Islamorada Rentals
From $672 per night (USD)VRBO
House with ocean and bay views in Middle Keys with boat launch, ramp and dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your perfect getaway in Islamorada/Lower Matecumbe. This charming rental home offers the best of both worlds ...
From $672 per night (USD)VRBO
From $282 per night (USD)Expedia
Charming Bayside 2 bed, 2 bath Condo at Futura in Islamorada WiFi, Pool, Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This charming and beautifully renovated 2 bedroom condo is located in the Futura Yacht Club community at mile marker 88. ...
From $282 per night (USD)Expedia
From $260 per night (USD)VRBO
Winter Escape, Modern 3-bedroom plus Loft, Heated Pool, Beach, Fishing Pier
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a warm winter in the Florida Keys at this beautifully furnished 3-bedroom, 2.5 bathroom townhouse with bonus loft ...
From $260 per night (USD)VRBO
From $542 per night (USD)Expedia
Pool Home in Venetian Shores
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Spacious, open layout designed for ultimate comfort and convenience. The fully equipped kitchen flows seamlessly into th ...
From $542 per night (USD)Expedia
From $3582 per night (USD)VRBO
PRIVATE BEACH / Pickleball Court and Tiki Bar / Heated Pool / Designated Paradise Key
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an ex ...
From $3582 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 $995 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 $995 per night (USD)VRBO
From $321 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 $321 per night (USD)VRBO
From $511 per night (USD)VRBO
Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Islamorada, this peaceful 2-bedroom house. Ocean front -Private beach is a welcoming retreat for guests. this ...
From $511 per night (USD)VRBO
From $272 per night (USD)Expedia
Wake up every day to the sunrise from the deck of this waterfront home 2bed home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely home has 2 bedrooms and 2 baths. The home is completely furnished, just bring you sunscreen, flip flops and ...
From $272 per night (USD)Expedia
From $204 per night (USD)VRBO
Quaint Islamorada Cottage with Unbeatable Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this quaint 2-bedroom, 1-bathroom conch-style cottage in the heart of Islamorada. The fully equipped kitchen a ...
From $204 per night (USD)VRBO
From $2213 per night (USD)Expedia
Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
License # 204. | ** 3 payment schedule available** | No Pet Charges | No security deposit | SATURDAY TO SATURDAY ONLY ...
From $2213 per night (USD)Expedia
From $789 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 $789 per night (USD)VRBO
From $963 per night (USD)Expedia
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $963 per night (USD)Expedia
From $1669 per night (USD)VRBO
Private Beach / Private overwater dock / Heated Pool / Mahi Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges ...
From $1669 per night (USD)VRBO
From $2522 per night (USD)Expedia
Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Indulge in the epitome of coastal living in these two connected expansive duplex penthouses boasting ocean views in Isla ...
From $2522 per night (USD)Expedia
From $279 per night (USD)VRBO
Relax in this oceanside, pet-friendly 2BR home! Min 28-Day Reservation Required
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This home has amazing views of the Atlantic and has two bedrooms and two baths. The vibe is tasteful and relaxing - jus ...
From $279 per night (USD)VRBO
From $195 per night (USD)Expedia
Charming 2-bedroom home in brilliant Tavernier near Marinas and Founders Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Tavernier at this delightful home. This charming property features 2 bedrooms - one with a king bed and the ot ...
From $195 per night (USD)Expedia
From $678 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 $678 per night (USD)VRBO
From $259 per night (USD)VRBO
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 $259 per night (USD)VRBO
From $321 per night (USD)VRBO
3-bedroom condo in charming Tavernier with AC, WiFi. Relax and unwind
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this charming condo in Tavernier. This delightful property features 3 cozy bedrooms with a mix of a king bed, ...
From $321 per night (USD)VRBO
From $428 per night (USD)VRBO
Ideal Family Haven w/Kitchen, Grill facilities near Breathtaking Ocean access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This listing is for a room within a hotel. ✦ Your room is 1500 sq. ft, equipped with complimentary toiletries, kitchen ...
From $428 per night (USD)VRBO
From $393 per night (USD)VRBO
Perfect Island Getaway! 2 Studio w/Kitchen & Resort amenities - Onsite Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $393 per night (USD)VRBO
From $282 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 $282 per night (USD)Expedia
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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 ...
Click For PricingVRBO
From $559 per night (USD)VRBO
Coconut Hut Oasis - 3 Bedroom Waterfront home with Pool/Spa, Tiki Hut, and Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront Escape with Heated Pool, Dockage & Hot Tub – Bayside Beauty in Islamorada Welcome to your perfect Keys getaw ...
From $559 per night (USD)VRBO
From $876 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 $876 per night (USD)VRBO
From $483 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. ✦ Cl ...
From $483 per night (USD)VRBO
From $727 per night (USD)VRBO
Discover luxury at Stillwater Cove, a stunning 3BR retreat with beautiful pool and dockage.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine w ...
From $727 per night (USD)VRBO
From $556 per night (USD)VRBO
Off The Charts-Waterfront Tiki Bar & Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been ...
From $556 per night (USD)VRBO
From $372 per night (USD)VRBO
NewListing Canal Home Snake Creek with Bay&Ocean Access Tiki&Pool 100ft Dockage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
⭐️5 bedroom 4 bathrooms (One bathroom by pool) ⭐️Canal home in Venetian Shores with access to bay and ocean ⭐️100 foot o ...
From $372 per night (USD)VRBO
From $695 per night (USD)Expedia
Beautiful Pool Home located in Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PROPERTY NAME: Casa Mar 115 Ponce de Leon Blvd, Islamorada, Florida LOCATION: Bayside Canal home located in the popular ...
From $695 per night (USD)Expedia
From $256 per night (USD)VRBO
Paradise in the Heart of Islamorada.Come relax and have the time of your life!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your stunning 2 bed/2 bath “Keys Vibe” condo in the heart of Islamorada—also known worldwide as the Sport‑Fis ...
From $256 per night (USD)VRBO
From $475 per night (USD)VRBO
Relax in this spacious 3BR home in Islamorada with a private pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to 137 Ocean Lane in beautiful Islamorada—your private slice of paradise in the Florida Keys. This charming 3-be ...
From $475 per night (USD)VRBO
From $1139 per night (USD)VRBO
Relax in Sunset Cottage, bayfront 4BR pool home retreat in picturesque Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning, fully renovated retreat checks every box for the perfect Keys escape—sweeping bay views, a private pool a ...
From $1139 per night (USD)VRBO
From $1601 per night (USD)Expedia
Oceanfront Estate - Private Beach, Pool, & Dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Palm Escape – A Private Oceanfront Tropical Estate in the Heart of Islamorada Private Estate - Beach, Pool, & Dock all ...
From $1601 per night (USD)Expedia
From $461 per night (USD)VRBO
Waterfront, Movie Room, HotTub. 1 house, 2 Options
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 11
Discover the beauty of Islamorada & the Florida Keys from this spacious canal-side home! You will slide right into vacat ...
From $461 per night (USD)VRBO
From $178 per night (USD)VRBO
Modern remodeled 2 bedroom Apt - Summer Sea 434
- 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 $178 per night (USD)VRBO
From $741 per night (USD)VRBO
Oceanfront Cottage in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features colorful cottages with premium amenities. Gu ...
From $741 per night (USD)VRBO
From $580 per night (USD)VRBO
Ocean view Studio w/kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $580 per night (USD)VRBO
From $639 per night (USD)VRBO
Oceanfront Studio Queen w/Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $639 per night (USD)VRBO
From $639 per night (USD)VRBO
Ocean Front Studio w/Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $639 per night (USD)VRBO
From $259 per night (USD)VRBO
Welcome to Your Island Escape! Min 28-Day Reservation Required
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine waking up to warm ocean breezes, the gentle sway of palm trees, and the first golden light of the sun rising ove ...
From $259 per night (USD)VRBO
From $1344 per night (USD)VRBO
Two Bedroom Ocean Front Suite w/Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $1344 per night (USD)VRBO
From $746 per night (USD)VRBO
One Bedroom Suite w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $746 per night (USD)VRBO
From $885 per night (USD)VRBO
2 Separate Unites w/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $885 per night (USD)VRBO
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Courtyard View Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
Click For PricingVRBO
From $408 per night (USD)VRBO
2 Queen Beds Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $408 per night (USD)VRBO
From $1106 per night (USD)VRBO
Two Bedrooms Suite w/Ocean View, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $1106 per night (USD)VRBO
From $721 per night (USD)VRBO
2 Suites w/Queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $721 per night (USD)VRBO
Click For PricingVRBO
Courtyard View King Room w/ Balcony, Outdoor Pool & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
Click For PricingVRBO
From $742 per night (USD)VRBO
2 Rooms w/ Balcony, Courtyard View, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $742 per night (USD)VRBO
From $712 per night (USD)VRBO
Turtles Nest Islamorada Getaway 28 day rental
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful home is nestled in the quiet neighborhood of Venetian Shores. It sits right on a deep water canal minutes ...
