Islamorada, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Islamorada, Florida on RentalSaver.com!

Islamorada Rentals

From $387 per night (USD)
VRBO
Indulge in Home Like Comfort! Free Parking, Onsite Pool, Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $387 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $419 per night (USD)
VRBO
From $290 per night (USD)
VRBO
Charming 2/2 in Islamorada - Private Access to White Marlin Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This Islamorada house boasts 2 inviting bedrooms with 1 king bed and 2 queen beds. The spacious living room features a c ...
From $290 per night (USD)
VRBO
From $252 per night (USD)
Expedia
Charming 2-bedroom water-front home in Islamorada in the Florida Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Florida Keys are waiting for you at this 2-bedroom water-front home. Nestled in a tranquil setting, this quaint prop ...
From $252 per night (USD)
Expedia
From $297 per night (USD)
VRBO
Charming 3-bedroom townhome in fabulous Islamorada seconds from the bay!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your home away from home in Islamorada with 3 bedrooms plus a loft. This cool townhome features a king bed, queen bed, 2 ...
From $297 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Charming 3-bedroom condo with WiFi and AC in delightful Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience Islamorada like a local in this 3-bedroom condo. This superb property features 2 queen beds and 2 bunk beds, ...
From $295 per night (USD)
Expedia
From $867 per night (USD)
VRBO
Spacious & Remodeled condo w/ sunset views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LIVE AND LOVE THE FLORIDA KEYS LIFESTYLE! Welcome to this stunning, fully remodeled condo in the highly sought-after Fu ...
From $867 per night (USD)
VRBO
From $300 per night (USD)
Expedia
BAY UNIT! 3-bedroom townhome in beautiful Islamorada with full amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stunning Bay-View Townhome in Executive Bay Club – Newly Renovated! Don't miss out on this rare gem! Perfectly located ...
From $300 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Peaceful Retreat in Islamorada! Pet-friendly, Swimming Pool, Free Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $577 per night (USD)
VRBO
From $357 per night (USD)
VRBO
Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $357 per night (USD)
VRBO
From $322 per night (USD)
VRBO
Cozy waterfront home with dock, BBQ, dog friendly, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treasure Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $322 per night (USD)
VRBO
From $373 per night (USD)
Expedia
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience paradise like a local in this superb 2-bedroom 2 bath Villa with private patio and your own on premises boat ...
From $373 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Deep Water Home located in White Marlin Beach Neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036 LOCATION: Bayside Canal home located in the popula ...
From $319 per night (USD)
VRBO
From $3727 per night (USD)
VRBO
PRIVATE BEACH, Pickleball Court and Tiki Bar/ Heated Pool / Designated Paradise Key
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an ex ...
From $3727 per night (USD)
VRBO
From $786 per night (USD)
VRBO
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $786 per night (USD)
VRBO
From $1351 per night (USD)
Expedia
Beach Residence / Private overwater dock / Heated Pool / Mahi Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges ...
From $1351 per night (USD)
Expedia
From $733 per night (USD)
VRBO
Beautiful Beach House directly ON the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Islamorada Oceanfront home located directly on a private beach; enjoy swimming snorkeling, and ideal for kitesurfing! ...
From $733 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Come relax in this oceanside 2 bedroom home, in a pet friendly resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This home has amazing views of the Atlantic, and has 2 two bedroom, two baths. The vibe is tasteful and relaxing - jus ...
From $280 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Charming 2-bedroom house in brilliant Tavernier near Marinas and Founders Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Tavernier at this delightful house. This charming property features 2 bedrooms - one with a king bed and the o ...
From $235 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Ocean Resort, Key Largo
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to Paradise in Key Largo: Your Dream Vacation Awaits! Mile Marek 94.8 Welcome to your slice of paradise in Key ...
From $318 per night (USD)
Expedia
From $1301 per night (USD)
VRBO
Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
Indulge in the epitome of coastal living in these two connected expansive duplex penthouses boasting ocean views in Isla ...
From $1301 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Islamorada Tropical Paradise with New 40 Foot Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to your perfect getaway in beautiful Tavernier! This stunning vacation home offers the ultimate Florida Keys exp ...
