Best apartment offers in Big Pine Key, FL

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Big Pine Key, FL apartments
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319 Best apartments in Big Pine Key, FL

Search Apartments by the Shore Big Pine Key, FL

Enjoy the regional coastline from comfortable shoreside holiday apartments located a short drive from beaches in Big Pine Key, FL.

Charming 2-bedroom House With Wifi, Ac In Lovely Cudjoe Key - Big Pine Key, FL
9.8 6 reviews

Charming 2-bedroom House With Wifi, Ac In Lovely Cudjoe Key

apartment, Cudjoe Key
This two-bedroom, two-bathroom holiday home is situated in Summerland Key, near Cudjoe Key, offering easy access to Bahia Honda State Park and other Florida Keys attractions.
The property sleeps four in two double bedrooms, includes air conditioning, Wi-Fi, a washing machine, and a $130 amenity fee payable on arrival; note that distances to local beaches and attractions are not specified.

Our Favourite Family-Friendly Holiday Apartments in Big Pine Key, FL

Family holidays in Big Pine Key, FL work best when your apartment features plenty of room and easy access to lifeguarded beaches.

Beautiful Family-friendly, Dock, Marina, Heated Pool, Near Key West, Mm21.5 - Big Pine Key, FL
10 243 reviews

Beautiful Family-friendly, Dock, Marina, Heated Pool, Near Key West, Mm21.5

apartment, Cudjoe Key
This waterfront house is located in Summerland Key, just under 5 kilometres from Upper Sugarloaf Key and Upper Sugarloaf Sound.
The 111 square metre property offers two bedrooms, three bathrooms, and a comfortable living space for up to six guests, complete with a fully equipped kitchen, air conditioning, a private pool and a terrace.
Oceanside Home, Dock,kayaks,bikes,pool,fishing,107 - Big Pine Key, FL
9.8 197 reviews

Oceanside Home, Dock,kayaks,bikes,pool,fishing,107

apartment, Cudjoe Key
This waterfront property is located on Cudjoe Key, just two miles from Upper Sugarloaf Key and Upper Sugarloaf Sound, offering stunning views and easy access to the surrounding area's natural beauty. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The two-bedroom, three-bathroom house spans 111 square metres and comfortably accommodates up to six guests. This family-friendly property offers a range of amenities for a relaxing and enjoyable stay, including a private swimming pool, a fitness centre, a garden, a terrace, and a fully equipped kitchen.
Oceanfront 2br Retreat - 35' Dock, Sunrise Views, Boater's Paradise - Big Pine Key, FL
9.6 53 reviews

Oceanfront 2br Retreat - 35' Dock, Sunrise Views, Boater's Paradise

apartment, Cudjoe Key
Coconut Telegraph #221 is a two-bedroom flat located in the private, gated Venture Out community on Cudjoe Key, offering direct oceanfront access and a 35-foot dock, situated a 10-minute drive from local restaurants and 32 kilometres from Key West. This 80-square-metre holiday let accommodates four guests and boasts amenities including a swimming pool, jacuzzi, spa, tennis court, and a full kitchen, with easy access to Looe Key for snorkelling and diving, and proximity to both Atlantic and Gulf fishing spots.
3 Night Minimum! Spectacular Ocean Views! - Big Pine Key, FL
8.6 29 reviews

3 Night Minimum! Spectacular Ocean Views!

apartment, Cudjoe Key
This two-bedroom property is located in Summerland Key, just 6 kilometres from Upper Sugarloaf Key and Florida Keys Beaches, offering a peaceful escape from the hustle and bustle. It has received very good user ratings.
The house is suitable for families or groups of up to six people and features a fully equipped kitchen, a terrace, a garden, a swimming pool, and a tennis court. Guests can enjoy the peace and quiet of the surrounding area, or take advantage of the many activities and attractions that Cudjoe Key has to offer.

Frequently asked questions about apartment rentals in Big Pine Key, FL

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Find the Best Pet-Friendly Holiday Apartments in Big Pine Key, FL

Explore the coast from a dog-friendly holiday apartment in Big Pine Key, FL, tailored for owners and their dogs.

