Islamorada Rentals
- From $113 per night (USD)
VRBO
End Unit Townhouse-Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
End Unit Townhouse in Beautiful Islamorada. Gated Community. Two bedrooms and 1 1/2 baths . One Bedroom has two queen be ...
From $113 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Canal Front Beautifully Renovated Home w\/ Great Deck, Private Boat Ramp + WI-FI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This comfortable house, located in the quiet neighborhood of Plantation Key Colony, Offers three inviting bedrooms and 2 ...
From $360 per night (USD)VRBO
- From $195 per night (USD)
VRBO
Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is located in your tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yac ...
From $195 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Beautiful water front home, private dock in Islamorada, World Fishing Capital
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
This two-story house is located on an ocean access canal that is literally minutes from the Atlantic Ocean. Guest can do ...
From $180 per night (USD)VRBO
- From $189 per night (USD)
VRBO
Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Watch the sunrise from your private balconies in both bedrooms overlooking the Atlantic ocean, and walk across the stree ...
From $189 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Off the beaten path in one of Islamorada’s hidden gem of a community!.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest nei ...
From $175 per night (USD)Expedia
- From $2514 per night (USD)
VRBO
Open Ocean Views - 2 separate properties -House & Cottage With Dockage & Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 4
We privately own a total of 5 boutique vacation rentals in Islamorada: VRBO listing #1576833 (5 bedroom) VRBO listing #1 ...
From $2514 per night (USD)VRBO
- From $288 per night (USD)
VRBO
Charming Islamorada waterfront home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
118 Sea Lane - Charming waterfront located on the oceanside 76-mile marker. Sea Lane offers immediate access to the Atla ...
From $288 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Islamorada's newest vacation rental address is YOURS!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
169 Sebring Drive - Tucked away in a quiet neighborhood with a gated homeowners park, Sebring Drive is located at the 89 ...
From $180 per night (USD)VRBO
- From $141 per night (USD)
VRBO
Beautiful 2 bedroom Summer Sea Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, modern, upgraded 2-bedroom, 1.5 bath apartment at Summer Sea has everything you would want for your fabu ...
From $141 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Breezy Happy Hours in Port Antigua Beach Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This 2,500sf home has been completely renovated. With 4/3.5 this comfortable home is located in one of the most desirabl ...
From $325 per night (USD)VRBO
- From $245 per night (USD)
VRBO
Tavernier Creek - Plantation Key Home - 60' Dockage May & September Available!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Port of Call." The only thing missing is You and Your Boat! And You are in the premier location, just off Ta ...
From $245 per night (USD)VRBO
- From $1821 per night (USD)
VRBO
Stunning Oceanfront Home located in Islamorada Florida
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning, completely renovated 5 bedroom, 6.5 bathroom home, sleeps 14 guests. Southwind sits on 1 acre of beachfr ...
From $1821 per night (USD)VRBO
- From $665 per night (USD)
VRBO
\" Endless Summer\" Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Stay in a beautiful home in one of the best communities in the Florida Keys, Venetian Shores. You can watch from your v ...
From $665 per night (USD)VRBO
- From $379 per night (USD)
VRBO
Clean Fully Remodeled House Boat w\/ Great Wifi! Luxury on the Water
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Very spacious, Comfortable and "super clean" Houseboat. “Baycation” is a 44'x15' triple level upper deck ...
From $379 per night (USD)VRBO
- From $1298 per night (USD)
VRBO
A brand-new luxury home built for relaxation with an astonishing outdoor space!
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 12
*** MINIMUM 28 NIGHT STAY *** Once you check-in, you’ll never want to leave 216 Johnny Road With quick ocean access, a ...
From $1298 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Islamorada beach house - PRIVATE BEACH - KAYAKS - DOCK SPACE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the Florida Keys from our newly renovated home in a quaint neighborhood located in Islamorada. This 2 bedroom, 2 ...
From $250 per night (USD)VRBO
- From $198 per night (USD)
VRBO
3 Bedroom \/ 3 Bathroom Canal Front Home in Tavernier
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful 3 bedroom 3 bathroom canal front home is truly the perfect piece of paradise. The home is located in the ...