From $712 per night (USD)VRBO
From $380 per night (USD)VRBO
Charming 3BR canal home in Plantation Key, perfect for family getaways.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away in the sought-after community of Venetian Shores, this 3-bedroom, 2-bath canal-front home is designed for ea ...
From $380 per night (USD)VRBO
From $702 per night (USD)VRBO
Enjoy luxury at Irish Ayes in Islamorada: a spacious 4-bedroom canal home perfect for 8!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Irish Ayes, a stunning 4-bedroom canalfront retreat in the prestigious neighborhood of Venetian Shores, Islam ...
From $702 per night (USD)VRBO
From $312 per night (USD)VRBO
Islamorada Canal front Gem, Newly Renovated 2/2, 26’slip and Quick Bay Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If your trip revolves around time on the water, this is exactly where you want to be. Located on a quiet canal in the he ...
From $312 per night (USD)VRBO
From $1174 per night (USD)VRBO
HeartofMorada: Dock and Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Gated Home | Dock, Heated Pool & 2 Pools | Pet-OK Welcome to HeartofMorada! Step into a private world in Islamorada's m ...
From $1174 per night (USD)VRBO
From $501 per night (USD)Expedia
Islamorada Waterfront Retreat Private Beach, Boat Lift & Canal Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to this fully remodeled waterfront home in Islamorada's exclusive Port Antigua community, set on a wide 130-ft ca ...
From $501 per night (USD)Expedia
From $248 per night (USD)VRBO
Exec Bay Resort-Style 4BR Townhome w/Beach, Marina, Heat/Chill Pool & Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hi! I’m Stephanie, and welcome to our little slice of paradise in Islamorada. My family and I fell in love with Executi ...
From $248 per night (USD)VRBO
From $391 per night (USD)Expedia
3BR oceanfront condo in Islamorada with pool, hot tub, and marina access.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
PROPERTY NAME: Ocean Harbour K4 87851 Old Highway, Islamorada, Florida LOCATION: Ocean Front Condo MINIMUM STAY: 28 Da ...
From $391 per night (USD)Expedia
From $470 per night (USD)VRBO
Waterfront 2BR, 2BA Islamorada retreat with pool, hot tub, and kayaks.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
PROPERTY NAME: The Salty Pelican 163 Paradise Way, Islamorada, FL 33036 LOCATION: Ocean side MINIMUM STAY: 28 Days, A ...
From $470 per night (USD)VRBO
From $358 per night (USD)Expedia
Luxury Waterfront Retreat located in Tavernier, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY NAME: Casa Azalea 263 Azalea Street Tavernier, FL 33070 MM Casa Azalea is a welcoming Tavernier retreat that ...
From $358 per night (USD)Expedia
From $513 per night (USD)VRBO
Beautiful Home in Port Antigua with Dock and Private Beach Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
PROPERTY NAME: Casa Lisbon 125 Lisbon Court, Islamorada, Florida LOCATION: Bayside Canal home located in the popular Is ...
From $513 per night (USD)VRBO
From $1328 per night (USD)Expedia
Islamorada Beach Retreat. Private Beach, Pool, and Boat Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to paradise in this unique Islamorada retreat! Enjoy direct beach access just steps from the front door, while th ...
From $1328 per night (USD)Expedia
From $1269 per night (USD)VRBO
Islamorada Palm Cove - Private Escape, Dock & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Islamorada Palm Cove, a private two-bedroom retreat tucked inside a gated enclave in the heart of Islamorada, ...
From $1269 per night (USD)VRBO
From $412 per night (USD)Expedia
Aqualodge: 2-bedroom house boat with AC in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your Islamorada adventure begins at this 2-bedroom house boat. Step aboard and enjoy a serene escape surrounded by cool ...
From $412 per night (USD)Expedia
From $1240 per night (USD)VRBO
Luxury Bayfront Escape | Pool, Dock, Elevator & Sunset Views
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
It's all about the sunsets...and this stunning bayfront retreat delivers some of the most breathtaking views in the Flor ...
From $1240 per night (USD)VRBO
From $299 per night (USD)Expedia
Bayside - Islamorada Waterfront, 360 Viewing Deck, Htd Swim Spa
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
🏡 Amenities: Canalfront, htd swim spa hot tub, outdoor kitchen, rooftop 360° viewing deck 🌅 Views: Canal, bay, ocean, ...
