Find short term rentals in Islamorada, FL at the best prices

971 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Islamorada, FL short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Islamorada, FL

Best family friendly Islamorada, FL Short term rentals

Among the 971 accommodations in Islamorada, FL, here are the 4 best family friendly rentals

Charming Cabana-condo In Picturesque Tavernier - Islamorada, FL
10 64 reviews
Islamorada, FL
20/06 – 27/06
$574/nighttotal: $4018 (7 )

Charming Cabana-condo In Picturesque Tavernier

2 6
apartment , Tavernier
This two-bedroom apartment is located in Tavernier, Florida, within a 2.4 kilometre walk of Baker's Cay Resort Beach and Harry Harris Park, making it ideal for exploring the area's natural beauty. The property has received excellent user ratings and is perfect for families or groups of friends.
The 85 square metre apartment can comfortably accommodate up to six guests and boasts a fully equipped kitchen, air conditioning, and a private garden. Guests can enjoy the on-site swimming pool, Jacuzzi, and tennis court, as well as the nearby beach and other attractions.
Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-friendly - Islamorada, FL
10 7 reviews
Islamorada, FL
08/09 – 06/10
$526/nighttotal: $14728 (28 )

Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-friendly

3 4
apartment , Islamorada, Village of Islands
This Islamorada oceanfront apartment, situated in a gated community near the History of Diving Museum and Keys History & Discovery Centre, offers privacy and easy access to local breweries and water sports.
The 156 square metre (1679 square foot) property boasts three bedrooms sleeping seven, three bathrooms, a terrace, swimming pool, garden, parking, and features including a fully equipped kitchen, WiFi, and a washing machine.
Chateau On The Ocean - The Southernmost Shangrila - Islamorada, FL
Islamorada, FL
19/07 – 26/07
$20922/nighttotal: $146454 (7 )

Chateau On The Ocean - The Southernmost Shangrila

1 9
apartment , Islamorada, Village of Islands
This oceanfront estate in Islamorada, Village of Islands, offers direct Atlantic frontage with 120 metres of private beach and a 100-metre private deep-water dock, located approximately 145 kilometres from Miami.
This luxury villa accommodates up to 14 guests with 11 bathrooms, featuring a resort-style mosaic pool, a 288 square metre Baccarat-inspired ballroom, a 3,000+ square metre Skyline Terrace with 360° ocean views, and a fitness centre.
Brand New Home-  Islamorada On Ocean With Views - Islamorada, FL
10 1 review
Islamorada, FL
24/12 – 02/01
$1803/nighttotal: $16227 (9 )

Brand New Home- Islamorada On Ocean With Views

1 2
apartment , Islamorada, Village of Islands
This three-bedroom, two-bathroom oceanfront property in Islamorada, Village of Islands, boasts direct beach access and is situated near a boat marina.
Offering panoramic ocean views, a private pool with a waterfall and poolside bar, a gourmet kitchen with a large island, elevator access, and sleeps up to 15 guests, this brand-new luxury apartment provides unparalleled amenities.

Best Islamorada, FL lodging with a balcony

Two Spectacular Ocean Views From The Living Room And Master Bedroom Of The Condo - Islamorada, FL
9.6 224 reviews
Islamorada, FL
18/07 – 22/07
$502/nighttotal: $2008 (4 )

Two Spectacular Ocean Views From The Living Room And Master Bedroom Of The Condo

3 4
apartment , Tavernier
This Tavernier apartment is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches and natural attractions of the Florida Keys. It has been rated excellent by previous guests.
The apartment has two bedrooms and can comfortably accommodate six guests. It comes with a fully equipped kitchen, a balcony, a swimming pool, a jacuzzi, a sauna, a spa, and parking, providing plenty of space and amenities for a relaxing and enjoyable stay.
Ocean View Corner Penthouse Ocean Pointe 5416 - Islamorada, FL
9.9 186 reviews
Islamorada, FL
09/07 – 12/07
$714/nighttotal: $2142 (3 )

Ocean View Corner Penthouse Ocean Pointe 5416

2 5
apartment , Tavernier
This penthouse apartment is located in Ocean Pointe Suites, midway between Key Largo and Islamorada in the Florida Keys, offering easy access to both locations, approximately 80km from each. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The two-bedroom, two-bathroom apartment can comfortably accommodate up to six guests. Amenities include a private beach, pier, marina, swimming pool, jacuzzi, tennis and pickleball courts, and a basketball hoop. Guests can also enjoy direct ocean views from the balcony and living area, and access to a range of water activities such as fishing, diving, snorkeling, paddleboarding, and kayaking.
Breathtaking Ocean Views! Owners Who Care. Sangria Sunrise! 10% Off Charters! - Islamorada, FL
9.9 189 reviews
Islamorada, FL
18/07 – 22/07
$598/nighttotal: $2392 (4 )

Breathtaking Ocean Views! Owners Who Care. Sangria Sunrise! 10% Off Charters!

1 4
apartment , Tavernier
This Tavernier apartment is directly on the beach, just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. The property has received excellent ratings for location, cleanliness, and overall experience.
The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square metres, suitable for up to four guests. Amenities include a fully equipped kitchen, a swimming pool, a jacuzzi, a terrace, a garden, and parking.
Condo ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
Islamorada, FL
08/09 – 06/10
$305/nighttotal: $8540 (28 )

Condo ∙ 2 Bedrooms ∙ 4 Guests

2 4
apartment , Islamorada, Village of Islands
Beacon Reef #503, a two-bedroom condo in Islamorada, Village of Islands, is situated at mile marker 83.2, offering easy access to local restaurants and fishing/diving opportunities.
This fifth-floor apartment boasts ocean views, sleeps four guests, includes a king-size bed, two full-size beds, two bathrooms, a private balcony, and access to a swimming pool, hot tub, fitness centre, and other Beacon Reef amenities.

