Private Home Rentals for Vacation on the Florida Keys, Florida, Page 3 of 43

Refine Your Search Start a New Search
Find by availability dates:
and/or by weekly rental rate
(in $ USD):
Current Criteria:
(remove all criteria)

Compare Selected
compare

Bamboo Key

— Property 40025h
Florida Keys condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$1,100 - $5,220/week
compare

# 175 - Venture Out

— Property 7028244h
Florida Keys house rental
1 Bedroom, Sleeps 4,
House, 1 Bathroom, adventure, air-conditioning
Rates - per house (USD)
$850 - $900/week
compare

Casa Atlantica One Bedroom

— Property 20895h
Florida Keys condo rental
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, adventure, beach
Rates - per condo (USD)
$170 - $260/night
$1,120 - $1,820/week
Calendar Updated Nov 23 2009

Property Review

These pictures, though nice and certainly got us there, do not do the place justice! The 2 pictures depicting the LR and DR are actually for one large, gorgeous room with the entire glass wall...
compare

Oceanside Retreat in the Florida Keys (Marathon Mm 50)

— Property 264471
Florida Keys house rental - Canal View - Rear of House
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, near the ocean, waterfront, balcony
Rates - per property (USD)
$950 - $1,100/week
compare

'SIMPLY IRRESISTIBLE' @ The Pool: 2BR 2.5BA Luxurious Poolside Townhome

— Property 206279
Florida Keys townhome rental - The Living Room: Simple elegance & a high-def TV.
2 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, 1 Half Bath, near the ocean, resort, pool
Rates - per property (USD)
$3,600 - $5,000/month
compare

'SOUTHERNMOST BELLE' @ The Annex: 7 Bedrooms, Huge Porches & Large Private Pool

— Property 225064
Florida Keys house rental - A very private yard & a gorgeous pool....
7 Bedrooms, Sleeps 14,
House, 5 Bathrooms, downtown, resort, pool
Rates - per property (USD)
$6,500 - $14,000/week
$20,000 - $35,000/month
Calendar Updated Nov 20 2009

Property Review

We have been renting in Key West for ten years now, and this year was our first time renting "Southernmost Belle". We have already reserved the house for next year, and now wouldn't think of...
compare

'GEORGIA PEACH' in Old Town: 4BR Luxury Home @ the Meadows

— Property 225229
Florida Keys house rental - 'Georgia Peach', on a quiet street in the Meadows
4 Bedrooms, Sleeps 10,
House, 4 Bathrooms, 1 Half Bath, downtown, resort, pool
Rates - per property (USD)
$7,000 - $11,000/month
compare

'TOP 'O THE COPA' @ Duval: Gorgeous Old Town Penthouse, Available Nightly

— Property 229160
Florida Keys condo rental - A fifteen foot ceiling & lots of light...
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, 1 Half Bath, downtown, village, terrace
Rates - per property (USD)
$375 - $400/night
$1,675 - $2,400/week
$5,500 - $6,600/month
Calendar Updated Nov 20 2009

Property Review

We loved the location as we could walk to both the gulf or the ocean from this central location. We were not bothered by any late night noise which you might think would be the case on Duval...
compare

“CASA BLANCA 1888' @ White Street: Private Home in Old Town, 4BR & Large Pool

— Property 238180
Florida Keys house rental - The Master Suite has a balcony with a view...
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, downtown, resort, pool
Rates - per property (USD)
$7,000 - $12,000/month
Calendar Updated Nov 20 2009

Property Review

We frequent key west at least 5 times a year this was the best place we have ever stayed. The home was immaculate the pool was so refreshing on a hot afternoon. Bruce was great checked with us to...
compare

New Key West Condo 2/BR - 2.5/BA

— Property 246336
Florida Keys condo rental - Waterside View of Condos and Clubhouse
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, 1 Half Bath, beach, near the ocean, pool
Rates - per property (USD)
$1,500 - $2,000/week
compare