From $299 per night (USD)Expedia
From $753 per night (USD)VRBO
Coral Key ~ 4 Bed / 3 Bath Canalfront Islamorada Retreat w/ Pool & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Coral Key! Discover a refined yet relaxed waterfront retreat in the heart of Plantation Key at Mile Marker 9 ...
From $753 per night (USD)VRBO
From $237 per night (USD)Expedia
Escape to paradise in beautiful Islamorada, Florida Keys! Newly renovated home.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to paradise in beautiful Islamorada, Florida Keys! Our newly renovated and thoughtfully designed 2-bedroom, 2½-b ...
From $237 per night (USD)Expedia
From $503 per night (USD)VRBO
Casa Paraiso Keys Retreat- Pool, Dock & Family
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to your own Keys hideaway with cozy island‑inspired home, coastal décor and a bright open living/kitchen area tha ...
From $503 per night (USD)VRBO
From $266 per night (USD)Expedia
Coastal 1 Bedroom Unit with 40 foot boat slip
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your home away from home in Tavernier with 1 bedroom, 1 bath. This lovely unit features a cozy queen bed and a comfortab ...
From $266 per night (USD)Expedia
From $147 per night (USD)VRBO
Beautiful 4th floor 1B1b w/open water view #410
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful, clean with a stunning direct open water bay view. Updated kitchen with a new queen size bed and pull-out couc ...
From $147 per night (USD)VRBO
From $322 per night (USD)Expedia
Peaceful Home with Skiff Dockage + Access to Private Bayfront Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
𝗣𝗥𝗢𝗣𝗘𝗥𝗧𝗬 𝗢𝗩𝗘𝗥𝗩𝗜𝗘𝗪 Time Well Wasted is an inviting three-bedroom retreat located in the Port Antigua nei ...
From $322 per night (USD)Expedia
From $620 per night (USD)VRBO
Modern Home with Backyard Oasis — Heated Pool, Putting Green, Bar, Grills, and Dock
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
𝗣𝗥𝗢𝗣𝗘𝗥𝗧𝗬 𝗢𝗩𝗘𝗥𝗩𝗜𝗘𝗪 This beautifully remodeled home in Plantation Key Colony features excellent outdoor l ...
From $620 per night (USD)VRBO
From $627 per night (USD)Expedia
Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
𝗣𝗥𝗢𝗣𝗘𝗥𝗧𝗬 𝗢𝗩𝗘𝗥𝗩𝗜𝗘𝗪 The Garden View Cottage is a charming two-bedroom, one-bath cottage nestled in the ce ...
From $627 per night (USD)Expedia
From $3000 per night (USD)VRBO
Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 22
Welcome to Mermaid's Bay Boutique Estate, an extraordinary bay-front retreat located in the heart of Islamorada. Set beh ...
From $3000 per night (USD)VRBO
From $930 per night (USD)Expedia
Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
𝗣𝗥𝗢𝗣𝗘𝗥𝗧𝗬 𝗢𝗩𝗘𝗥𝗩𝗜𝗘𝗪 The Bay View Cottage is a charming two-bedroom, one-bath cottage tucked beneath the s ...
From $930 per night (USD)Expedia
From $1460 per night (USD)VRBO
Spacious Bayfront Home with Heated Pool, Deep Dockage, Kayaks and More
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
𝗣𝗥𝗢𝗣𝗘𝗥𝗧𝗬 𝗢𝗩𝗘𝗥𝗩𝗜𝗘𝗪 The Dock View House is a spacious four-bedroom, four-and-a-half-bath home located wit ...
From $1460 per night (USD)VRBO
From $458 per night (USD)Expedia
Ocean View : OCEAN VIEW: POOL: ELEVATOR: PET FRIENDLY: GOLF CAR: HOME OFFICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
🌴✨ OCEAN VIEWS • POOL • ELEVATOR • PET FRIENDLY • GOLF CART • BEACH • GYM • HOME OFFICE ✨🌴 FREE CLEANING 🌊 OCEAN VI ...
From $458 per night (USD)Expedia
From $411 per night (USD)VRBO
Waterfront Escape Featuring Private Pool, Hot Tub & 50 ft. Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
🌴 Waterfront Escape in the Heart of Islamorada Your dream Florida Keys getaway awaits—where turquoise waters, tropical ...
From $411 per night (USD)VRBO
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Relaxing waterfront retreat with boat dock & amazing ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we c ...
Click For PricingExpedia
From $233 per night (USD)VRBO
Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
✨ Tollgate Tides blends comfort and adventure in one perfect waterfront escape. Whether you're here for fishing, snorkel ...
