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

Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed
Walk to Beach + Dining, 2BR, King Bed

Walk to Beach + Dining, 2BR, King Bed

2 bedrooms·1 bath
Tavernier • Florida

$845.60 USD total for 3 nights

Oct 26 – 29, 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

Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath
Cozy Keys Stay | King Bed + Luxe Bath

Cozy Keys Stay | King Bed + Luxe Bath

1 bedroom·1 bath
Tavernier • Florida

$761.60 USD total for 3 nights

Oct 26 – 29, 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

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

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

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

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

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

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

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