From $198 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Lg Waterfront lot off Tavernier Crk. 26' dock space, 3\/3-two living areas, Grill
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The property has a huge corner lot with a double sliding gate ample room to keep your trailer and/or trailers as well a ...
From $450 per night (USD)VRBO
- From $928 per night (USD)
Expedia
4 Bedroom Private Oceanfront House - Bahia
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 4 bedroom private oceanfront house overl ...
From $928 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Wonderful Retreat at relaxing Paradise . Full house or downstairs apartment
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
MINIMUM STAY: 29 DAYS - Very comfortable 50ft wide canal home located in Islamorada close to Snake Creek Channel with ...
From $339 per night (USD)VRBO
- From $3000 per night (USD)
VRBO
Luxurious Oceanfront Estate with Private Beach, Pool, and Putting Green
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Tarpon Harbor is a gated, two-acre, ocean front estate located in the beautiful town of Tavernier near Islamorada, Flori ...
From $3000 per night (USD)VRBO
- From $1396 per night (USD)
VRBO
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Islamorada Rental License: VR - 065 *** Please note: VRBO is having some AI update issues with no date to resolve. Th ...
From $1396 per night (USD)VRBO
- From $320 per night (USD)
VRBO
3 Bed Beautiful Keys Home, Quick walk to private beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If you are looking for the perfect home base for your family gathering or friend getaway look no further than this quai ...
From $320 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Canalfront, Dog-Friendly Home with High-Speed WiFi, Private Boat Ramp, and Kayak
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Islamorada Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $153 per night (USD)VRBO
- From $308 per night (USD)
VRBO
Water Front 3\/3 Family and Boat Friendly Home, Great Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your famil ...
From $308 per night (USD)VRBO
- From $775 per night (USD)
VRBO
Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Happy Tarpon - the best of the Florida Keys and the best of Islamorada! Enjoy privacy in our beautifully renovated home ...
From $775 per night (USD)VRBO
- From $803 per night (USD)
Expedia
3 Bedroom Private Oceanfront House - Sol
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overl ...
From $803 per night (USD)Expedia
- From $575 per night (USD)
VRBO
Waterfront, Heated Pool, Spa & 15k lb Boat Lift: Express access to Ocean & Bay!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Fisherman's paradise! 70 feet of Canalfront with immediate access to ocean or bay and 15k pound boat lift. MINIMUM 28 N ...
From $575 per night (USD)VRBO
- From $995 per night (USD)
VRBO
Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
SANCTUARY FOUND… At the intersection of two very wide sparkling canals sits this lovely, four bedroom, two and a half ba ...
From $995 per night (USD)VRBO
- Click For Pricing
VRBO
Ocean Front Contemporary Beach House, Islamorada.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the sweet spot of the Florida Keys - Islamorada. Custom built and designed by an Award winning architect in 2 ...
Click For PricingVRBO
- From $375 per night (USD)
VRBO
Port Antigua Florida Keys, Islamorada, Waterfront, 4 Bdrm, 3 Bath, Dock, Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This is a beautiful, 3 story home with 4 bedrooms, which includes 2 master bedrooms and their own individual private bat ...
From $375 per night (USD)VRBO
- From $321 per night (USD)
VRBO
Penthouse Retreat with 360* view of Ocean\/Bay Rooftop Lounge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Islamorada Penthouse Condo - Beautifully furnished and Fantastic layout - living space is all on one level. Some ocean v ...
From $321 per night (USD)VRBO
- From $598 per night (USD)
VRBO
Oceanfront, Pool, Dock... Checks all the boxes!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
141 LeSerra Lane - Freewheeler Vacations newest weekly rental is now available for your next Islamorada Vacation! Locate ...
From $598 per night (USD)VRBO
- From $126 per night (USD)
VRBO
Charming 1 Bedroom Condo with Ocean Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SeaGulls #602 - This lovely one bedroom one bath condo is only about an hour and fifteen-minute drive from Miami Interna ...
From $126 per night (USD)VRBO
- From $786 per night (USD)
VRBO
The Beach House-Luxury Oceanfront Home, Views, Pool, Sandy Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
‘The Beach House’ at Tarpon Point in Islamorada-OWNER DIRECT RENTAL WITH NO ADDITIONAL FEES This end home offers privac ...
