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

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

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

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

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)
Breathtaking open views of the Gulf of America, right from your private dock
Your private pool and stunning gulf views await at Caribbean Sunsets
Enjoy breathtaking sunsets right from the comfort of the house
Dive into relaxation with your private pool and hot tub, surrounded by lush tropical greenery
Dine with a stunning Gulf-front view right on your private patio

Caribbean Sunsets: Open Gulf Views with Private Dock and Pool

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

$3,442.75 USD total for 7 nights

Nov 14 – 21, 2026

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)

$1,413.53 USD total for 3 nights

Oct 28 – 31, 2026

Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool
Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool
Relax in paradise with our brand-new hot tub, added March 2025, just 0.5 blocks from Duval Street! 🏝️💦 Perfect for unwinding after a day of Key West adventures.
Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool
Bright and open kitchen and dining area, perfect for cooking meals and gathering around the table. Enjoy all the comforts of home with plenty of space to dine and relax.

Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool

2 bedrooms·2 baths
Key West • Florida
5(1 review)

$9,682.00 USD total for 28 nights

Apr 1 – 29, 2027

Kittyhouse on Catherine, Tropical Pool, Parking
Breakfast bar
full kitchen
2nd floor bathroom
first floor half bathroom

Kittyhouse on Catherine, Tropical Pool, Parking

2 bedrooms·1½ baths
Key West • Florida
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)

$773.15 USD total for 3 nights

Nov 15 – 18, 2026

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

$1,835.35 USD total for 3 nights

Nov 17 – 20, 2026

Sunny tropical patio with bistro set, grill & French doors
Sunny studio with lounge nook, queen bed, AC & dining table
Cozy loft retreat with skylight, TV, and built-in storage.
Bright modern kitchen with stainless suite, gas range, and dining nook
Sleek bath with frameless walk-in shower, bench, and subway tile

Beach House Modern Old Town Studio Near Duval

1 bedroom·1 bath
Key West • Florida
5(1 review)

$5,305.50 USD total for 28 nights

Nov 30 – Dec 28, 2026