Resort holiday rentals in Estero Island

Hyatt Coconut Cove - Xmas (Dec 20-27 2026) Studio

Celebrate an unforgettable Christmas (Dec 20–27, 2026) in this luxury studio at Hyatt Coconut Cove. Sleeping four with a king bed and sofa bed, this refined sanctuary is perfect for a festive escape. Trade the winter frost for the soft glow of holiday lights over Estero Bay. Drift down the 1,000-foot lazy river or take the private boat shuttle to a secluded beach. Every detail is designed for holiday relaxation. Book early to secure this premium Christmas week getaway before it's gone!

Beachfront w/Balcony Pool 1bdrm Dwtn FtMyers Beach

Ocean/Pool view Diamondhead Beach Resort Ft Myers Beach 1 bedroom, Living room w pullout sofa, kitchenette furnished NEW POOL, towels provided Beach front,beach chairs, umbrella, volleyball court, workout room, free parking Great restaurant & bar indoors Grocery store less then a mile away. Downtown less than 1/2 mile, easy walking distance with shopping and restaurants. 10th floor overlooking pool & Gulf of Mexico. Great beach access. Fitness Center diamondheadfl website info on property

Beachfront 2BR/2BA Condo on Fort Myers Beach

Direct beachfront resort with perfect sunset views. Beautiful 2 bed, 2 bath condo, featuring washer & dryers, a full kitchen, & private balconies allow you to relax each day & enjoy a morning cup of coffee or evening glass of wine. Each unit sleeps 6 & has plenty of room for everyone to spread out. Located on the north-end of the island Be-Air Beach Club is close to all the shopping & restaurants. The resort also offers a pool and complimentary grills if staying in sounds good too!

Steps to Vanderbilt Beach + Dining, Pool & Kitchen

Escape to Vanderbilt Beach Resort, a family-owned beachfront gem in Naples, FL. Relax in condo-style suites with full kitchens and screened lanais overlooking the Gulf or gardens. Unwind by the heated swimming pool, play a match on the tennis courts, or dine steps from the sand at the legendary Turtle Club Restaurant. Just minutes from Mercato shopping and Delnor-Wiggins Pass State Park, it’s the ultimate mix of relaxation and convenience.

Beachfront Lani Kai Island Resort - Standard King

For nearly four decades, the Lani Kai Island Resort has welcomed guests from all over the world. The Conidaris Family has developed the Lani Kai Island Resort on Fort Myers Beach into the amazing and iconic property it is today. From the beginning, the hotel was the passion project of Bob & Grace Conidaris who wanted to create a fun, energetic place for both guests and the community.

Beachfront and Outdoor Pool | Pets Welcome Here!

Discover serene beach bliss & vibrant nightlife steps away! We offer unforgettable sunset views along with pool parties and live entertainment. Perfect for groups of friends, family or couples craving relaxation at this sandy beachfront resort.

4737 Jackfish St - 4 Bedroom W Den

Luxury Waterfront with Heated Pool & Gulf Access – Bonita Springs, FL Wake to Estero Bay views, sip coffee by the heated pool, explore Coconut Point shops, launch kayaks or bikes, and end the day with breathtaking waterfront sunsets.

Hideaway Waterfront Resort Suite A3

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

Hideaway Waterfront Resort GR A4

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

Hideaway Waterfront Resort Guest Suite A18

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

Hideaway Waterfront Resort GS(2) A37

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue.

Hideaway Waterfront Resort Suite A6

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue.