Holiday Rentals in Cudjoe Key, FL

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Cudjoe Key, FL holiday rentals
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438 Holiday rentals and Airbnb in Cudjoe Key, FL

Best family friendly Cudjoe Key, FL holiday rentals

Among the 438 accommodations in Cudjoe Key, FL, here are the 4 best family friendly rentals

Reel Island Retreat #273 At Venture Out In The Florida Keys - Cudjoe Key, FL
8.6 9 reviews
Cudjoe Key, FL
29/08 – 03/09
289 €/nighttotal: 1445 € (5 )

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

2 4
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.
Pelican's Roost, Waterfront Comfort At Venture Out - Cudjoe Key, FL
8.9 23 reviews
Cudjoe Key, FL
29/08 – 03/09
311 €/nighttotal: 1555 € (5 )

Pelican's Roost, Waterfront Comfort At Venture Out

2 4
house , Cudjoe Key
This beachfront property is situated on Cudjoe Key, a mere 37 kilometres from both the Ernest Hemingway Home and Museum and Duval Street in Key West.
The two-bedroom house, spanning 80 square metres, offers a private pool, hot tub, tennis court and a fully equipped kitchen, accommodating up to nine guests.
Open Water View From Porch , Golf Cart, Dock, Bikes, Kayaks, Trailer Parking - Cudjoe Key, FL
9.8 138 reviews
Cudjoe Key, FL
29/08 – 03/09
442 €/nighttotal: 2210 € (5 )

Open Water View From Porch , Golf Cart, Dock, Bikes, Kayaks, Trailer Parking

2 4
apartment , Cudjoe Key
This waterfront holiday home is located on Cudjoe Key, just 6 kilometres from Upper Sugarloaf Key and Florida Keys Beaches, providing easy access to the area's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The 81 square metre property offers two bedrooms and can accommodate up to four guests. It boasts a range of amenities, including a swimming pool, jacuzzi, spa, tennis court, and a barbecue grill, making it perfect for relaxation and entertainment.
Key Lime Hideaway - Oceanfront Gated Community, Amenities, 3br Stilted Retreat - Cudjoe Key, FL
Cudjoe Key, FL
29/08 – 03/09
357 €/nighttotal: 1785 € (5 )

Key Lime Hideaway - Oceanfront Gated Community, Amenities, 3br Stilted Retreat

3 4
apartment , Cudjoe Key
This three-bedroom, two-bathroom holiday home is located in the Venture Out gated community on Cudjoe Key, a short drive from Key West and other Florida Keys attractions.
The 78-square-metre property boasts a fully equipped kitchen, private patio, access to a community pool, Jacuzzi, tennis courts, and marina store, comfortably sleeping six guests and offering ocean views from both porches.

Best Cudjoe Key, FL holiday rentals with a pool

Among the 438 accommodations in Cudjoe Key, FL, here are the 4 best rentals with a pool

2bd/1ba Waterfront Retreat W/35’ Dock - Cudjoe Key, FL
9.6 28 reviews
Cudjoe Key, FL
29/08 – 03/09
214 €/nighttotal: 1070 € (5 )

2bd/1ba Waterfront Retreat W/35’ Dock

1 4
apartment , Cudjoe Key
This Cudjoe Key waterfront holiday home is situated within the Venture Out community, offering easy access to restaurants such as the Square Grouper and the Niles Road Nature Trail.
Sleeping up to five guests, this two-bedroom, one-bathroom property boasts a private pool and jacuzzi, direct ocean access, and is close to Murray's Market for grocery shopping.
Bimini Breeze - Vo 313 - Cudjoe Key, FL
9.4 3 reviews
Cudjoe Key, FL
25/07 – 01/08
448 €/nighttotal: 3136 € (7 )

Bimini Breeze - Vo 313

2 5
apartment , Cudjoe Key
This Cudjoe Key seaside property is situated within 14.5 kilometres of Upper Sugarloaf Key, Florida Keys Beaches, Lower Sugarloaf Sound, the Big Pine Key Flea Market, and the National Key Deer Refuge Visitor Centre.
This three-bedroom, one-bathroom house offers 70 square metres of space, sleeping up to six guests and boasting a swimming pool, jacuzzi, terrace, garden, parking, and free Wi-Fi; barbecue facilities are also available for al fresco dining.
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key - Cudjoe Key, FL
9.8 21 reviews
Cudjoe Key, FL
04/08 – 07/08
303 €/nighttotal: 909 € (3 )

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2 2
apartment , Cudjoe Key
This Cudjoe Key holiday home is located in the Venture Out gated community, offering easy access to the ocean and local amenities.
The two-bedroom, one-bathroom dwelling sleeps six guests and boasts a fully equipped kitchen, private garden, swimming pool, jacuzzi, and access to community tennis and bocce courts; bikes and a tricycle are also provided.
232 M² House ∙ 5 Bedrooms ∙ 10 Guests - Cudjoe Key, FL
10 2 reviews
Cudjoe Key, FL
19/09 – 26/09
739 €/nighttotal: 5173 € (7 )

232 M² House ∙ 5 Bedrooms ∙ 10 Guests

5 8
house , Cudjoe Key
This five-bedroom, three-bathroom detached residence, offering accommodation for ten guests, is situated within a secluded, gated 8-hectare estate in the Florida Keys wildlife preserve, just 24 kilometres from Key West's shops and nightlife, and conveniently close to notable Florida Keys restaurants.
This property boasts a private 107-metre dock for boat access, a heated swimming pool and spa, complimentary bicycles and kayaks, and high-speed 1 gig ATT fibre internet, with cleaning included in the rates.