From $237 per night (USD)
Expedia
From $578 per night (USD)
VRBO
Perfect Vacation home, heated/chilled pool, lots of dockage, private beach!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This fabulous house in Islamorada offers 5 bedrooms and 3 full bathrooms, heated/chilled pool, commerce ice machine, and ...
From $578 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Oceanview Studio Sleeps 3, Islamorada
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Nestled on the second floor with breathtaking ocean views, this studio is the perfect retreat for a cozy getaway in the ...
From $351 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Second Floor Den Suite Sleeps 6 Marina Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
This one-bedroom den suite in beautiful Islamorada offers the perfect blend of comfort and adventure. It has one queen b ...
From $396 per night (USD)
VRBO
From $303 per night (USD)
Expedia
Studio Escape at Caloosa Cove, Islamorada
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Embrace island life in the heart of the Florida Keys! Relax on the private beach or rent a charter for world-famous spor ...
From $303 per night (USD)
Expedia
From $1070 per night (USD)
VRBO
Minutes to Library Beach Park! 2 Villa w/ Living Area | Free Onsite Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Start with your ultimate bayside getaway, located along the stunning coastline. Our idyllic resort offers a tranquil esc ...
From $1070 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Beachfront Villa w/ Pier & Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to a tropical paradise at this villa at Topsider Resort in Islamorada. Nestled among lush gardens, this private o ...
From $287 per night (USD)
Expedia
From $660 per night (USD)
VRBO
Waterfront / Covered alfresco lounge / Heated Pool / Anchor Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This waterfront retreat, crafted for the ultimate outdoor lifestyle, features an expansive covered alfresco lounge with ...
From $660 per night (USD)
VRBO
From $100 per night (USD)
Expedia
Turnkey Modern Studio in the Upper Keys – Stylish, Bright & Fully Equipped!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gorgeous Turnkey Studio with Modern Finishes and Full Kitchen! Step into this beautifully updated, open-concept studio t ...
From $100 per night (USD)
Expedia
From $501 per night (USD)
VRBO
Waterfront / Ocean Access Canal / Kamp Key / Homes
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-con ...
From $501 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Fun Under the Sun! Beachfront, w/ Pool Onsite, Free Parking, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 370 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $428 per night (USD)
VRBO
From $705 per night (USD)
VRBO
Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony!
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
✦ Each room is 1350 sq. ft, equipped with complimentary toiletries, TV. ✦ Daily cleaning services included in the night ...
From $705 per night (USD)
VRBO
From $692 per night (USD)
VRBO
Island Living! Pool, Spa, 100’ Dock + Paddleboards – Islamorada Gem
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine w ...
From $692 per night (USD)
VRBO
From $619 per night (USD)
VRBO
2 Bedroom Updated Canal Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Your Dream Florida Keys Escape! This charming retreat offers modern upgrades, blending comfort and style, wit ...
From $619 per night (USD)
VRBO
From $1091 per night (USD)
VRBO
Waterfront Getaway in Venetian Shores – Pool, Hot Tub, Tiki Hut & More
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Located in the highly sought-after neighborhood of Venetian Shores, this spacious 5-bedroom, 3-bathroom home offers the ...
From $1091 per night (USD)
VRBO
From $641 per night (USD)
VRBO
Reel Paradise, Islamorada
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Mile Marker 74 – Bayside, Canal front Canal-Front Retreat with Pool & Prime Dockage | Lower Matecumbe Key, Islamorada ...
From $641 per night (USD)
VRBO
From $152 per night (USD)
VRBO
Islamorada Haven -- FIshing, watersports, relaxation
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This beautiful Islamorada home has been newly renovated and ready for your Margaritaville vacation. Sitting on a major ...
From $152 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Bay Harbour 209C ~ Chic 3 Bed / 2.5 Bath Condo with Ocean Views in Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Pressure Drop! This beautiful ocean-view condo features three bedrooms and two full bathrooms, making it an ...
From $525 per night (USD)
VRBO
From $165 per night (USD)
VRBO
Coastal Getaway at Plantation by the Sea
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Last minute July booking now offered at $3495! Escape to Islamorada and enjoy the laid-back lifestyle of the Florida Key ...