From $786 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Stunning Keys home w\/pool, jetted tub, elevator & more!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Paradise. Come and relax in our Bayside home and enjoy the coastal breeze and rustling palms in your own pri ...
From $350 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Large Caribbean-Style Home w\/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $678 per night (USD)VRBO
- From $1043 per night (USD)
VRBO
Beautifully Renovated Home w\/ Custom Furnishings, Chef's Kitchen, & Veranda
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. Every detail and fixture was handpi ...
From $1043 per night (USD)VRBO
- From $537 per night (USD)
VRBO
Oceanfront Home w\/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to The Bird of Paradise. This Oceanfront home has everything you need for a relaxing getaway. Custom High ceilin ...
From $537 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $678 per night (USD)VRBO
- From $470 per night (USD)
VRBO
Cozy Caribbean-Style Home w\/ Outdoor Veranda - Steps to Beach-Entry Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $470 per night (USD)VRBO
- From $626 per night (USD)
VRBO
Caribbean-Style Family Home w\/ Kitchen, WiFi, Outdoor Veranda, & Washer-Dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $626 per night (USD)VRBO
- From $1617 per night (USD)
VRBO
Custom-Built Oceanfront Caribbean Home w\/ Gorgeous Ocean & Sunrise Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Carib ...
From $1617 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Veranda, & Full Washer-Dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $678 per night (USD)VRBO
- From $865 per night (USD)
VRBO
Spacious Caribbean-Style Home w\/ Kitchen, WiFi, Grill, & Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $865 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Breezy Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $678 per night (USD)VRBO
- From $1617 per night (USD)
VRBO
Custom-Built Oceanfront Caribbean Home w\/ Incredible Ocean & Sunrise Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Carib ...
From $1617 per night (USD)VRBO
- From $596 per night (USD)
VRBO
Bright Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $596 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Veranda, & Washer-Dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $678 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Spacious Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $678 per night (USD)VRBO
- From $400 per night (USD)
VRBO
A Piece of Paradise Islamorada, Fl. On the water 3\/2, 90 Ft of dock New Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. T ...
From $400 per night (USD)VRBO
- From $1672 per night (USD)
VRBO
This is The Oasis, YOUR private Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Oasis - This majestic property is over 2.75 acres of landscaped beauty. There is more white sand on this lot than an ...
From $1672 per night (USD)VRBO
- From $1800 per night (USD)
VRBO
7 Bedroom with Dockage - Pool, Paddle Boards, Kayaks included
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
We privately own a total of 5 boutique vacation rentals in Islamorada: VRBO listing #1576833 (5 bedroom) VRBO listing #1 ...
From $1800 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Cozy Cottage in the Heart of Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Little Bay Cottage - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private ...
From $448 per night (USD)VRBO
- From $277 per night (USD)
VRBO
Expansive Ocean views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour K-35 - This newly renovated unit is located in Ocean Harbor, one of the most exclusive condominiums in Isl ...
From $277 per night (USD)VRBO
- From $746 per night (USD)
VRBO
Beautiful Maison #307
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Maison Matecumbe #307 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centra ...
From $746 per night (USD)VRBO
- From $1250 per night (USD)
VRBO
You will never want to leave
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Ocean Retreat offers breathtaking views from every room, with a 60' covered balcony that overlooks the 32' Pool/Spa ...
From $1250 per night (USD)VRBO
- From $231 per night (USD)
VRBO
Sunset from our own Private Balcony Directly over the Bay
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Paradise in the Upper Keys. Just under 1 1/2 hrs. from Miami you can rent a piece of Heaven this Winter Season. Prime co ...
From $231 per night (USD)VRBO
- From $378 per night (USD)
VRBO
Cute & Cozy 3 Bedroom Canalfront Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
137 Cortez Drive - The dream home away from home. The upstairs main floor offers two large bedrooms with cozy king beds, ...
From $378 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Casa Mia 7862778706
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Absolutely comfortable keys Home , great location to restaurants and activities, two bedroom and two full bath upstairs ...
From $261 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Your Keys Getaway - A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A beautiful home on the bay, in sunny Islamorada, Florida. You have access to one of the only beaches in Islamorada, whi ...
