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

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 26 – 29, 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

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

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

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

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

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

$561.65 USD $526.64 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

$781.08 USD total for 3 nights

Oct 26 – 29, 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

Bright living room with comfortable seating and historic Key West character
Refreshing swimming pool surrounded by tropical landscaping
Compact kitchen with everything needed for a comfortable stay
Private balcony overlooking the colorful streets of Duval Street
Inviting living space with exposed wood ceiling and Smart TV

Shipwreck Suite

1 bedroom·1 bath
Key West • Florida

$5,937.28 USD total for 28 nights

Dec 6, 2026 – Jan 3, 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