From $165 per night (USD)
VRBO
From $437 per night (USD)
VRBO
Bayfront Bliss in Islamorada, Private Dock & Stunning Sunset Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your front-row seat to breathtaking bayfront sunsets in the Indian Waterways neighborhood of Plantation Key! ...
From $437 per night (USD)
VRBO
From $2171 per night (USD)
Expedia
NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
License # 204. | ** 3 payment schedule available** | No Pet Charges | No security deposit | SATURDAY TO SATURDAY ONLY ...
From $2171 per night (USD)
Expedia
From $753 per night (USD)
VRBO
Luxury Waterfront Escape- Brand New Home In Venetian Shores
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to 104 Leoni Drive, a stunning new home in the highly sought-after Venetian Shores neighborhood of Islamorada. T ...
From $753 per night (USD)
VRBO
From $363 per night (USD)
VRBO
Experience Waterfront Bliss at Futura Yacht Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your slice of paradise at Futura Yacht Club! This beautifully renovated 2-bedroom, 2-bathroom townhome offers ...
From $363 per night (USD)
VRBO
From $664 per night (USD)
VRBO
Maison 308 Seaside Cove
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to paradise at Maison Matecumbe in Islamorada! This beautiful 3-bedroom, 3-bathroom townhome offers an unforgett ...
From $664 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Pool Home in Venetian Shores
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Spacious, open layout designed for ultimate comfort and convenience. The fully equipped kitchen flows seamlessly into th ...
From $396 per night (USD)
Expedia
Click For Pricing
VRBO
Matecumbe Resort: Your Home Away From Home in the Florida Keys-1 Bedrm with View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience Islamorada like a local in this superb 1-bedroom resort. The cozy bedroom features a king bed for a restful n ...
Click For Pricing
VRBO
From $450 per night (USD)
VRBO
Gorgeous, pool canal front home!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to your own slice of paradise in this stunning canal-front vacation home in Tavernier, Florida. This 3-bedroom, 2 ...
From $450 per night (USD)
VRBO
From $974 per night (USD)
VRBO
Nautica - Monthly 4 BR home on bay in Islamorada - Upper Matecumbe Key
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Mile Marker 83 – Bayfront Unfortunately all rentals must start on the 1st of the month. Island Villa Rentals and Owner' ...
From $974 per night (USD)
VRBO
From $159 per night (USD)
VRBO
Stunning Studio Apartment Summer Sea Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Beautifully remodeled Studio with tropically décor, this 1st floor corner unit (steps required) has a private outdoor en ...
From $159 per night (USD)
VRBO
From $113 per night (USD)
VRBO
Charming 1 Bedroom Condo on Plantation Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Sit back and relax at Port o Palms. Experience the ultimate Florida Keys getaway at this light and bright one-bedroom, ...
From $113 per night (USD)
VRBO
From $2378 per night (USD)
VRBO
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. T ...
From $2378 per night (USD)
VRBO
From $3276 per night (USD)
VRBO
Voted best boutique resort in Islamorada! Beach, dockage, pool + more!
Bedrooms:
7
Bathrooms:
8
Sleeps:
22
Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secu ...
From $3276 per night (USD)
VRBO
From $1718 per night (USD)
VRBO
Your Ultimate Keys Getaway Awaits!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroo ...
From $1718 per night (USD)
VRBO
From $346 per night (USD)
VRBO
Newly Renovated - 2-bedroom state of the art condo Islamorada. Perfect Location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Palms - Islamorada Brand New - Ripped down to the studs and just completed a $150k remodel with state of the art eve ...
From $346 per night (USD)
VRBO
From $3185 per night (USD)
VRBO
Private 150 Ft Oceanfront 2.5 Acre Estate with Saltwater Pool, Spa, Dock
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Completely renovated and expanded to over 3,700 square feet. San Roc is a private ocean front home with spectacular vie ...