Frequently Asked Questions about short term rentals in Islamorada, FL

Destinations nearby

Best Islamorada, FL lodging with a kitchen

Bay Harbour Islamorada Oceanfront Views 3/2.5 Updated Condo Dock - Islamorada, FL
10 21 reviews
Islamorada, FL
24/12 – 02/01
$1328/nighttotal: $11952 (9 )

Bay Harbour Islamorada Oceanfront Views 3/2.5 Updated Condo Dock

3 2
apartment , Islamorada, Village of Islands
This waterside condominium is located in the gated Bay Harbour community at mile marker 77.5 bayside in Matecumbe, Islamorada, within 1.6 kilometres of Anne's Beach and the San Pedro Underwater Archaeological Preserve State Park.
This three-bedroom holiday flat, accommodating up to six guests, offers a private screened terrace with ocean views, a gourmet kitchen, a private 9.45-metre protected dock with a boat lift, and on-site access to a swimming pool and spa.
Marina To Ocean View Key Largo Ocean Pointe 5308 - Islamorada, FL
9.4 70 reviews
Islamorada, FL
09/10 – 12/10
$431/nighttotal: $1293 (3 )

Marina To Ocean View Key Largo Ocean Pointe 5308

2 2
apartment , Tavernier
This Tavernier waterfront apartment, situated 1.1 kilometres from Harry Harris Park and within 4.8 kilometres of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views.
The 84 square metre property features three bedrooms, two bathrooms, a sofa bed for a total guest capacity of four, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and parking.
Unbeatable Views From Lux Oceanfront Suite - Islamorada, FL
9.8 53 reviews
Islamorada, FL
24/07 – 26/07
$679/nighttotal: $1358 (2 )

Unbeatable Views From Lux Oceanfront Suite

2 2
apartment , Tavernier
This Tavernier waterfront apartment, a short walk (under 2.4km) from Baker's Cay Resort Beach and Harry Harris Park, and within 5km of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views.
The 85 square metre property features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, swimming pool, jacuzzi, tennis court, and free Wi-Fi.
Keys Deal W/cafe & Pool Bar! Up To 20% Off Oceanfront 2/2 With Private Beach - Islamorada, FL
9.7 287 reviews
Islamorada, FL
23/07 – 26/07
$573/nighttotal: $1719 (3 )

Keys Deal W/cafe & Pool Bar! Up To 20% Off Oceanfront 2/2 With Private Beach

2 2
apartment , Tavernier
This Tavernier apartment is conveniently located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property has received excellent ratings for user experience, location, and cleanliness.
The two-bedroom apartment spans 79 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.

Best Islamorada, FL lodging with laundry available

Key Largo 2br Condo - Ocean View, Pool, And Beach - Islamorada, FL
Islamorada, FL
03/07 – 05/07
$799/nighttotal: $1598 (2 )

Key Largo 2br Condo - Ocean View, Pool, And Beach

2 5
apartment , Tavernier
This Tavernier oceanfront apartment, near Key Largo and Islamorada, offers direct beach access and proximity to John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre.
The 79-square-metre (850-square-foot) property features two bedrooms, two bathrooms, sleeps six, and includes a kitchen with fridge, microwave, and dishwasher, plus a swimming pool and parking; on-site resort amenities such as a junior Olympic-sized swimming pool and tennis courts are also available.
Luxurious Suite+open Ocean Views+pool & Cabana Bar - Islamorada, FL
9.8 241 reviews
Islamorada, FL
24/07 – 26/07
$778/nighttotal: $1556 (2 )

Luxurious Suite+open Ocean Views+pool & Cabana Bar

2 2
apartment , Tavernier
This waterfront apartment is located in Tavernier, just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and relaxing atmosphere. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is spacious, covering 85 square metres and comfortably accommodating up to six guests. It features a fully equipped kitchen, a washing machine, a balcony, a Smart TV, and access to a swimming pool, spa, tennis court, and barbecue grills, ensuring a comfortable and enjoyable stay.
Ocean Front Townhouse With Breathtaking Views! - Islamorada, FL
10 1 review
Islamorada, FL
30/07 – 06/08
$536/nighttotal: $3752 (7 )

Ocean Front Townhouse With Breathtaking Views!

1 2
apartment , Islamorada, Village of Islands
This oceanfront townhouse in Islamorada, Village of Islands, boasts direct beach access and is conveniently located near local restaurants and water activities, though precise distances aren't specified.
Sleeping seven comfortably, this two-bedroom, one-bathroom property features a king-size bed, daybed, and pull-out sofa, a fully equipped kitchen, and access to a gated community with a heated pool and fishing pier; towels and linens are provided.
Bungalow #5 - 2 Bed/1 Bath & Pool In Islamorada - Islamorada, FL
9.6 20 reviews
Islamorada, FL
09/08 – 14/08
$576/nighttotal: $2880 (5 )

Bungalow #5 - 2 Bed/1 Bath & Pool In Islamorada

2 2
apartment , Islamorada, Village of Islands
This charming bungalow is situated in the Matecumbe neighbourhood of Islamorada, within easy reach of Bud n' Mary's Dive Center and Florida Keys Brewing Co., offering a peaceful retreat in a vibrant area. It has consistently received excellent user ratings, making it a popular choice for travellers.
The bungalow features two bedrooms and one bathroom, providing comfortable accommodation for a small family or group of friends. Guests can enjoy a private backyard, a community heated pool, and the convenience of air conditioning, internet access, and pet-friendly policies.
©2026 cozycozy.com