Florida Keys Condo Rentals

Florida Keys Vacation Condos

Florida Keys condo rentals offer a relaxed, low-maintenance way to enjoy island living, with the comfort of home and the convenience of thoughtful amenities. Whether you are planning a couples trip, family vacation, group getaway, or longer island stay, condos can make it easy to settle in and enjoy the Keys without the upkeep of a larger private home.

Rental Style

Condos & Waterfront Stays

Best For

Couples, Families & Groups

Popular Areas

Key Largo to Key West

Top Features

Pools, Docks & Water Views

Florida Keys condo rentals are not one-size-fits-all. Some offer waterfront or canal-front views, some are located at marina communities, some include boat dock access, and a few may even feature a private pool. Options can range from cozy island condos to larger multi-bedroom layouts, including rentals with up to four bedrooms for families and groups.

  • Great option for couples, families, groups, and extended stays
  • Some condos offer waterfront, canal-front, or marina settings
  • Select rentals may include boat dock access or private pool features
  • Many include kitchens, living areas, balconies, parking, and easy access to local attractions
  • Available across Key Largo, Islamorada, Marathon, the Lower Keys, and Key West

Browse available condo rentals below, or explore nearby options like Florida Keys oceanfront rentals, homes with private pools, and vacation rentals with boat docks.

Florida Keys condo rental with pool, tropical landscaping, and island vacation setting

Rental Highlight

Easy island stays with flexible layouts, water views, pools, docks, and convenient amenities.


Properties Available 70 properties available
Welcome to Ohana Keys, a bright and inviting townhome in the sought-after Kawama Yacht Club in Key Largo, where island adventures, resort-style amenities, and laid-back Florida Keys living come together.Whether you're here to relax by the pool, spend the day on the water, or explore the Keys, Ohana Keys gives you the perfect home base for your
KL201 - Ohana Keys Rating 5 (10)
Condo
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 2 baths
In the heart of Old Town and just two steps up to enter, this charming single-story cottage is the perfect setting for your next getaway with family or friends. This snowbird-friendly condo boasts an unbeatable location within walking distance of lively Duval Street, fantastic local restaurants, Higgs Beach (with volleyball and tennis courts), a dr
28-night minimum 28-night minimum
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Dog Friendly Dog Friendly
This canal-front Keys charmer is your ticket to paradise! Along with scenic water views and direct access for kayaking or stand-up paddleboarding, you'll also enjoy membership privileges at the Cabana Club (across the street) featuring an oceanfront pool, a sandy beach area, and a snack bar. Public tennis courts and family facilities at First S
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

7-night minimum 7-night minimum
KC203A - Canalside at KCB Rating 5 (59)
Canalfront
- Key Colony Beach
Bedrooms 2 bedrooms
Bathrooms 3 baths
Welcome to 107 Coastal Vibes, a beautifully updated and fully furnished corner residence offering a bright, breezy coastal atmosphere with peek-a-boo views of the Atlantic Ocean. This charming condo features a spacious primary suite with king bed accommodations and a newly updated bathroom, while the light-filled living area flows seamlessly to a p
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

7-night minimum 7-night minimum
Canalfront
- Marathon
Bedrooms 1 bedroom
Bathrooms 1 bath
Half Baths 1 half bath
Welcome to your tropical escape in the heart of the Florida Keys!Leave the everyday behind and settle into island time at this beautifully appointed retreat, where sunshine, adventure, and relaxation await. Whether you're looking for a peaceful getaway or an action-packed vacation, this is the perfect home base for experiencing all that the Flo
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

7-night minimum 7-night minimum
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths
Welcome to Casa Del Soul, a colorful and effortless island stay! From the moment you step in the front door, you will take notice of the open-concept layout, bohemian furnishings, and lovely tropical theme. The living room's oversized sofa and large Smart TV offer the perfect combination for family hangouts. The adjacent full kitchen boasts a t
28-night minimum 28-night minimum
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Stunning, renovated condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed. Located on the eastern side of the island, this condo is part of the luxurious Sunrise Suites Resort. W
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
The ideal location of this super-comfortable corner property makes it the perfect blend of convenience, tranquility, and tropical Key West scenery. Sit back and relax as you sip cocktails on the balcony, prepare a light meal in the newly renovated kitchen, and unwind in front of the living room smart TV after a day at neighboring Fort Zachary Beach
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

28-night minimum 28-night minimum
KW245WK - Shipyard Seaclusion Rating 5 (145)
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Sun‑soaked days and cool ocean breezes await you at this oceanfront Key Largo retreat. With sweeping ocean views and shared amenities such as a pool, on‑site tennis, and private beach access, you'll find that fun and relaxation are always within reach.Just steps from the gently rolling waves and a little over seven miles from the heart of the i
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

Oceanfront
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 2 baths
This charming coastal retreat is the perfect hideout for a weekend at the pool or a quick trip to the beach. Within a five-mile radius of this cozy beachside cottage, you’ll find attractions such as Florida Keys Aquarium Encounters, Key Colony Beach Golf, and Sunset Park. Spend a day learning to snorkel the reefs, investigate the aquarium tou
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

7-night minimum 7-night minimum
Condo
- Marathon
Bathrooms 1 bath
Experience the very best of Key West living at this unique Old Town Truman Avenue Eyebrow home. Tucked away in a small, gated community, this luxury two-bedroom retreat showcases tranquil tropical decor and comes well-appointed with all the modern essentials of home. Whether you're visiting with the kids or sneaking away for a romantic couple&#
7-night minimum 7-night minimum
KW335WK - Dancing Palms Rating 5 (29)
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Slip into island time at this one-bedroom, one-bath condo for four in Key West, where you'll have entertainment and nearby beach access in an awesome central location. Sitting right downtown on Simonton Street, you're one street over from all the restaurants and bars on Duval, and within easy walking or biking distance from all the main att
Specials Tag View Special
Fall & Holiday Savings – Rates Reduced 15–20%!

Enjoy reduced rates for arrivals through December 31, 2026! Savings are already reflected in the rates shown online. No promo code needed!

KW31C - Jasmine Suite Rating 5 (309)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath

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