Welcome to Stay Anchored at Sombrero. View from across the canal.
Open floor plan - kitchen, dining room and living room.
Fully-stocked kitchen.
Living room with sectional, two accent chairs and entertainment console.
Main Entrance Side & Stairs

Stay Anchored at Sombrero

4 bedrooms·3 baths
Marathon • Florida
5(19 reviews)

$4,432.46 USD total for 7 nights

Feb 27 – Mar 6, 2027

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)

$686.83 USD total for 3 nights

Oct 26 – 29, 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 26 – Nov 1, 2026

End your day at Cabana 6 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.
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.
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.
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, Cabana 6 is a cool sanctuary built for days on the Key Largo water.
Cook effortlessly with a stainless Whirlpool fridge, electric stove, dishwasher, and granite breakfast bar at Cabana 6. Savor fresh catches from Key Largo Fisheries or prepare stone crabs right inside your private waterfront retreat.

6. Key Largo Waterfront Apartment | Dock, Snorkel

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

$692.73 USD total for 3 nights

Oct 26 – 29, 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)

$692.73 USD total for 3 nights

Oct 26 – 29, 2026

This is the beautiful pool directly on the beach along with a 10 man hot tub
just a beautiful shot of the pool
Living Room with queen pullout couch
large leather couch, love seat and recliner 55 inch flat screen tv with comcast sliders head out to the 40 ft balcony
living room with wet bar

KW Luxury 2/2 Beachfront resort Tropical Oasis

2 bedrooms·2 baths
Key West • Florida
4.92(200 reviews)

$1,679.13 USD total for 4 nights

Oct 26 – 30, 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)

$692.73 USD total for 3 nights

Oct 26 – 29, 2026

Nestled in a charming row of six waterfront retreats, Cabana 3 glows under the Key Largo sunset. Watch boats drift down calm canal waters from bright turquoise patio chairs made for evening drinks.
Sunlight streams across sleek granite counters and polished white cabinets at Cabana 3. Whether plating fresh catches from the nearby marina or pouring morning drip coffee, this open kitchen brings breezy coastal elegance to every meal.
Soft morning light streams across the plush queen bed and warm cedar wall at Cabana 3. Step right outside into the gentle canal breeze to start another Florida Keys day at your own unhurried pace.
Kick back on dual plush daybeds in a sun-drenched living space at Cabana 3. Stream live shows on YouTubeTV, then step right out onto your private back patio where calm canal views deliver true Florida Keys bliss.
Catch your favorite shows on YouTubeTV, or log into your own streaming apps on the smart TV at Cabana 3. The real view is right outside - open the door to canal breezes and dock views blending indoor comfort with the Keys outdoors.

3. Waterfront Key Largo Apartment | Scuba & Dock

1 bedroom·1 bath
Key Largo • Florida
4.78(258 reviews)

$692.73 USD total for 3 nights

Oct 26 – 29, 2026

Golden light washes over the lawn at Cabana 2, 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.
Soft morning light streams across the plush queen bed and warm cedar wall at Cabana 2. Step right outside into the gentle canal breeze to start another Florida Keys day at your own unhurried pace.
Catch your favorite shows on YouTubeTV, or log into your own streaming apps on the smart TV at Cabana 2. The real view is right outside - open the door to canal breezes and dock views blending indoor comfort with the Keys outdoors.
End your day at Cabana 2 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.
Sunlight streams across sleek granite counters and polished white cabinets at Cabana 2. Whether plating fresh catches from the nearby marina or pouring morning drip coffee, this open kitchen brings breezy coastal elegance to every meal.

2. Waterfront Key Largo Apartment | Fish & Relax

1 bedroom·1 bath
Key Largo • Florida
4.78(239 reviews)

$717.87 USD total for 3 nights

Oct 26 – 29, 2026

Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ

Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ

3 bedrooms·2 baths
Marathon • Florida
4.94(16 reviews)

$2,924.00 USD total for 7 nights

Oct 26 – Nov 2, 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)

$1,044.00 USD total for 3 nights

Nov 8 – 11, 2026

Huge seasonally heated pool
Tropical tiki bar with BBQ grill and bright seating—al fresco fun
Bright open-plan living with cozy sleeper sectional, dining, and kitchen
Two queen beds on third floor
Sunny bedroom with King bed and playful cat quilt, cozy lighting and ample storage.

Cathouse Old Town Oasis Huge Heated Pool & Parking

4 bedrooms·2½ baths
Key West • Florida
5(72 reviews)

$1,941.75 USD total for 3 nights

Oct 26 – 29, 2026

Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval

Coral Palms 1BR/King/Queen, Pool, block to Duval

1 bedroom·1 bath
Key West • Florida
5(64 reviews)

$21,886.88 USD total for 28 nights

Jan 14 – Feb 11, 2027

Living room
Front house
Indoor living room and kitchen
Living room
Kitchen

Happy in the Keys Tiny Home with Boat Ramp

3 bedrooms·1 bath
Key Largo • Florida
5(62 reviews)

$847.25 USD total for 3 nights

Oct 29 – Nov 1, 2026

Enjoy a serene walk along the beach, mere steps from your condo.
Large Heated Pool
Enjoy a serene walk along the beach, mere steps from your condo.
Large Heated Pool
Enjoy pool and ocean views from the patio.

