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

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

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

A View from the Backyard
Hose from the Water (yellow house)
Unobstructed View, 38' Deep Water Dock
Sunset from Yard
Kitchen

Waterfront Home - Incredible View, 37' Dock, Kayak

2 bedrooms·2 baths
Marathon • Florida
4.77(13 reviews)

$1,584.00 USD total for 7 nights

Oct 26 – Nov 2, 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

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

View of Cove from Backyard
Another Great Sunset
Home from the Water (Yellow)
Living Room
Kitchen

Waterfront Keys Home - Spectacular View, 37' Dock

2 bedrooms·2 baths
Marathon • Florida
4.33(3 reviews)

$1,408.00 USD total for 7 nights

Oct 31 – Nov 7, 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

Fire table and sitting area near pool watching boats pass through canal.
Resort style inground pool and hot tub.
Inground hot tub, floating double jet ski dock.
Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean
Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean

Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean

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

$14,536.40 USD total for 28 nights

Oct 26 – Nov 23, 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 26 – Nov 2, 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 26 – Nov 23, 2026