Cabana 5. From your front-row seat on the canal, watch tarpon roll beneath the surface and the sun dip behind lush mangroves.
Soft morning light streams across the plush queen bed and warm cedar wall at Cabana 5. Step right outside into the gentle canal breeze to start another Florida Keys day at your own unhurried pace.
Stretch out on the green turf at Cabana 5, where palms sway over calm canal waters. Pull up a turquoise chair, grab a cold drink, and let the gentle coastal rhythm of the Florida Keys take over.
Golden light washes over the lawn at Cabana 5, where the seawall meets calm canal waters. This is slow-morning territory - coffee in hand, pelicans cruising past, the Florida Keys unfolding at island pace.
Your Key Largo escape begins at Cabana 5, where turquoise chairs and sun-drenched grounds set the scene. Steps from the calm canal and minutes from Pennekamp Park, this private coastal sanctuary is all yours.

5. Key Largo Waterfront Apartment | Reef & Relax

1 bedroom·1 bath
Key Largo • Florida
4.84(277 reviews)

$740.80 USD total for 3 nights

Oct 20 – 23, 2026

End your day at Cabana 1 with a stunning Key Largo sunset, peaceful canal views, drifting boats, and tropical skies. Relax on the private patio with a refreshing drink and soak in the laid-back beauty of your Florida Keys getaway.
Soft morning light streams across the plush queen bed and warm cedar wall. Step right outside into the gentle canal breeze to start another Florida Keys day at your own unhurried pace at this waterfront retreat.
Sit back and take in the vibrant turquoise waters gliding past your private patio. From your front-row seat on the canal, watch tarpon roll beneath the surface, boats drift out toward the reef, and the sun dip behind lush green mangroves capturing KeyLargo
Rest easy steps from the seawall, where a plush queen bed rests against a warm cedar-plank wall. With quiet split-system AC and coastal art, this waterfront retreat is a cool sanctuary built for days on the Key Largo water.
Your Key Largo escape begins at Cabana 1, where turquoise chairs and a chilled white wine set the scene. Steps from the calm canal and minutes from Pennekamp Park, this private coastal sanctuary is all yours.

1. Key Largo Waterfront Apartment | Canal & Ocean

1 bedroom·1 bath
Key Largo • Florida
4.82(271 reviews)

$771.34 USD total for 3 nights

Oct 20 – 23, 2026