Frequently asked questions about holiday rentals in Cudjoe Key, FL

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Best Cudjoe Key, FL holiday rentals with a balcony

Open Water Views |  32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape - Cudjoe Key, FL
9.0 2 reviews
Cudjoe Key, FL
29/08 – 03/09
357 €/nighttotal: 1785 € (5 )

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

2 4
apartment , Cudjoe Key
This waterfront holiday flat in the Venture Out community on Cudjoe Key offers direct open water views and convenient access to restaurants such as Square Grouper and Kiki's Sandbar, located within a 10-minute drive, with Key West being a 20-minute drive away.
This 80-square-metre holiday flat accommodates up to six guests across two bedrooms and features a fully equipped kitchen with stainless steel appliances, air conditioning, Wi-Fi, a swimming pool, jacuzzi, and a 35-foot seawall suitable for boats up to 32 feet, complete with a private fish-cleaning station.
July Discount. Waterfront, Dock ,Kayak, Paddleboard,golf Cart, Bikes, - Cudjoe Key, FL
10 16 reviews
Cudjoe Key, FL
29/08 – 03/09
326 €/nighttotal: 1630 € (5 )

July Discount. Waterfront, Dock ,Kayak, Paddleboard,golf Cart, Bikes,

2 4
resort , Cudjoe Key
This Summerland Key holiday home, part of the Park Place Waterfront Resort Villa, is situated approximately 19km from Florida Keys Beaches and 13km from Upper Sugarloaf Key, offering easy access to Bahia Honda State Park and other attractions; take advantage of the New Listing Discount.
Sleeping up to six guests in two bedrooms and one bathroom, the property boasts a fully equipped kitchen, in-unit laundry, a private garden with swimming pool and hot tub, plus free Wi-Fi – perfect for a relaxing Florida Keys getaway.
Oceanfront 2br Retreat | 35' Dock, Open Views, Boater's Paradise - Cudjoe Key, FL
9.6 53 reviews
Cudjoe Key, FL
04/08 – 07/08
530 €/nighttotal: 1590 € (3 )

Oceanfront 2br Retreat | 35' Dock, Open Views, Boater's Paradise

2 2
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.
Oceanside Home, Dock,kayaks,bikes,pool,fishing,107 - Cudjoe Key, FL
9.8 197 reviews
Cudjoe Key, FL
04/08 – 07/08
568 €/nighttotal: 1704 € (3 )

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

2 2
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.

Best Cudjoe Key, FL holiday rentals with parking

218 M² House ∙ 6 Bedrooms ∙ 14 Guests - Cudjoe Key, FL
10 1 review
Cudjoe Key, FL
19/09 – 26/09
567 €/nighttotal: 3969 € (7 )

218 M² House ∙ 6 Bedrooms ∙ 14 Guests

6 8
house , Cudjoe Key
This oceanfront property on Cudjoe Bay, offering panoramic Atlantic views, is located 32 kilometres from Key West and within 1.6 to 12.8 kilometres of local eateries.
This spacious 218 square metre holiday home accommodates up to 14 guests with 6 bedrooms and 4 bathrooms, featuring direct ocean access, a private dock, a heated beachfront pool, provided kayaks, and new memory foam mattresses in its king and queen rooms.
Charming Cottages, Dockage, Pool, Just Minutes To Key West - Cudjoe Key, FL
8.6 129 reviews
Cudjoe Key, FL
29/08 – 03/09
270 €/nighttotal: 1350 € (5 )

Charming Cottages, Dockage, Pool, Just Minutes To Key West

2 4
cottage , Cudjoe Key
This Summerland Key holiday home is situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, Venture Key, Venture Out Keys, and Out Key, offering easy access to these nearby islands.
The 73 square metre property sleeps four guests in two bedrooms and one bathroom, and includes a fully equipped kitchen, washing machine, barbecue, swimming pool, and parking, plus Wi-Fi access.
Family Retreat Ocean Front Pool - Cudjoe Key, FL
9.4 92 reviews
Cudjoe Key, FL
19/09 – 26/09
869 €/nighttotal: 6083 € (7 )

Family Retreat Ocean Front Pool

5 8
apartment , Cudjoe Key
This Cudjoe Key beachfront property boasts panoramic Atlantic views, a private 18-foot floating dock, and is situated approximately 32 kilometres from Key West and 24 kilometres from Bahia Honda State Park.
The four-bathroom residence sleeps up to 14 guests, features a heated 3 x 6 metre pool, six bedrooms with new memory foam mattresses in several rooms, kayaks for exploring Cudjoe Bay, and a large screened-in porch with dining for twelve.
**Turtle Cove Views @ Venture Out** 2br/2ba Cottage +35 Private Slip | 80 Pool - Cudjoe Key, FL
9.7 125 reviews
Cudjoe Key, FL
04/08 – 07/08
535 €/nighttotal: 1605 € (3 )

**Turtle Cove Views @ Venture Out** 2br/2ba Cottage +35 Private Slip | 80 Pool

2 2
cottage , Cudjoe Key
This charming cottage is located on Cudjoe Key, just a 15-minute walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to the island's natural beauty. The property has received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom cottage spans 79 square metres and comfortably accommodates up to six guests. Enjoy a range of amenities including a private swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, perfect for relaxing and enjoying your stay.
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