
Holiday rentals with a pool in Islamorada
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Top-rated rentals with a pool in Islamorada
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Sugar Cane - Florida Keys tropical retreat
We have just completely renovated this condo at Ocean Pointe Resort and it's Insta-worthy. Every detail has been designed and considered. Sugar Cane is conveniently located near the best of the Florida Keys - close to Islamorada and Key Largo. The property boasts a large outdoor pool with a pool bar, hot tub, oceanfront beach and boardwalk, boat ramp, marina, tennis courts and children's play area. We manage Sugar Cane ourselves and live nearby so we have local knowledge and are very responsive

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Toes in the Sand - 2 Bedroom Condo Sleeps 4
2-bedrooms, 2 full baths located on the 4th floor with ocean views. This condo has a beach, viewing pier, rentable boat slips, & boat trailer storage, café and a very large heated pool with a bar and gated entry with 24 hour security! Perfectly located between Key Largo and Islamorada, close to Pennekamp State Park, Harry Harris State Park, popular restaurants on the water, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

Ocean Pointe 2309 with Ocean Views
Come and enjoy all the activities the Florida Keys has to offer from this new inviting oceanfront condo. Your vacation begins the moment you drive into our 60 acre Ocean Pointe property. The Jr. Olympic sized heated pool is surrounded by beautiful landscaping, a hot tub, & the Mermaid bar. Other amenities include: a sandy beach, a Marina for boats up to 28ft, a ramp, tennis courts, pickle ball court, children's swings, charcoal grills, picnic tables, pier, cafe bar & lounging areas.

Blue Haven Key Largo | Ocean Pointe 1315
Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

Ocean Views at Ocean Pointe
Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated & is beautifully designed with comfortable, beach chic decor. It offers an abundance of natural light surrounded by windows overlooking lush landscaping and the Atlantic Ocean. Ocean Pointe Suites offers a private sandy beach, a junior Olympic sized pool, a 14-person spa, a boardwalk, a pickleball court, deep-water marina, gazebo, 2 tennis courts & more!

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Exquisite Oceanfront Paradise - Key Colony Beach
Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.
Popular amenities for Islamorada rentals with a pool
House rentals with a pool

Cancellation Deal: March 21 thru March 28

Blue House Marine in Key Largo

Florida Keys Cottage with Pool - Hawks Cay Resort

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

The Paradise 2

Waterfront Home 37.5-ft dock, Cabana Club Included

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Escape to the Seaside!
Apartment rentals with a pool

Deluxe Oceanfront 1/1 sleeps 4. Cafe & Pool Bar.

Reel Large END Unit in Ocean Point Suites

Your Happy Place - Oceanfront

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Condo in Tavernier

Island Getaway at Ocean Point

Tequila Sunrise

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Other holiday rentals with a pool

Islamorada house with best location. Lic # 24-0055

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Knight's Key Suites Deluxe Double Room w/ Kitchen

Oceanfront 3‑Stories of Bliss • Dockage & Gameroom

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Bayview Beautiful townhouse in Islamorada, FL KEYS

Bohemian Beach Bungalow
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £276 | £323 | £335 | £276 | £374 | £269 | £315 | £274 | £271 | £228 | £245 | £282 |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about holiday rentals with a pool in Islamorada

Total holiday rentals
Explore 620 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at £52 per night before taxes and fees

Verified guest reviews
Over 4,040 verified reviews to help you choose

Family-friendly holiday rentals
420 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 320 rentals that welcome pets

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wifi availability
620 of Islamorada holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islamorada rentals

4.7 Average rating
Islamorada stays receive an average rating of 4.7 out of 5 from guests
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Calusa Campground
- Biscayne National Park
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- History Of Diving Museum
- Everglades Alligator Farm
- Conch Key
- Monkey Jungle
- Long Beach
- Theater of the Sea
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Key Largo Kampground And Marina
- Homestead-Miami Speedway
- Sunset Park
- Curry Hammock State Park
- Dolphin Research Center