“NOONA'S MANSION-by-the-SEA”: Oceanfront 6BR/5.5BA @ Truman Annex, Private Pool

— Property 254512
Florida Keys house rental - A gorgeous home in a quiet cul-de-sac
6 Bedrooms, Sleeps 14,
House, 5 Bathrooms, 1 Half Bath, pool, garden
Rates - per property (USD)
$7,700 - $16,000/week
$22,500 - $40,000/month
compare

Bayfront Paradise Heated Pool Home on the Bay in Islamorada

— Property 243094
Florida Keys house rental
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$1,800 - $2,200/week
compare

Tarpon Cove: Best Islamorada Vacation Rental

— Property 153876
Florida Keys house rental - Exterior
3 Bedrooms, Sleeps 6,
House, beach, waterfront, air-conditioning
Rates - per property (USD)
$1,700 - $1,900/week
$6,000/month
Accepts Online Payments
Calendar Updated Nov 20 2009

Property Review

Just wanted to tell you how very much we enjoyed our stay at your rental. The layout of the home is very spacious and yet so very cozy. It really was so relaxing and fun staying there. The...
compare

Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock

— Property 113802
Florida Keys condo rental - View From Corner of Lower Deck, Left
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, 1 Half Bath, near the ocean, waterfront, pool
Rates - per property (USD)
$986 - $1,586/week
$4,444 - $6,044/month
Calendar Updated Nov 20 2009

Property Review

This experience was amazing for us. The condo made our experience the best because it was so clean and comfy. It was a nice place to know we could come back to after exploring all that the keys...
compare

Truman Annex - Renovated with Private Garden - Discounted Mid Dec Rates!!!

— Property 151840
Florida Keys condo rental - Living Space
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, beach, downtown, garden
Rates - per property (USD)
$895 - $1,600/week
$2,600 - $5,400/month
Calendar Updated Nov 20 2009

Property Review

We have rented this unit for the last two years and will do so again in the future. It's always been clean and fresh when we arrive. The owner is extremely accommodating and fun to talk to. The...
compare

OceanFRONT home new 2008, panoramic ocean views, pool, beach, WIFI - see Reviews

— Property 186650
Florida Keys house rental - View of Atlantic from deck of this oceanfront home
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, beach, waterfront, pool
Rates - per property (USD)
$1,990 - $3,050/week
Calendar Updated Nov 21 2009

Property Review

Dear Pat & Steve, We had a great week! The lobstering was great and the fishing was fun! We took home fresh lobster, tuna, and dolphin. Your views from the home were beautiful & we loved...
compare

Ocean Side Waterfront Home - Pool , Tennis, Fishing

— Property 317767
Florida Keys house rental - 'Villa Sombrero'
4 Bedrooms, Sleeps 10,
House, 4 Bathrooms, near the ocean, waterfront, pool
Rates - per property (USD)
$2,650 - $3,250/week
Calendar Updated Nov 20 2009

Property Review

Our family has been staying at this home every September for the past several years and we love it! The seawall is a magnificant place to watch the colorful sunsets; not to mention the great...
compare

'OLD TOWN OASIS' @ Truman Annex: Spacious 2 BR Oceanfront Condo

— Property 181289
Florida Keys condo rental - The Living Room- 10 ft ceilings & 50' high-def TV.
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, downtown, waterfront, balcony
Rates - per property (USD)
$2,400 - $3,950/week
$8,000 - $9,900/month
Calendar Updated Nov 22 2009

Property Review

The property at Truman Annex was exactly what we were looking for in a vacation property. The condo is in a great location, clean, bright, and well-maintained. The property manager was friendly...
compare

'CONCH CASA GRANDE' @ Truman Annex: 11' Ceilings, Private Pool & 6 Master Suites

— Property 177191
Florida Keys house rental - Conch Casa Grande: NOT your everyday 'conch home'.
7 Bedrooms, Sleeps 12,
House, 7 Bathrooms, downtown, near the ocean, balcony
Rates - per property (USD)
$7,000 - $15,000/week
$21,500 - $38,000/month
compare

'HIDDEN TREASURE' @ Casa East: Luxury 3BR's, Baby Grand Piano, Huge Private Pool

— Property 177317
Florida Keys house rental - The Living Room: big, breezy & comfortable...
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$6,600 - $11,000/month
compare

