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

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

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

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

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

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

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

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
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

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

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

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

$1,991.94 USD total for 3 nights

Oct 26 – 29, 2026

Outdoor hot tub with comfortable seating and dining area
Relaxing private hot tub
Bright living room with comfortable seating
Second bedroom with queen bed and blue accents
Fully equipped kitchen with granite countertops

Reynolds Paradise

2 bedrooms·2 baths
Key West • Florida

$5,369.57 USD total for 28 nights

May 31 – Jun 28, 2027

Private patio with outdoor dining and comfortable lounge seating
Bright living room with comfortable seating and exposed wood ceiling
Shared swimming pool surrounded by tropical landscaping
Well equipped kitchen with modern appliances and granite counters
Inviting private porch with comfortable outdoor seating

Old Town Key West Cottage

2 bedrooms·1½ baths
Key West • Florida

$8,080.01 USD total for 28 nights

Apr 15 – May 13, 2027

Well appointed kitchen with generous counter space
Charming decorative details throughout the home
Inviting primary suite with king bed and private outdoor access
Comfortable living room with French doors and natural light
Quiet porch tucked into a peaceful tropical setting

Casa Mamisa

2 bedrooms·2 baths
Key West • Florida

$16,191.50 USD total for 28 nights

Mar 1 – 29, 2027

Relax on the spacious second floor front porch with comfortable seating, surrounded by lush tropical greenery and beautiful views of historic Old Town Key West.
Private heated swimming pool surrounded by lush tropical gardens, creating a peaceful and secluded oasis in the heart of historic Old Town Key West.
Elegant living room with comfortable seating, a fireplace, large windows, and original architectural details that showcase the character of this historic Key West home.
Third floor primary suite featuring a king bed, vaulted wood ceilings, a cozy sitting area, and beautiful architectural details.
Lush tropical backyard surrounding the private swimming pool, offering a peaceful place to relax and enjoy the laid back atmosphere of Key West.

William Skelton Home - Upstairs

3 bedrooms·2 baths
Key West • Florida

$2,404.05 USD total for 3 nights

Oct 26 – 29, 2026

Lush tropical gardens surround the private swimming pool, creating a peaceful oasis in the heart of Key West’s historic Old Town.
Elegant first floor living room featuring comfortable seating, a fireplace, large windows, and classic Key West architectural details.
The historic William Skelton Home, a beautifully preserved Key West residence surrounded by tropical landscaping in the heart of Old Town.
Relax on the spacious second floor porch with comfortable seating, surrounded by lush tropical landscaping and the beautiful architecture of historic Key West.
Third floor primary suite with vaulted wood ceilings, comfortable seating, a king bed, and beautiful architectural details.

William Skelton Home

6 bedrooms·4 baths
Key West • Florida

$3,322.90 USD total for 3 nights

Oct 26 – 29, 2026

Living-room with sofa bed
Outdoor
Living room/ Dining room
Decoration
Living room

Happier in the Keys, Waterfront Tiny Home

2 bedrooms·1 bath
Key Largo • Florida

$858.75 USD total for 3 nights

Nov 24 – 27, 2026

Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool

Keys Waterfront- Spectacular Gulf View, Dock, Pool

3 bedrooms·1 bath
Marathon • Florida
4.5(10 reviews)

$2,602.13 USD $2,480.46 USD total for 7 nights

Oct 26 – Nov 2, 2026

Private Pool & Tiki Hut
Aerial2
Home from Street
sunset from our balcony
Enjoy lunch under the Tiki

Tropical Pool Home - Tiki Hut & 60' Dock

2 bedrooms·2 baths
Marathon • Florida

$2,203.00 USD total for 7 nights

Oct 26 – Nov 2, 2026

Plunge into this relaxing salt water pool with 3 waterfalls and spa with pool spillover. Once you get in, you won`t want to get out.
The endless Atlantic Ocean view awaits you. Relaxing is easy in the many chill out spots on the beach.
What could be better than your own private beach 3 levels of balconies give maximum access for viewing the ocean.
Kick back in style with a book and a cocktail while experiencing the amazing ocean breezes.
Take a break from lounging in the sun at the pool cabana while enjoying some snacks.

Casa Feliz Luxury Oceanfront w/Private Beach, Pool

4 bedrooms·4 baths
Marathon • Florida

$8,606.25 USD total for 7 nights

Oct 26 – Nov 2, 2026

Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets

Marathon Sleeps 8 | Hot Tub • Game Room • Pets

3 bedrooms·2 baths
Miami • Florida
4.9(29 reviews)

$2,442.91 USD total for 7 nights

Nov 27 – Dec 4, 2026