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 totaal voor 28 nachten

18 nov – 16 dec 2026

Mad Mahi Canal front w/pool
Mad Mahi Canal front w/pool
Mad Mahi Canal front w/pool
Mad Mahi Canal front w/pool
Mad Mahi Canal front w/pool

Mad Mahi Canal front w/pool

4 bedrooms·3½ baths
Summerland Key • Florida
5(3 reviews)

$ 15.069,31 USD totaal voor 28 nachten

18 nov – 16 dec 2026

Summerland Nest -Beautiful views
Summerland Nest -Beautiful views
Summerland Nest -Beautiful views
Summerland Nest -Beautiful views
Summerland Nest -Beautiful views

Summerland Nest -Beautiful views

7 bedrooms·4½ baths
Summerland Key • Florida
5(1 review)

$ 24.819,33 USD totaal voor 28 nachten

18 nov – 16 dec 2026

Latitudes-Ocean Front Pool
Latitudes-Ocean Front Pool
Latitudes-Ocean Front Pool
Latitudes-Ocean Front Pool
Latitudes-Ocean Front Pool

Latitudes-Ocean Front Pool

6 bedrooms·4 baths
Cudjoe Key • Florida
5(12 reviews)

$ 4.241,70 USD totaal voor 5 nachten

29 nov – 4 dec 2026

Blue Palms Retreat
Blue Palms Retreat
Blue Palms Retreat
Blue Palms Retreat
Blue Palms Retreat

Blue Palms Retreat

3 bedrooms·2 baths
Cudjoe Key • Florida
5(6 reviews)

$ 1.884,30 USD totaal voor 4 nachten

20–24 nov 2026

Family Retreat
Family Retreat
Family Retreat
Family Retreat
Family Retreat

Family Retreat

6 bedrooms·4 baths
Summerland Key • Florida
4.89(9 reviews)

$ 6.187,77 USD totaal voor 7 nachten

15–22 mei 2027

Tropical Paradise
Tropical Paradise
Tropical Paradise
Tropical Paradise
Tropical Paradise

Tropical Paradise

3 bedrooms·2½ baths
Cudjoe Key • Florida
4.67(6 reviews)

$ 4.671,33 USD totaal voor 7 nachten

29 mei – 5 jun 2027

Front of House
pool
Kitchen Island
Kitchen
Dining Room

Fandango

5 bedrooms·3 baths
Cudjoe Key • Florida

$ 6.129,02 USD totaal voor 7 nachten

13–20 feb 2027

7 Seas Home
7 Seas Home
7 Seas Home
7 Seas Home
7 Seas Home

7 Seas Home

3 bedrooms·3 baths
Little Torch Key • Florida
5(5 reviews)

$ 9.213,26 USD totaal voor 28 nachten

18 nov – 16 dec 2026

pool
5 Pirate's Hideaway
5 Pirate's Hideaway
5 Pirate's Hideaway
5 Pirate's Hideaway

5 Pirate's Hideaway

3 bedrooms·2½ baths
Little Torch Key • Florida
5(2 reviews)

$ 9.441,18 USD totaal voor 28 nachten

18 nov – 16 dec 2026

Little Torch Key Nest
Little Torch Key Nest
Little Torch Key Nest
Little Torch Key Nest
Little Torch Key Nest

Little Torch Key Nest

6 bedrooms·4½ baths
Little Torch Key • Florida
4.88(8 reviews)
$658 – $685/ nacht(excl. kosten & belastingen)
Conch House -Ocean front -Dock
Conch House -Ocean front -Dock
Conch House -Ocean front -Dock
Conch House -Ocean front -Dock
Conch House -Ocean front -Dock

Conch House -Ocean front -Dock

4 bedrooms·3½ baths
Little Torch Key • Florida
5(5 reviews)

$ 6.322,87 USD totaal voor 7 nachten

5–12 dec 2026

Starfish House
Starfish House
Starfish House
Starfish House
Starfish House

Starfish House

3 bedrooms·2 baths
Little Torch Key • Florida
5(2 reviews)

$ 5.036,07 USD totaal voor 7 nachten

21–28 nov 2026

Secluded Hideaway -pool & dock
Secluded Hideaway -pool & dock
Secluded Hideaway -pool & dock
Secluded Hideaway -pool & dock
Secluded Hideaway -pool & dock

Secluded Hideaway -pool & dock

3 bedrooms·2 baths
Big Pine Key • Florida

$ 5.408,66 USD totaal voor 28 nachten

18 nov – 16 dec 2026

Sunrise Retreat - Great Views
Sunrise Retreat - Great Views
Sunrise Retreat - Great Views
Sunrise Retreat - Great Views
Sunrise Retreat - Great Views

Sunrise Retreat - Great Views

3 bedrooms·2 baths
Big Pine Key • Florida

$ 12.904,46 USD totaal voor 28 nachten

18 nov – 16 dec 2026

20 - Sugarloaf Oasis
20 - Sugarloaf Oasis
20 - Sugarloaf Oasis
20 - Sugarloaf Oasis
20 - Sugarloaf Oasis

20 - Sugarloaf Oasis

0 bedrooms·4½ baths
Summerland Key • Florida

$ 10.920,87 USD totaal voor 28 nachten

22 nov – 20 dec 2026

This is it, this the yacht you will be staying on. It like a luxury floating 2 bedroom condo with a lot more to offer, think of all the outdoor areas. The vessel is available for private charter, if interested enquire for a quote.
An other angle view of the yacht. Notice the comfortable aft deck seating with awning for shade, the upper deck sun pad and if you look closely you can upper helm deck seating too.
Overhead view of the yacht. On the bow you can see the huge sun pad with room for all. Its also a great place to hang at night as guest have described enjoying stargazing while laying on this pad.
An other great view of FreeTime, she is really this pretty inside and out.
FREE TIME Vibes image 5

FREE TIME Vibes

2 bedrooms·2 baths
Key West • Florida
5(5 reviews)

$ 3.706,00 USD totaal voor 3 nachten

18–21 nov 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)

$ 2.962,13 USD $ 2.822,46 USD totaal voor 7 nachten

18–25 nov 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)

$ 2.236,00 USD totaal voor 4 nachten

29 nov – 3 dec 2026

Exterior
Room
Interior
Dining
Private kitchen

NEW LISTING! Island house. Dog friendly 3 bedroom 2 bath home in Marathon!

3 bedrooms·2 baths
Marathon • Florida

$ 1.780,00 USD totaal voor 7 nachten

19–26 dec 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)

$ 2.270,25 USD totaal voor 3 nachten

29 nov – 2 dec 2026

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
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)

$ 12.110,63 USD totaal voor 28 nachten

12 apr – 10 mei 2027

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 totaal voor 28 nachten

31 mei – 28 jun 2027