'COLORFUL CONCH' @ the Sanctuary: Decorator Home with 4BR/3BA & Private Pool

— Property 189356
Florida Keys house rental - Meticulously furnished to a very high standard...
4 Bedrooms, Sleeps 6,
House, 3 Bathrooms, beach, resort
Rates - per property (USD)
$6,600 - $11,000/month
compare

'SOUTHERN STAR' @ William Street: Luxurious 3BR/3BA Historic Old Town Home

— Property 193075
Florida Keys house rental - A very private yard & a gorgeous pool....
3 Bedrooms, Sleeps 6,
House, 3 Bathrooms, village, waterfront, pool
Rates - per property (USD)
$7,700 - $13,000/month
compare

“SOUTHWINDS” @ Key West Beach Club: 2 BR Beachfront Condo, Panoramic Ocean Views

— Property 204250
Florida Keys condo rental - Your balcony view speaks for itself...
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$6,600 - $9,900/month
compare

“PENNY'S POMPEI” @ Key West Golf Club: Elegant 2BR/1.5BA Townhome

— Property 229104
Florida Keys house rental - The living room: big flat screen TV & a sleep sofa
2 Bedrooms, Sleeps 6,
House, 1 Bathroom, 1 Half Bath, near the ocean, resort, pool
Rates - per property (USD)
$3,000 - $4,800/month
compare

'TURTLE CAY SPA' @ the Sanctuary: Walled Yard & 2 Master Suites

— Property 226088
Florida Keys house rental - Living room: large & airy with overhead fans
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, near the ocean, resort, pool
Rates - per property (USD)
$3,950 - $6,600/month
compare

'WATER'S EDGE' @ Gulfview Pointe: Luxurious 4BR Home on Florida Bay

— Property 230758
Florida Keys house rental - Water's Edge: on a quiet lane set in the mangroves
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, 1 Half Bath, near the ocean, waterfront, pool
Rates - per property (USD)
$6,600 - $14,000/month
Calendar Updated Nov 20 2009

Property Review

The Watersedge property was exactly as it was described but only better.We had a large group of people for my husbands 50th birthday and it was more than comfortable The home is located close to...
compare

'AZURE MORNING' @ Kings Pointe: Luxurious 3 Bedroom Condo on the Atlantic

— Property 202314
Florida Keys condo rental - The Balcony: dramatic views of the ocean
3 Bedrooms, Sleeps 8,
Condo, near the ocean, waterfront, pool
Rates - per property (USD)
$1,600 - $3,300/week
$4,800 - $7,700/month
Calendar Updated Nov 20 2009

Property Review

The location was just outside of Key West, which was perfect as it was close enough to enjoy down town, but away enough for peaceful evenings. My husband like the location because it was very...
compare

“HEAVENLY ZEN @ GRINNELL”: 4BR Private Home @ The Historic Seaport

— Property 238200
Florida Keys house rental - The courtyard is a peaceful oasis...
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, downtown, resort, pool
Rates - per property (USD)
$7,700 - $14,000/month
compare

“SOUTHERNMOST ARTS & CRAFTS”, 2BR/2BA Private Home @ South Street

— Property 238081
Florida Keys house rental - The Pool Area is truly an oasis
2 Bedrooms, Sleeps 6,
House, 2 Bathrooms, downtown, near the ocean, pool
Rates - per property (USD)
$6,000 - $9,000/month
compare

“NINA'S PENTHOUSE on the BEACH” 3BR/3BA 2-Story Condo @ The Key West Beach Club

— Property 238333
Florida Keys condo rental - You'll be able to watch both sunrises & sunsets.
3 Bedrooms, Sleeps 8,
Condo, 3 Bathrooms, beach, resort, pool
Rates - per property (USD)
$6,000 - $12,000/month
Calendar Updated Nov 20 2009

Property Review

You can't go wrong with Nina's penthouse, especially if you can enjoy the 3 full bedrooms and baths, two of which are well situated for privacy. The third bedroom is actually a suite with TV and...