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 gesamt für 28 Nächte

5. Nov. – 3. Dez. 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 gesamt für 3 Nächte

5.–8. 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)

2.602,13 $ USD 2.480,46 $ USD gesamt für 7 Nächte

5.–12. 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)

3.057,25 $ USD gesamt für 4 Nächte

11.–15. Nov. 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

1.640,00 $ USD gesamt für 7 Nächte

7.–14. Nov. 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)

2.565,00 $ USD gesamt für 3 Nächte

29. Nov. – 2. Dez. 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)

12.012,75 $ USD gesamt für 28 Nächte

12. Apr. – 10. Mai 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 gesamt für 28 Nächte

31. Mai – 28. Juni 2027

Charming Studio with porch - great location!
Charming Studio with porch - great location!
Charming Studio with porch - great location!
Charming Studio with porch - great location!
Charming Studio with porch - great location!

Charming Studio with porch - great location!

1 bedroom·1 bath
Key West • Florida

4.941,00 $ USD gesamt für 28 Nächte

25. Nov. – 23. Dez. 2026

Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location

Old Town 1B Apartment / Balcony / Great Location

1 bedroom·1 bath
Key West • Florida

3.460,00 $ USD gesamt für 28 Nächte

1.–29. März 2027

Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District

Garden Apartment Sanctuary in Historic District

0 bedrooms·1 bath
Key West • Florida
5(7 reviews)

7.304,63 $ USD gesamt für 28 Nächte

1.–29. März 2027

Old Town Gated Studio, Great Location, Great Value
Queen murphy bed below, queen loft bed above.
Loft queen bed
Queen Murphy Bed
Old Town Gated Studio, Great Location, Great Value

Old Town Gated Studio, Great Location, Great Value

0 bedrooms·1 bath
Key West • Florida
5(6 reviews)

4.397,63 $ USD gesamt für 28 Nächte

2.–30. Dez. 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)

4.709,25 $ USD gesamt für 28 Nächte

30. Nov. – 28. Dez. 2026

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 gesamt für 7 Nächte

27. Feb. – 6. März 2027

Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval

Coral Palms 1BR/King/Queen, Pool, block to Duval

1 bedroom·1 bath
Key West • Florida
5(64 reviews)

21.471,75 $ USD gesamt für 28 Nächte

14. Jan. – 11. Feb. 2027

Living Area
Breakfast Bar with seating for 4
Duval Corner - Pet friendly with Balcony
Duval Corner - Pet friendly with Balcony
Duval Corner - Pet friendly with Balcony

Duval Corner - Pet friendly with Balcony

1 bedroom·1 bath
Key West • Florida

972,00 $ USD gesamt für 3 Nächte

9.–12. Nov. 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)

9.646,75 $ USD gesamt für 28 Nächte

1.–29. Apr. 2027

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)

9.329,50 $ USD gesamt für 7 Nächte

2.–9. Jan. 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 gesamt für 28 Nächte

6. Dez. 2026 – 3. Jan. 2027

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

4.006,75 $ USD gesamt für 3 Nächte

6.–9. Dez. 2026

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

3.087,90 $ USD gesamt für 3 Nächte

6.–9. Dez. 2026

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 gesamt für 28 Nächte

15. Apr. – 13. Mai 2027

Duval & Catherine St
Duval & Catherine St
Duval & Catherine St
Duval & Catherine St
Duval & Catherine St

Duval & Catherine St

2 bedrooms·1 bath
Key West • Florida

10.052,00 $ USD gesamt für 28 Nächte

2.–30. Apr. 2027