Private Secluded Ocean View & Pool Near Key West - Big Pine Key, FL
8.0 112 reviews

Private Secluded Ocean View & Pool Near Key West

apartment, Cudjoe Key
This eco-friendly holiday home is located in Summerland Key, just 15 minutes' drive from Key West Golf Club, the beach, restaurants, and shops. The property is rated very good by previous guests and offers a tranquil tropical setting.
This four-bedroom, two-bathroom house provides 297 square metres of space and sleeps up to 10 guests. Amenities include a swimming pool, Jacuzzi, terrace, garden, spa, parking, and a kitchen equipped with a fridge, microwave oven, and dishwasher.
Ocean Front Paradise/290 Ft Private Dock/awesome Views - Big Pine Key, FL
9.0 213 reviews

Ocean Front Paradise/290 Ft Private Dock/awesome Views

apartment, Big Pine Key
This apartment is situated on Big Pine Key, just 3km from Winn Dixie grocery store and a short drive from the Key Deer National Wildlife Refuge and Bahia Honda State Park. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The apartment has two separate units, accommodating up to 8 guests. It boasts a private dock with mooring, a fish cleaning station, and a picnic island, perfect for enjoying the area's fishing and diving opportunities.
Reel Island Retreat #273 At Venture Out In The Florida Keys - Big Pine Key, FL
8.6 9 reviews

Reel Island Retreat #273 At Venture Out In The Florida Keys

apartment, Cudjoe Key
This Cudjoe Key waterfront holiday home, situated in the Venture Out community of Summerland Key, is a 20-minute drive from Key West.
The 76-square-metre (820 sq ft) property boasts three bedrooms, two bathrooms, sleeps six, and includes a private dock, Tiki bar, swimming pool, Jacuzzi, tennis court, and is close to restaurants such as the Square Grouper and Morning Joint.
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-friendly - Big Pine Key, FL
10 9 reviews

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-friendly

apartment, Cudjoe Key
This oceanfront apartment, situated within the Venture Out community on Cudjoe Key, offers direct access to a 35-foot seawall, perfect for docking boats up to 10 metres, and is a short drive from Key West and local restaurants such as the Square Grouper.
The 80-square-metre property boasts two bedrooms (king and twin beds convertible to a king), two bathrooms, a queen-size sofa bed, a fully equipped kitchen with stainless steel appliances, and access to Venture Out's amenities including a heated pool, jacuzzi, and tennis courts; accommodating up to six guests.

Explore Holiday Apartments with a Pool in Big Pine Key, FL

Dip in whenever you like, as every holiday apartment near the water in Big Pine Key, FL comes with a swimming pool on-site.

Sailfish Haven #390 - Ocean Views, 35' Seawall - Big Pine Key, FL
9.0 8 reviews

Sailfish Haven #390 - Ocean Views, 35' Seawall

apartment, Cudjoe Key
This Cudjoe Key waterfront apartment, situated within the Venture Out community, offers direct access to the ocean and is a 32km drive from Key West.
The 77 square metre property sleeps six, boasting three bedrooms, two bathrooms, a fully equipped kitchen including a slow cooker and wine chiller, plus access to two kayaks, two bicycles, and Venture Out's communal pool, Jacuzzi and tennis courts.
Lower Keys Paradise - Big Pine Key, FL
9.8 38 reviews

Lower Keys Paradise

apartment, Cudjoe Key
This Cudjoe Key property is located just a 6 kilometre drive from Upper Sugarloaf Key and Florida Keys Beaches, offering easy access to the area's natural beauty. It has received excellent user reviews, suggesting a comfortable and enjoyable stay.
The two-bedroom house covers 84 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, air conditioning, a private pool and jacuzzi, plus a terrace and garden, making it ideal for a relaxing and enjoyable holiday.
Frigate's Nest Extraordinary 8bed/8bath Nightly Rental With Dockage & Private Pool - Big Pine Key, FL
8.8 6 reviews

Frigate's Nest Extraordinary 8bed/8bath Nightly Rental With Dockage & Private Pool

apartment, Big Pine Key
This waterfront residence is located in Little Torch Key, approximately 4.8 kilometres from Looe Key Reef and a short drive from the lower Florida Keys' islands.
This exclusive eight-bedroom, eight-bathroom holiday home accommodates sixteen guests and features a private pool, dockage for boats up to 10.6 metres, and kayaks, offering direct open water views.
Treasure Isle At Parks End - Venture Out 062 - Big Pine Key, FL
8.8 5 reviews

Treasure Isle At Parks End - Venture Out 062

apartment, Cudjoe Key
This Cudjoe Key seaside property is a 3-bedroom house, situated within a 2.4 km radius of Florida Keys Beaches and a 15-minute walk from Venture Out Keys, Venture Key, and Out Key.
The 70 square metre dwelling boasts a private balcony, swimming pool, jacuzzi, and fully equipped kitchen, sleeping up to four guests and offering free Wi-Fi in communal areas.