From $200 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Bougainvilleas Canal Front Home with Pool and Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom / 3 bath canal front home is located in one of Tavernier’s desirable neighborhoods. Come enjoy this fun ...
From $295 per night (USD)VRBO
- From $6678 per night (USD)
Expedia
Bay front 6BDr Private Beach Pickle-ball Ct Game-room+ Sunset Views
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This absolutely spectacular bayside estate is available for rentals to the public for the first time. Recently upgraded ...
From $6678 per night (USD)Expedia
- From $293 per night (USD)
VRBO
💎AQUAMARINE💎<-WALL 2 WALL-> OCEAN-VIEW🌊+DOCK+POOL+SPA+GYM+🎾+DEALS ⭐️⭐️⭐️⭐️⭐️
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
💎 PLEASE EMAIL US WITH ANY QUESTIONS??? WE ARE HAPPY TO PROVIDE THE ANSWERS ABOUT OUR PROPERTY, OUR RESORT, RESTAURANT ...
From $293 per night (USD)VRBO
- From $291 per night (USD)
Expedia
New Tropical Escape | Sea Gulls 407
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Located right on the Atlantic Ocean, in the heart of the Florida Keys on Plantation Key - the sport fishing and ...
From $291 per night (USD)Expedia
- From $1821 per night (USD)
VRBO
Private Tropical Oceanfront Estate with Pool and Beach
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Last Resort Too - Welcome to Last Resort Too. This private hidden gem is situated on two prime oceanfront acres with a s ...
From $1821 per night (USD)VRBO
- From $143 per night (USD)
VRBO
STUNNING CONDO with BALCONY\/POOL in Oceanfront Building in beautiful Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gorgeous 2 bedroom 2 bath condo all on one floor with HEATED POOL, DOCK FOR FISHING, AND OUTDOOR BALCONY. Gated commun ...
From $143 per night (USD)VRBO
- From $1261 per night (USD)
VRBO
NEW LISTING... The Sapodilla House... Islamorada Family Estate Home...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The Sapodilla House - The Sapodilla House is one of Islamorada’s gems. This tropical, sprawling estate has every amenity ...
From $1261 per night (USD)VRBO
- From $127 per night (USD)
VRBO
1B-Stunning Bay View from Every Window & Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summer Sea Condominium Unit 213 is a heavenly one bedroom, one bath apartment with an amazing direct bay view from the l ...
From $127 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Islamorada Spectacular Vacation At Executive Bay Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come, Enjoy and Relax in our beautiful piece of the paradise in the Florida Keys. The Executive Bay Club is located in I ...
From $175 per night (USD)VRBO
- From $253 per night (USD)
VRBO
Canal front 3BR\/3Bath home with quick access to Bay & Ocean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3BR/3 bath home in desirable Plantation Key. Private 1BR/1 bath downstairs with a queen bed. Upstairs is a Master BR/b ...
From $253 per night (USD)VRBO
- From $775 per night (USD)
VRBO
Ultimate luxury vacation home in Islamorada, Florida!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
SPECTACULAR HOME AND FISHERMAN'S PARADISE IN VENETIAN SHORES! This home is located in close proximity to many shopping ...
From $775 per night (USD)VRBO
- From $495 per night (USD)
VRBO
Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and priv ...
From $495 per night (USD)VRBO
- From $176 per night (USD)
VRBO
Oceanside townhome 2\/2 with boat ramp and dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful newly renovated townhouse is the prefect vacation home for you and your family. The third floor has a mas ...
From $176 per night (USD)VRBO
- From $141 per night (USD)
VRBO
Beautiful sunsets & water views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bayfront Sand Pebbles #304 - A desirable Islamorada condo complex with a total of only 16 units. This two-bedroom two ba ...
From $141 per night (USD)VRBO
- From $604 per night (USD)
VRBO
The PERFECT ESCAPE with Private Pool and Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful 4 bedroom/ 4 bathroom home has a 60' dock. Its canal leads straight out to Snake Creek and has immediate ...
From $604 per night (USD)VRBO
- From $523 per night (USD)
VRBO
Beautiful 3 Bedroom Condo - Bay Harbour A101
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour A-101 - Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 ...
