Montgomery Cottages - Vacation Rentals in Lower Florida Keys

Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Artist House Key West From US $136
         

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9.8 (444 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Designated Smoking Area
  • TV
Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,150
         

9.8 (143 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Conch style home in Oldtown with private pool AND dock! From US $1,175
         

Luxury Places to Stay in Lower Florida Keys

Over 6356+ Luxury Places to Stay in or Near Lower Florida Keys

Top-Rated Vacation Rentals with a Pool in Lower Florida Keys

Over 4422+ Top-Rated Vacation Rentals with a Pool in or Near Lower Florida Keys
Almond Tree Inn Hotel - Adults Only From US $287
         

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10.0 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath From US $655
         

Everything Key West has to offer @ Mango Cottage From US $661
         

Key West Rooster From US $395
         

10.0 (176 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Lower Florida Keys

Over 2177+ Pet-Friendly Vacation Rentals in or Near Lower Florida Keys
Sunshine Key King Travel Trailer 4 From US $238
         

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8.9 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Old Wooden Bridge Resort and Marina From US $275
         

8.6 (349 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Oceanfront Cottage with dockage, pool just minutes to Key West! From US $218
         

Large Vacation Homes & Villas in Lower Florida Keys

Over 702+ Large Vacation Homes & Villas in or Near Lower Florida Keys
Pelico Paradise From US $304
         

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9.6 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Frigate's Nest in Little Torch From US $2,126
         

8.0 (4 Reviews)
House
  • Air Conditioner
  • Pool
  • TV

Wheelchair Accessible Vacation Homes in Lower Florida Keys

Over 1156+ Wheelchair Accessible Vacation Homes in or Near Lower Florida Keys
Point Break Suites From US $225
         

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7.3 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Weatherstation Inn From US $201
         

9.4 (1005 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Tropical Executive at The Truman Annex in Key West From US $449
         

GATED OCEANFRONT CONDO AT SMATHER'S BEACH From US $501
         

9.2 (150 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Steps To The Beach And The Sunrise From US $243
         

9.4 (118 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Lower Florida Keys Vacation Rentals and Airbnb Places to Stay Under $200

Over 559+ Lower Florida Keys Vacation Rentals and Airbnb Places to Stay Under $200
Blue Heaven at The Truman Annex in Key West From US $192
         

9.0 (51 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
The Grand Guesthouse From US $160
         

9.6 (1005 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Alhambra at The Truman Annex in Key West From US $159
         

8.6 (63 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
AQUA OASIS at The Truman Annex in Key West From US $192
         

9.4 (36 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Marlin Blue at the Truman Annex in Key West From US $159
         

9.8 (35 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Green Spot at The Truman Annex in Key West From US $192
         

9.4 (28 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Lower Florida Keys

Over 4060+ Instantly Bookable Vacation Homes in or Near Lower Florida Keys
Parking, Heated Pool, Pet Friendly - Seagate House From US $1,797
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Unique Home with loft @ Truman Annex From US $286
         

9.8 (119 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About Lower Florida Keys Vacation Rentals

With more than 6365 Lower Florida Keys vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Lower Florida Keys.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Lower Florida Keys, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Lower Florida Keys. Places to stay near Lower Florida Keys are 780.12 ft² on average, with prices averaging US $678 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Lower Florida Keys with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Lower Florida Keys

Type Count
Vacation Homes 3635
Holiday Apartments 626
Hotels 409
Resorts 251
Cottages 185
Villas 58
B&B 52
Cabin Rentals 14
Others 5
Hostels 2

Use these Quick Filters to Find a Vacation Rental in Lower Florida Keys

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Lower Florida Keys.

Weather in Lower Florida Keys

View the weather forecast for Lower Florida Keys before booking your Lower Florida Keys Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Lower Florida Keys Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Lower Florida Keys?
How many vacation rentals are available in Lower Florida Keys?

Currently, the total number of properties listed in 2026 is over 6365 in the Lower Florida Keys area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Lower Florida Keys.