Best Big Pine Key, FL holiday apartments with air conditioning

1 Bedroom Cabin Half/duplex Unit A Up On Stilts - Big Pine Key, FL
8.8 108 reviews

1 Bedroom Cabin Half/duplex Unit A Up On Stilts

apartment, Big Pine Key
Barnacle Resort House - Big Pine Key, FL
8.2 10 reviews

Barnacle Resort House

apartment, Big Pine Key
Enjoy Caribbean Weather In The Usa. Openings August 2026 Forward! - Big Pine Key, FL
9.4 143 reviews

Enjoy Caribbean Weather In The Usa. Openings August 2026 Forward!

apartment, Cudjoe Key
Mahi House #440 Waterfront Retreat With Dock, Pool & Optional Golf Cart - Big Pine Key, FL
9.4 6 reviews

Mahi House #440 Waterfront Retreat With Dock, Pool & Optional Golf Cart

apartment, Cudjoe Key

Best 5-Star Holiday Apartments in Big Pine Key, FL

A carefully selected luxury holiday apartment in Big Pine Key, FL elevates your stay with premium interiors and a location worth the journey.

Relax By Florida Keys Beaches, Just A 7-min Drive Away - Big Pine Key, FL
9.6 214 reviews

Relax By Florida Keys Beaches, Just A 7-min Drive Away

apartment, Cudjoe Key

Top-Rated Holiday Apartments with Parking in Big Pine Key, FL

Parking is sorted from the start, as these holiday apartments near the water in Big Pine Key, FL include free on-site spaces for your stay.

Tropical Island Paradise W / Open Water Views! - Big Pine Key, FL
9.6 110 reviews

Tropical Island Paradise W / Open Water Views!

apartment, Cudjoe Key
Anchor House - Big Pine Key, FL
9.9 139 reviews

Anchor House

apartment, Big Pine Key
Bimini Breeze - Vo 313 - Big Pine Key, FL
9.4 3 reviews

Bimini Breeze - Vo 313

apartment, Cudjoe Key
Your Perfect Florida Keys Escape - Big Pine Key, FL
No reviews

Your Perfect Florida Keys Escape

apartment, Big Pine Key

Browse Holiday Apartments with a Hot Tub in Big Pine Key, FL

An apartment with a hot tub near the water in Big Pine Key, FL is perfectly suited for a private, relaxing soak after a day by the sea.

Waterfront Getaway With 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors - Big Pine Key, FL
8.0 1 review

Waterfront Getaway With 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

apartment, Cudjoe Key
Blue Lobster Lodge #543 Open Coastal Retreat With Pool Near Key West - Big Pine Key, FL
8.8 11 reviews

Blue Lobster Lodge #543 Open Coastal Retreat With Pool Near Key West

apartment, Cudjoe Key
Seascape Vacation!!! - Big Pine Key, FL
8.2 71 reviews

Seascape Vacation!!!

apartment, Cudjoe Key
Updated 2br/2ba Venture Out Home W/ Pool Access, Pet Friendly, Near Key West - Big Pine Key, FL
8.0 3 reviews

Updated 2br/2ba Venture Out Home W/ Pool Access, Pet Friendly, Near Key West

apartment, Cudjoe Key

Choose the Right Holiday Apartments with a Balcony in Big Pine Key, FL

Having views of the water and coastal scenery from your own private balcony is a detail that elevates any stay in Big Pine Key, FL.

Sirena Key Cottage In Venture Out - Big Pine Key, FL
8.0 18 reviews

Sirena Key Cottage In Venture Out

apartment, Cudjoe Key
Ocean View High-rise In Venture Out | Pool, Boat Ramp & Close To Key West - Big Pine Key, FL
10 2 reviews

Ocean View High-rise In Venture Out | Pool, Boat Ramp & Close To Key West

apartment, Cudjoe Key
Oceanside Paradise  Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle Ball - Big Pine Key, FL
9.8 258 reviews

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle Ball

apartment, Cudjoe Key
Waterfront 2br/2ba | 35' Seawall For 32' Boat | Beautiful Sunrises On Cudjoe Key - Big Pine Key, FL
10 4 reviews

Waterfront 2br/2ba | 35' Seawall For 32' Boat | Beautiful Sunrises On Cudjoe Key

apartment, Cudjoe Key
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