From $233 per night (USD)VRBO
From $244 per night (USD)Expedia
Canalfront, Dog-Friendly Home with High-Speed WiFi, Private Boat Ramp, and Kayak
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Book this newly renovated home that sits on a major canal, where guests can tie off a boat, in the Indian Waterways neig ...
From $244 per night (USD)Expedia
From $133 per night (USD)VRBO
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Whether you spend your Florida vacation splashing in the cool surf or unwinding with friends on your private patio, you' ...
From $133 per night (USD)VRBO
From $538 per night (USD)Expedia
Beautiful house in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Discover the beauty of Islamorada from this 4-bedroom house. Inside, guests find a wonderful mix of sleeping options, in ...
From $538 per night (USD)Expedia
From $783 per night (USD)VRBO
Bayfront Serenity. 4 En-Suite Bedrooms. 1/2 bath. Elevator. Pool. Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Serenity | Seasonal Waterfront Retreat | 4 En-Suite Bedrooms | Pool, Dock & Sunsets | Elevator. Tesla Charger. ...
From $783 per night (USD)VRBO
From $332 per night (USD)Expedia
Surf Shack - Downtown Islamorada 2 Bedroom Beach Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Surf Shack, your laid-back beach bungalow escape in the heart of Islamorada. Tucked along a quiet street in d ...
From $332 per night (USD)Expedia
From $257 per night (USD)VRBO
Turtle House Islamorada - 3 Bed/3 Bath Pool Home, Private Beach, Best Location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Located in the heart of Islamorada, our home sits on a private road with beach access. Enjoy 3 bedrooms with en-suite ba ...
From $257 per night (USD)VRBO
From $1412 per night (USD)VRBO
One Ten Palms ~ Charming Islamorada Beachfront Home with Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to One Ten Palms! Escape to paradise at this private oceanfront estate in Islamorada, where the laid-back spir ...
From $1412 per night (USD)VRBO
From $2163 per night (USD)VRBO
Private Beachfront Estate with Resort-Style Pool & Pier
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to a private beachfront estate in on the Atlantic ocean in Islamorada where refined comfort meets the ease of a ...
From $2163 per night (USD)VRBO
From $273 per night (USD)VRBO
Tackle Shop Suite in lovely Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to this charming hotel in Islamorada. This fantastic property boasts one bathroom with refreshing showers, perfe ...
From $273 per night (USD)VRBO
From $1116 per night (USD)VRBO
Islander Resort Stay | 7 mi to San Pedro Pk | Dive & Explore Waters
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along the scenic Overseas Highway in Islamorada, this resort offers a tranquil oceanfront retreat with direct beach ...
From $1116 per night (USD)VRBO
From $1159 per night (USD)VRBO
Sunset Stay | 3 mi to Diving Museum | Explore Marine Life
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Set along the scenic Overseas Highway in Islamorada, this resort offers direct access to beautiful ocean views and water ...
From $1159 per night (USD)VRBO
From $942 per night (USD)VRBO
Ocean Escape | 2 mi to Founders Pk | Bike Coastal Paths
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on the scenic Overseas Highway in Islamorada, this resort offers easy access to the area's beautiful beaches and ...
From $942 per night (USD)VRBO
From $1414 per night (USD)VRBO
Seaview Kitchen Pool Gym | 4 mi to Theater Sea | Swim with Dolphins
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Situated on the scenic Overseas Highway in Islamorada, this resort offers direct access to beautiful ocean views and wat ...
From $1414 per night (USD)VRBO
From $1456 per night (USD)VRBO
Reef w/ Pool+Gym Access | 7 mi to San Pedro Pk | Scuba & Snorkel Trips
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Situated on the scenic Overseas Highway in Islamorada, this resort offers easy access to local beaches and water activit ...
From $1456 per night (USD)VRBO
From $432 per night (USD)VRBO
Ocean Escape | 2 mi to Founders Pk | Bike Coastal Paths
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers direct access to beautiful beaches and ...
From $432 per night (USD)VRBO
From $522 per night (USD)VRBO
Sunset Stay| 3 mi to Diving Museum | Explore Marine Life
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to local fishing spots and ...
From $522 per night (USD)VRBO
From $864 per night (USD)VRBO
Islander Resort | 2 Units | 6 mi to Robbies | Fishing & Boat Trips
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on the scenic Overseas Highway in Islamorada, this oceanside resort offers easy access to local beaches and wate ...
From $864 per night (USD)VRBO