From $523 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Breathtaking ocean views for your Paradise vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house s ...
From $400 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Executive Bay Club - Great Unit Next to Beach and Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come to Paradise and Enjoy it in comfort.! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), par ...
From $165 per night (USD)VRBO
- From $336 per night (USD)
VRBO
Great Townhome with Basin & Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Townhome #731 - Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a tw ...
From $336 per night (USD)VRBO
- From $1344 per night (USD)
VRBO
Beautiful Oceanfront Oasis with Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Sea Ranch - Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marke ...
From $1344 per night (USD)VRBO
- From $123 per night (USD)
VRBO
Stunning 1st floor 2 bedroom Condo at Summer Sea
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summer Sea Condo #108: Newly remodeled and beautifully decorated 1st floor corner unit with a private outdoor entrance ...
From $123 per night (USD)VRBO
- From $495 per night (USD)
Expedia
Bay Harbour Islamorada Oceanfront Views 3\/2.5 UPDATED condo DOCK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful views from this condo dock 32 available- Unit C109 License Number: VR-194 Bay Harbour is a gated community l ...
From $495 per night (USD)Expedia
- From $360 per night (USD)
VRBO
3200 square ft. Masterpiece Home Fishing Paradise Waterfront 4 \/ 3 Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
"Monthly rentals only, no split months, thank you." Day 1, of the month , to end of the month. Welcome, to GULFVIEW 150 ...
From $360 per night (USD)VRBO
- Click For Pricing
VRBO
4 Bedroom home w\/ pool, DOCKAGE, beach access & more in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Island Villa Rental Properties offers this large, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in ...
Click For PricingVRBO
- From $1686 per night (USD)
VRBO
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
We privately own a total of 5 boutique vacation rentals in Islamorada: VRBO listing #1576833 (5 bedroom) VRBO listing #1 ...
From $1686 per night (USD)VRBO
- From $314 per night (USD)
VRBO
Islamorada Bay Harbour 2\/2.5 Condo Free DOCK included -Rate Specials!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Unit B106 Village of Islamorada: License Number: 24-0368. Bay Harbour is a gated community located at MM 75 bayside i ...
From $314 per night (USD)VRBO
- From $133 per night (USD)
VRBO
Stunning 2-Bedroom with a million-dollar Bay View!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This Fantastic Condo is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacular sunsets and ...
From $133 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour A-304 – Beautiful three bedroom two and a half bath luxury penthouse condo located at mile marker 74.5 baysi ...
From $448 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Holly’s Hideout (Fisherman's Dream)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This amazing home is centrally located on a clean, clear canal with deep water access to either the bay or ocean via Tav ...
From $500 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Tropical Waterfront Paradise!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This charming home sits on a large tropical lot with a covered tiki and a hot tub for late afternoon relaxation. Venetia ...
From $550 per night (USD)VRBO
- From $331 per night (USD)
VRBO
Whispering Palms | Sea Gulls 210
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: A peaceful sweeping view of the Atlantic stretches the entire length of this oversized balcony. FULL OCEAN VIEW ...
From $331 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Tarpon Bend ocean view with boat lifts
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
3/2 Waterfront Home in Lower Matecumbe Key in Islamorada, Florida. Featuring a 70' ft private dock with 2 boatlifts (1- ...
From $325 per night (USD)Expedia
- From $899 per night (USD)
VRBO
Modern Keys Penthouse W\/ Private Beach & Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This brand new, three bedrooms, three-and-a-half-bathroom penthouse unit is located within a luxury beachfront ...
From $899 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Beautiful Home On The Bay
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Large Home on Florida Bay, wonderful sunsets, great fishing, diving, kayaking etc.. This home could accommodate two fam ...
From $650 per night (USD)VRBO
- From $296 per night (USD)
VRBO
3\/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay - this family favorite is just 67 miles south of Miami! ...
From $296 per night (USD)VRBO
- From $319 per night (USD)
VRBO
Beautiful 3 Bedroom Condo with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour K-21- Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from hom ...
From $319 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
VILLAGE. RENTAL LICENSE # VR-007 Please always send email request with dates desired , as sometimes the dates on the ca ...
From $395 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And ...
From $200 per night (USD)VRBO