Islamorada Rentals
From $1049 per night (USD)VRBO
Private Beachfront Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Village of Islamorada - Vacation Rental License No. 24-0248 This home is remodeled every year in some way or form...We ...
From $1049 per night (USD)VRBO
From $354 per night (USD)Expedia
A 57-foot trawler in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Located in a friendly marina with a restaurants, gift shop, tiki bar, kayaks, jet skis, and charter fishing boats minute ...
From $354 per night (USD)Expedia
From $543 per night (USD)VRBO
Boat, Fish, Swim from Your Own 70' Dock!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing und ...
From $543 per night (USD)VRBO
From $1348 per night (USD)Expedia
Hidden Gem Duplex in Heart of Islamorada! Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This truly is a Hidden Gem in the heart of Islamorada. Nestled in the trees just a few steps from one of the mo ...
From $1348 per night (USD)Expedia
From $148 per night (USD)VRBO
Beautiful 1 bedroom apartment with stunning open water view Apt 317
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Premier 1 bedroom unit with both that stunning direct open water bay view and a view of the pool off the balcony. Beauti ...
From $148 per night (USD)VRBO
From $1373 per night (USD)VRBO
Deep Blue Vacation Oceanfront Estate, Millionaire's Row, Private Saltwater Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Deep Blue Vacation Rental - Beautiful Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. ...
From $1373 per night (USD)VRBO
From $343 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 $343 per night (USD)VRBO
From $220 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 $220 per night (USD)VRBO
From $880 per night (USD)VRBO
Waterfront Home, Large Pool w Boat lift, Floating Dock, and Putting Green
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Custom waterfront home with large heated/chilled pool. 2 large docks with amazing water views. Located in the heart of T ...
From $880 per night (USD)VRBO
From $347 per night (USD)VRBO
Your Islamorada Vacation dream just became a reality!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
139 Venetian Way - Your Islamorada Winter Vacation dream just became a reality! Brand new to the market, this Venetian S ...
From $347 per night (USD)VRBO
From $267 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 $267 per night (USD)VRBO
From $513 per night (USD)VRBO
Private Cottage on Bayfront Estate – Pool, Beach, and Boating Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Garden View Cottage at Mermaid's Bay Boutique Estate, a serene hideaway located in the heart of Islamorad ...
From $513 per night (USD)VRBO
From $2598 per night (USD)VRBO
Oceanfront Estate with 4 Cozy Cottages
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 16
Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave o ...
From $2598 per night (USD)VRBO
From $991 per night (USD)VRBO
Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Bay View Cottage is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Isl ...
From $991 per night (USD)VRBO
From $145 per night (USD)VRBO
Modern one bedroom apartment with beautiful garden view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful, modern updated unit is absolutely beautiful with a private balcony with a wonderful garden view. Homey t ...
From $145 per night (USD)VRBO
From $436 per night (USD)VRBO
5 Star Modern Oceanfront Islamorada Townhome on the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Tw ...
From $436 per night (USD)VRBO
From $277 per night (USD)VRBO
Relaxing waterfront retreat with boat dock & amazing ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $277 per night (USD)VRBO
From $168 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 $168 per night (USD)VRBO
From $376 per night (USD)VRBO
Breezy Happy Hours in Port Antigua Beach Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $376 per night (USD)VRBO
From $283 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 $283 per night (USD)VRBO
From $212 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 $212 per night (USD)VRBO
From $220 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 $220 per night (USD)VRBO
From $205 per night (USD)VRBO
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 $205 per night (USD)VRBO
From $2853 per night (USD)VRBO
Open Ocean Views - 2 separate properties -House & Cottage With Dockage & Pool
- Bedrooms:
- 4
- 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 $2853 per night (USD)VRBO
From $415 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 $415 per night (USD)VRBO
From $875 per night (USD)VRBO
Bayfront Home In Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy your stay at your own private oasis! You will approach this stunning home down a secluded road that leads into pa ...
From $875 per night (USD)VRBO
From $2561 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 $2561 per night (USD)VRBO
From $682 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 $682 per night (USD)VRBO
From $468 per night (USD)VRBO
Clean, Fully Remodeled, stocked Houseboat, 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 $468 per night (USD)VRBO
From $1933 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 $1933 per night (USD)VRBO
From $1462 per night (USD)VRBO
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed\/5 bath with Den & Nursery
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Islamorada Rental License: VR - 065 *** SATURDAY TO SATURDAY RENTALS ONLY! *** Please note: VRBO is having some AI up ...