From $3185 per night (USD)
VRBO
$Tranquility Cove \nBeautiful Remodeled home in the heart of Islamorada.$
From $270 per night (USD)
VRBO
Tranquility Cove \nBeautiful Remodeled home in the heart of Islamorada.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space This beautiful newly remodeled (99%) Completed , modern home sits in the middle of great restaurants, t ...
From $270 per night (USD)
VRBO
From $131 per night (USD)
VRBO
Pool, Beach and Tennis Court! Fishing, swimming and relaxation!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Take it easy at this unique and tranquil getaway. Enjoy this well equipped 2 bedroom, 2 bath home. Enjoy beautiful suns ...
From $131 per night (USD)
VRBO
From $287 per night (USD)
VRBO
Islamorada Hidden Treasure
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy luxury in the Florida Keys in this private oasis at Coral Harbour. The property is equipped with a marina, fuel, ...
From $287 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere.
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
AVAILABLE CHRISTMAS & NEW YEARS! Beautiful updated house on dead-end road with pool and private beach access. Launch a k ...
From $382 per night (USD)
VRBO
Click For Pricing
VRBO
Bay view villa in Islamorada, palm trees, shade trees and two private porches
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unwind with a Bay view, approx. 1 hour from Miami airport. Access to mini beach, great sunsets and boat ramp, swimming ...
Click For Pricing
VRBO
From $1192 per night (USD)
VRBO
The Sailfish House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to the “Sailfish House” at Tarpon Point! Soak up the sun and take in the spectacular views at this opulent 4 be ...
From $1192 per night (USD)
VRBO
From $508 per night (USD)
VRBO
4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Island Villa Rental Properties offers Seas The Day in Islamorada, Florida Keys. Seas the Day is a fun, 4 bedroom house ...
From $508 per night (USD)
VRBO
From $843 per night (USD)
VRBO
Spectacular Coastal Paradise with outstanding outdoor living spaces
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Escape to the islands in your own private resort. This Florida Keys home feels like your own private tropical oasis loc ...
From $843 per night (USD)
VRBO
From $444 per night (USD)
VRBO
Beautiful Keys Style Retreat - with bonus room, private pool and private dock.
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Experience paradise in our stunning 2-story, 2-bedroom, 3-bathroom rental property located in a peaceful residential nei ...
From $444 per night (USD)
VRBO
From $614 per night (USD)
VRBO
Venetian Shores 20K boat lift 28 day Minimum, ..August Cancellation now open....
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Venetian shores 4 bedroom 3 bath, pool, hotub, 300lbs ice machine with 20K boat lift, Master has a double walk-in shower ...
From $614 per night (USD)
VRBO
From $206 per night (USD)
VRBO
Beautiful 2 Bedroom 2 Bath Condo Coral Harbour Islamorada - Marina, Pool, Gated
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This special place is close to everything, making it easy to plan your visit. Beautiful updated 2 bedroom 2 bath watervi ...
From $206 per night (USD)
VRBO
Click For Pricing
Expedia
A place in paradise!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This unique home gives you the quintessential keys experience. Nestled in a small, quaint gated, private community with ...
Click For Pricing
Expedia
Click For Pricing
VRBO
PARADISE FOUND! 3 BD townhome in BEACHFRONT Executive Bay Club in Islamorada, FL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Paradise Found! Enjoy fantastic sunsets in an updated 1400 sq. ft. townhouse in beautiful Executive Bay Club, on mile ma ...
Click For Pricing
VRBO
From $448 per night (USD)
VRBO
Port Antigua Waterfront Home With Private Beach Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This Keys Home is Located in Beautiful Port Antigua. 4 Br/ 3 Ba Sleeps 8 Comfortably. All Rooms Have Queen Sized Beds. L ...
From $448 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Islamorada’s Finest Oceanfront Gated Community Soak up the sun and enjoy the ocean breeze from this charming ...
From $390 per night (USD)
VRBO
From $771 per night (USD)
Expedia
ISLAMORADA DREAM HOUSE
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
ONE-OF-A-KIND VACATION EXPERIENCE. You will never want to leave. Large open space, dining, kitchen and living room. Priv ...