Coastal Charm: Steps from the Beach, 2BR/2BA Condo, Pool View

2 bedrooms·2 baths
Marathon • Florida
5(11 reviews)

$1,621.50 USD total for 7 nights

Oct 31 – Nov 7, 2026

Beach
Outdoor dining
Beach
Beach
Outdoor dining

Tropical Keys sanctuary steps from private beach.

2 bedrooms·2 baths
Key Colony Beach • Florida
4.89(142 reviews)

$2,140.00 USD total for 7 nights

Oct 26 – Nov 2, 2026

Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District

Garden Apartment Sanctuary in Historic District

0 bedrooms·1 bath
Key West • Florida
5(7 reviews)

$7,324.88 USD total for 28 nights

Mar 1 – 29, 2027

Old Town Gated Studio, Great Location, Great Value
Queen murphy bed below, queen loft bed above.
Loft queen bed
Queen Murphy Bed
Old Town Gated Studio, Great Location, Great Value

Old Town Gated Studio, Great Location, Great Value

0 bedrooms·1 bath
Key West • Florida
5(6 reviews)

$4,819.50 USD total for 28 nights

Dec 2 – 30, 2026

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.
Unwind in your private tropical oasis, where lush greenery surrounds a serene pool. Sip your morning coffee or enjoy an al fresco meal on the spacious deck
Take a dip in your private pool, tucked away amidst lush, tropical foliage. Perfect for a refreshing morning swim or a relaxing evening-this retreat invites you to embrace the laid-back charm of the Keys.

Casa Rosa: Historic Key West Home with Pool, 1 Block from Duval

4 bedrooms·4 baths
Key West • Florida
5(9 reviews)

$9,403.53 USD total for 7 nights

Jan 2 – 9, 2027

Enjoy your own private movie theater, promising cinematic magic in a serene ambiance under the stars. You can also dip into your own private hot tub and enjoy a movie, the stars and the calm & private twilight hues
Craving a morning or afternoon coffee? We have you covered with your very own coffee making Keurig machine and if you want an espresso, we have a nespresso machine too. The kitchen comes with espresso/coffee pods to flavor your coffee just right
Family movie nights just got an upgrade—unwind under the stars with a cozy family film, all set beneath the shade of our beautiful tropical tree. **Some photos include lightly enhanced or staged scenes to help show how the space can be enjoyed.
Family movie nights just got an upgrade—unwind under the stars with a cozy family film, all set beneath the shade of our beautiful tropical tree. **Some photos include lightly enhanced or staged scenes to help show how the space can be enjoyed.
Enjoy your very own pool for summer cool-offs. You can also relax on a lounge chair and soak in the evening serenity

Keys Getaway - Pool, Hot Tub & Movie Theater

3 bedrooms·3 baths
Marathon • Florida

$3,813.75 USD total for 7 nights

Oct 26 – Nov 2, 2026

Condo #15, located on the 2nd floor, offers stunning ocean views and has two screened balconies
Condo #15, located on the 2nd floor, offers stunning ocean views and is depicted in the right building in this photo
Spacious Living Area
Large Heated Pool
Large Heated Pool with loungers

Bird of Paradise: Oceanfront Condo 3 BR, 2 BA with Heated Pool

3 bedrooms·2 baths
Marathon • Florida
5(6 reviews)

$2,173.75 USD total for 7 nights

Nov 7 – 14, 2026

Open Gulf Views with Private Pool and Dock
Oceanfront Paradise: Your Private Oasis
Oceanfront Paradise: Your Private Oasis
Golden hour over the Gulf of America—experience breathtaking sunsets from your private paradise
Spacious patio featuring a pool, hot tub, and comfortable lounge chairs

Tropical Sunsets: Open Gulf Views with Private Dock and Pool

4 bedrooms·3 baths
Marathon • Florida
5(4 reviews)

$4,145.40 USD total for 7 nights

Nov 14 – 21, 2026

Private tropical plunge pool with waterfall and sunny brick patio
Elegant Old Town gem with double porches and a white picket fence
Bright, open living room with comfy seating and coastal flair
Spacious chef’s kitchen with granite, stainless appliances, and patio access
Sunny dining room for 10 with hardwoods, French doors, and ceiling fan

Cockhouse 3BR/3BA Privt Pool/Parking/Pets Old Town

3 bedrooms·3 baths
Key West • Florida
5(1 review)

$8,509.50 USD total for 28 nights

Oct 26 – Nov 23, 2026

Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats

Marathon Gulfside Lake view home, bring your boats

4 bedrooms·3½ baths
Marathon • Florida
$1,000/ night(excl. fees & taxes)