From $1462 per night (USD)VRBO
From $261 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 $261 per night (USD)VRBO
From $225 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 $225 per night (USD)VRBO
From $278 per night (USD)VRBO
Water Front 3\/3 Family and Boat Friendly Home, Great Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $278 per night (USD)VRBO
From $291 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 $291 per night (USD)VRBO
From $279 per night (USD)Expedia
3 Bedroom \/ 3 Bathroom Canal Front Home in Tavernier
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $279 per night (USD)Expedia
From $487 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 $487 per night (USD)VRBO
From $1113 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 $1113 per night (USD)Expedia
From $726 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 $726 per night (USD)VRBO
From $728 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 $728 per night (USD)VRBO
From $896 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 $896 per night (USD)VRBO
From $910 per night (USD)Expedia
3 Bedroom Private Oceanfront House - Sol
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overl ...
From $910 per night (USD)Expedia
From $306 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 $306 per night (USD)VRBO
From $711 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 $711 per night (USD)VRBO
From $715 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 $715 per night (USD)VRBO
From $412 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 $412 per night (USD)VRBO
From $763 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 $763 per night (USD)VRBO
From $1173 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 $1173 per night (USD)VRBO
From $587 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 $587 per night (USD)VRBO
From $763 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 $763 per night (USD)VRBO
From $498 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 $498 per night (USD)VRBO
From $704 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 $704 per night (USD)VRBO
From $1819 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 $1819 per night (USD)VRBO
From $780 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 $780 per night (USD)VRBO
From $792 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 $792 per night (USD)VRBO
From $763 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 $763 per night (USD)VRBO
From $1819 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 $1819 per night (USD)VRBO
From $679 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 $679 per night (USD)VRBO
From $763 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 $763 per night (USD)VRBO
From $646 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 $646 per night (USD)VRBO
From $152 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 $152 per night (USD)VRBO
From $2097 per night (USD)VRBO
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Spectacular property - two stories of true keys paradise in a relaxed basin-front setting. Newly renovated, the proper ...
From $2097 per night (USD)VRBO
From $550 per night (USD)VRBO
Cozy Cottage in the Heart of Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $550 per night (USD)VRBO
From $334 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 $334 per night (USD)VRBO
From $875 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 $875 per night (USD)VRBO
From $1032 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 $1032 per night (USD)VRBO
From $458 per night (USD)VRBO
A Piece of Paradise Islamorada, Fl. On the water 3\/2, 90 Ft of dock New Pool
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. T ...
From $458 per night (USD)VRBO
From $1924 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 $1924 per night (USD)VRBO
From $277 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 $277 per night (USD)VRBO
From $233 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 $233 per night (USD)VRBO
From $442 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 $442 per night (USD)VRBO
From $360 per night (USD)VRBO
Casa Mia 7862778706
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Absolutely comfortable keys Home , great location to restaurants and activities, two bedroom and two full bath upstairs ...
From $360 per night (USD)VRBO
From $9237 per night (USD)VRBO
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 $9237 per night (USD)VRBO
From $413 per night (USD)Expedia
💎AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM
- 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 $413 per night (USD)Expedia
From $292 per night (USD)VRBO
Tropical Escape | Sea Gulls 407 ~ Weekly Rental
- 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 $292 per night (USD)VRBO
From $2183 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 $2183 per night (USD)VRBO
From $170 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 $170 per night (USD)VRBO
From $1453 per night (USD)VRBO
Waterfront... 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 $1453 per night (USD)VRBO
From $158 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 $158 per night (USD)VRBO
From $398 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 $398 per night (USD)VRBO
From $889 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 $889 per night (USD)VRBO
From $567 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 $567 per night (USD)VRBO
From $197 per night (USD)VRBO
Oceanside townhome 2\/2 with boat ramp and dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful newly renovated townhouse is the prefect vacation home for you and your family. The third floor has a mas ...
From $197 per night (USD)VRBO
From $170 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 $170 per night (USD)VRBO
From $210 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 $210 per night (USD)VRBO
From $655 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 $655 per night (USD)VRBO
From $666 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 $666 per night (USD)VRBO
From $478 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 $478 per night (USD)VRBO
From $188 per night (USD)VRBO
Executive Bay - 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 $188 per night (USD)VRBO
From $389 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 $389 per night (USD)VRBO
From $1614 per night (USD)VRBO
Beautiful Oceanfront Oasis with Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Sea Ranch - Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marke ...
From $1614 per night (USD)VRBO
From $166 per night (USD)VRBO
Summer Special! Stunning 1st floor 2 bedroom Condo at Summer Sea
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Reduced price for summer of 2024. Summer Sea Condo #108: Newly remodeled and beautifully decorated 1st floor corner uni ...
From $166 per night (USD)VRBO
From $630 per night (USD)VRBO
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 $630 per night (USD)VRBO
From $450 per night (USD)Expedia
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 $450 per night (USD)Expedia
From $1824 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 $1824 per night (USD)VRBO
From $394 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 $394 per night (USD)VRBO
From $166 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 $166 per night (USD)VRBO
From $540 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 $540 per night (USD)VRBO
From $579 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 $579 per night (USD)VRBO
From $365 per night (USD)Expedia
Whispering Palms | Sea Gulls 210 ~ Weekly Rental
- 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 $365 per night (USD)Expedia