From $771 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Zesty Lower Matecumbe Condo with Private Beach & Dockage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
It's not every day that you come across a rental like this. This delightful and fun 2 bedroom, 1.5 located in Lower Mate ...
From $194 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, w ...
From $447 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Mercy’s waterfront piece of paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our home is a unique place situated in the best location in the mid/upper keys. A single family property, all refurbishe ...
From $222 per night (USD)
VRBO
From $1074 per night (USD)
Expedia
The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Take your heart, family & fishing gear to the blissful Villa by the Bay! Quaint gated 8 homes; Coral Cove is centrally l ...
From $1074 per night (USD)
Expedia
From $399 per night (USD)
VRBO
The Nest Villa & Marina with boat ramp, sun terrace, water views & pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The "Nest" villa is one of only seven units nestled on a one acre native tropical hammock directly on Florida Bay with s ...
From $399 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Light + Bright Islamorada Pool Home with Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Islamorada Reef Home, a light and bright Islamorada pool home with dockage. You’ll feel right at home in th ...
From $461 per night (USD)
VRBO
From $516 per night (USD)
VRBO
Feel the breeze of the keys
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME** Perfect Vacation Home in Islamorada, the center of the Keys Island. T ...
From $516 per night (USD)
VRBO
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Expedia
Pristine canal-front home with heated pool and access to open water
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Beautifully appointed getaway perfectly situated to allow exploration of the mangroves or the open water, since Tavernie ...
Click For Pricing
Expedia
From $603 per night (USD)
VRBO
Immaculate Islamorada Home with 100' of Dockage, Pool & More!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This tropical oasis has everything you need and more for the perfect summer vacation! Nestled in the highly sought-aft ...
From $603 per night (USD)
VRBO
From $178 per night (USD)
VRBO
OCEAN FRONT TOWN HOUSE with breath taking views from all 3 balconies.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are delighted to offer this 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! Breathtaking views off of all 3 balco ...
From $178 per night (USD)
VRBO
From $870 per night (USD)
VRBO
Maison Matecumbe.... the heart of Islamorada!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Maison Matecumbe #301 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centra ...
From $870 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Tropical Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat ...
From $272 per night (USD)
Expedia
From $438 per night (USD)
VRBO
Pet Friendly 2 Bedroom in Venetian Shores Sleeps 10
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast ac ...
From $438 per night (USD)
VRBO
From $689 per night (USD)
VRBO
Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Minimum 28 day stay. Dreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in yo ...
From $689 per night (USD)
VRBO
From $775 per night (USD)
VRBO
Islamorada paradise vacation home in sought after Venation shores
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Location, location! Venetian Shores is the premier luxury private community with deep water access to Snake creek, which ...
From $775 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Canal-Front Florida Keys Home w/ Dock!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Ocean breezes and beautiful water views are in store at this 2-bedroom, 2-bathroom home. This Florida Keys vacation rent ...
From $264 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $314 per night (USD)
VRBO
From $314 per night (USD)
VRBO
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $314 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $261 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $261 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Ideal Location! Onsite Pool, Free Breakfast, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $261 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Trendy canal-front home with dock, full kitchen, central AC, & washer/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Salt House Swank Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $172 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Enjoy the good life in the perfect Islamorada Home!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
133 Stromboli Drive - If ever you have imagined yourself vacationing in Islamorada, this home was in your head! Beautif ...
From $515 per night (USD)
VRBO
From $206 per night (USD)
Expedia
Reel Paradise at Sea Gulls
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Stunning ocean views and beautiful island sunrises! The Space: Welcome to Reel Paradise! This beautiful condo ...
From $206 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Get ready to dive into your Islamorada Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
134 Tequesta Street - Get ready to dive into your Islamorada Winter Retreat! Move in ready today! This beautiful three-b ...
From $381 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Eclectic Easeful Stay At The Keys!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The buil ...
From $192 per night (USD)
Expedia
From $420 per night (USD)
VRBO
ENDLESS SUMMER- Ocean side, private pool, pet friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Pet friendly! Bring your boat and enjoy this large, 2-story house right on the ocean side. Private extra-large pool, Tik ...
From $420 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $274 per night (USD)
VRBO

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